The 5 Types of Cheating and the Question Betrayed Partners Never Ask | Jim Sexton | E193

9 Sep 2026 · 1 h 29 min · 35 chapters

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In short

Jim Sexton (divorce attorney and relationship educator) discusses infidelity as a spectrum, then lays out “five types of cheating,” plus what betrayed partners rarely ask and how couples can reconnect before rupture.

Guest backgrounds

Jim Sexton is described as the “most famous divorce attorney in the world,” having handled over a thousand matrimonial cases and written two best-selling books (including “How to Stay in Love”). He’s also portrayed as an advocate for love after 25 years observing marriages.

Key claims

  • “Caught cheating” vs “confessing cheating” are fundamentally different.
  • Cheating includes more than sex: explicit photos/descriptions, and flirting inconsistent with the partner’s presence.
  • Many affairs are “punctuation marks” that reflect earlier disconnection.
  • Betrayed partners often ask “who/how long/how many,” but almost never ask the critical question: “What was I not giving you that you needed?”
  • Details of the affair usually aren’t healing; limited detail is better.

Notable examples

  • A New York prenup “weight clause”: for every 10 pounds gained, $50,000 less alimony; upheld despite being called “disgusting.”
  • “Granola” and “blowjobs” story from a client: small everyday attentions faded, then the husband had an affair.
  • “Vegas” as a setting for alcohol/flirting “big mistakes.”
  • “Revenge affairs” and the idea that “sex addiction” can be a convenient excuse rather than the real issue.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Understanding Cheating: Two Perspectives

0:00 to 1:06

Learn the difference between being caught cheating and admitting infidelity.

“At the beginning of this, you said to me, when someone has been caught cheating or when someone tells their partner that they cheated, those are two very different things.”

The Dangers of Losing Attraction

1:39 to 2:20

Explore how loss of attraction can lead to infidelity in relationships.

“One of the reasons people don't stay together, their sexual attraction goes away.”

The Weight Clause in Prenups

2:20 to 4:38

Discover the unconventional weight clause in a prenup and its implications.

“It's the one story I tell and the one story in the book.”

The Five Types of Infidelity

6:21 to 10:00

Learn about the five types of infidelity and their underlying causes.

“You spend a lot of time with people when you've represented them in a long-term divorce, protracted divorce.”

Flirtation vs. Cheating

10:00 to 14:00

Discuss the nuances of flirting and how it relates to cheating in relationships.

“But it's something about these little things we do for our partner.”

Defining Cheating and Relationship Boundaries

14:00 to 16:32

Explore the nuances of what constitutes cheating and personal boundaries in relationships.

“So just this one comes up all the time with my friends.”

The Five Types of Cheating - Part 1

16:32 to 19:38

Learn about the first three types of cheating including the freshly discovered soulmate and wake-up call.

“The first type is the freshly discovered soulmate.”

The Five Types of Cheating - Part 2

19:42 to 28:00

Delve into the last two types of cheating and discuss their implications on relationships.

“A lot of time alcohol is involved where somebody just screwed up.”

Exploring Infidelity in Marriages

28:00 to 29:05

Discussion on a friend's experience with infidelity and its perceived benefits.

“I have a friend who has an amazing marriage, Loves his wife.”

Cultural Perspectives on Cheating

29:05 to 30:32

Insights into Brazilian culture's acceptance of prostitution and its implications for marriage.

“So there are what's called termas, which means spa, basically.”
Show all 35 chapters

Understanding Sexual Needs and Desires

30:32 to 31:34

Discussion about varying sexual appetites and the complexities of relationships.

“or they have a kink that they're super into.”

The Psychology Behind Cheating

31:34 to 32:56

Exploration of the motivations behind cheating and the emotional consequences.

“But any behavior you engage in to prevent yourself from feeling what you would have felt if you'd done nothing at all.”

The Impact of Infidelity on Partners

32:56 to 33:59

Discussion on how infidelity affects both the cheater and the betrayed partner.

“How is that that much different from me going and playing blackjack for a weekend in Vegas?”

Questions After Infidelity

33:59 to 36:18

Identifying key questions that arise after a partner cheats and their significance.

“and how much it hurts even the person who cheated and how much it hurts the person they cheated with.”

Patterns of Discovery in Cheating

36:18 to 37:42

Discussion on the different ways partners discover infidelity and their psychological implications.

“The forgetting is harder to do than the forgiving, you know, but I think the forgiving is in the forgetting.”

Recovery from Infidelity

37:42 to 39:43

Exploration of the path to recovery after infidelity and the societal stigma surrounding it.

“Those are the things that two have in common, but that's where the comparison ends.”

Facilitating Honest Conversations in Relationships

39:43 to 42:00

Encouragement for open communication in relationships to prevent infidelity.

“ours where we could so easily share our experiences and our challenges and the things we have a hard time with, I think it's sad when people can't be honest about things that they're experiencing.”

Navigating Difficult Conversations in Relationships

42:00 to 43:58

Learn how to approach sensitive topics with your partner effectively.

“But if you say, I'm scared of swimming, I would work on that.”

The Implications of Opening Up a Marriage

43:58 to 45:51

Explore the complexities and potential fallout of non-monogamous relationships.

“There's in a lot of marriages, you need to keep the sex fresh.”

The Reality of Monogamy as a Practice

45:51 to 47:25

Understand monogamy not as a natural state, but as a disciplined practice.

“I only know one person who practices ethical non-monogamy consciously and openly and has found that to be conditions under which they are still able to sustain a successful monogamous relationship.”

Understanding the Consequences of Sexual Relationships

47:25 to 48:32

Recognize the inherent consequences that come with sexual relationships.

“When my sons got to a certain age, the age where, you know, sex might start being something to enter into their world.”

The Importance of Extreme Preparation in Success

48:32 to 50:45

Discover how meticulous preparation can significantly impact your success.

“over the years I had a period of eight years being single and now I'm recently single, I will tell you that I've turned down a lot of sex.”

Navigating New Relationships After Divorce

50:45 to 55:25

Learn best practices for introducing new partners to children post-divorce.

“I actually take that to my personal life as well.”

Personal Stories of Dating After Loss

55:25 to 56:00

Hear a personal account of navigating dating after a significant loss.

“the nature of romantic relationships in the same way that a 10-year-old does and certainly in the same way that a 17-year-old does.”

Family Dynamics: Navigating New Relationships

56:00 to 57:29

Learn how to approach family dynamics when a parent starts dating after loss.

“I got to send somebody to Vermont to get him.”

Dealing with Ex-Spouses and New Partners

57:30 to 59:28

Understand the complexities of co-parenting and introducing new partners to children.

“my sister who's a dentist and they said you know oh she's with a patient i said pull her out i need to talk to her so they pull out she's like what's the matter i said dad's dating gene she goes okay okay, who cares?”

The Role of Perspective in Divorce

59:29 to 1:10:00

Explore how different perspectives shape the narrative in divorce situations.

“Yeah, I mean, this is the kind of thing I see happen in divorce situations.”

Navigating Challenges and Self-Reflection

1:10:00 to 1:12:00

Learn how to process pain and embrace life's challenges positively.

“So sometimes your job is to create leverage and inflict pain that can be an educational kind of pain for a person.”

The Complexity of Dating and Relationships

1:12:00 to 1:16:20

Explore the challenges and dynamics of dating, especially as a public figure.

“He's amazing to my kids and to her and makes me super happy.”

Life Goals and Future Aspirations

1:16:20 to 1:19:50

Understand the speaker's perspective on life goals and future plans.

“require a lot of me, or my employees and my clients.”

Life Lessons and Wisdom

1:19:50 to 1:21:40

Hear valuable life lessons and insights gained through experience.

“I have 33 acres in the Catskills in the middle of the woods.”

Curiosity and Depth in Conversations

1:21:40 to 1:23:59

Discover the importance of curiosity and depth in meaningful conversations.

“I've done more, seen more, loved more, accomplished more.”

Curiosity and Podcasting Approach

1:24:01 to 1:26:28

Explore the host's deep curiosity and unique podcasting style.

“you want to ask me before we finish today?”

Gratitude and Impact of the Conversation

1:26:28 to 1:27:42

Reflect on the value of the conversation and its impact on listeners.

“that people are going to love and respect hopefully you're going to change lives i know i've learned a lot of things from you um on this show and again i've watched every clip you've ever done.”

Anticipation for Future Connections

1:27:42 to 1:29:08

Discuss plans for future meetings and personal connections.

“Like that was a conversation worth having where I feel invigorated.”
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Transcript

Automatic transcript. May contain errors.

0:00At the beginning of this, you said to me, when someone has been caught cheating or when someone tells their partner that they cheated, those are two very different things. That's like saying when you got fired or when you quit your job. Yes, you don't have a job. Those are the things that two have in common, but that's where the comparison ends. If I came home and said, oh, yeah, you know, there's lots of women I'd rather, I'd really like to have sex with, but I made a promise. I'm going to honor my promise, babe. Like, that's a terrible, terrible thing.

0:28Randall Kaplan:Are there groups of people or personalities who should not get married? People who are incredibly uncomfortable being alone. You shouldn't get married if you're that way. Even though marriage will probably be one of the most appealing things to you. Because it's, oh my god, I'm going to have a person and I won't ever be alone. I think that's actually a terrible reason to marry.

1:05Randall Kaplan:you're listening to part three of my incredible interview with jim sexton the most famous divorce attorney in the world and maybe the most famous attorney in the world in general he's handled over a thousand matrimonial cases written two best-selling books if you're in my office it's already too late and how to stay in love and has become one of the most watched voices on the internet when it comes to love relationships and why they fall apart here's what makes him different. He's not just cynical. After 25 years of watching marriages, he is one of the greatest advocates you'll ever meet for love.

1:35Randall Kaplan:He just happens to know exactly where it goes wrong, and today he's going to share it with us. James, welcome to In Search of Excellence. Thanks. It's great to be here. I really appreciate you having me. I was excited for this. One of the reasons people don't stay together, their sexual attraction goes away. I have a friend who will remain nameless will call him Mr. Smith. And Mr. Smith says to Mrs. Smith, if you don't stay in shape, the next Mrs. Smith will. And you've seen some crazy, and again, I don't, I said to him, dude, like, that's fucking nuts. You can't really say that to your wife. But I do understand what's behind it.

2:11Randall Kaplan:You know, if like you're in shape and you're attracted to someone and someone blows up, you know, and you don't like fat people, obviously you don't want to have sex with them. You've seen some crazy clauses in these prenups. Tell us about the weight clause. The weight clause. People love this story and it's true. It's a true story. It's the one story I tell and the one story in the book. People legitimately go, are you serious? Like, is that real? You know, like, and there's some crazy stories in my book, but, and in my media work, I've talked about some really crazy divorces without betraying any client confidentiality, But that is that prenup clause is the story that most people go with.

2:49That can't be real. But it was real. It's a real it's a real story. I represented a gentleman who was defending. I did not write the prenup. The prenup was like, I think, 12 years earlier. It had been written by a colleague of mine who was now retired. He was very wealthy and he was marrying a woman who was a model. And what he brought to the table is he was wealthy. And what she brought to the table is that she was very beautiful. And there was a clause in the prenup that for every 10 pounds she gained from the date of marriage, she lost$50 ,000 in alimony. She tried to set aside the prenup, that clause in the prenup, and get the full alimony.

3:29And I was defending the prenup as a contract. And I was successful in doing so. And I don't think it was great lawyering on my part. I actually didn't have to do much. The judge did most of the work because the law is very well settled in the state of New York and in most of the 50 states. She basically said, this is a disgusting provision. It's boorish. I don't know why you married him if he insisted on this provision. However, it's a contract. You both were represented by lawyers. You're both adults. You both understood what it meant. There's nothing in the record that would indicate you didn't understand.

4:08In fact, it's a very easy to understand clause. For every 10 pounds you gain, you lose$50 ,000 in alimony. It's not that complicated of a provision. It wasn't written in the legalized craziness. But the court upheld it. And people look at that and they go like, oh my God, you can put, and it's true, you can put any number of crazy things in a prenup. You can put how many days a week you're going to have sex. You can put all kinds of things. And there again, it's a question of how do you prove it? The weight clause was fairly easy to prove. She essentially had to have a baseline weight. And it said, this is what her baseline weight is.

4:40at the time of marriage. And then the metric of when does she, you know, I always thought as a lawyer, it was kind of a funny and crazy provision because if I was her, when I did the weigh-in at the time of the marriage, I'd have had pennies in my pockets and wore my heaviest boots. And then when I was doing the weigh-in for the divorce, I'd have been like a wrestler, like in the sauna, you know, with one of those sweatsuits on, you know, and then like really trying to shed as much as I could water weight wise. But, you know, she lost, I think she gained like 15 pounds or something like that. So she lost a fair amount of alimony, but she's still, this guy was a multi, multi-millionaire.

5:15She still got a very significant award under the prenup. And it wasn't unconscionable. It wasn't a basis to set aside the agreement. But would I recommend that provision to someone? I've never seen another one. I've never seen another one like that.

5:28Randall Kaplan:I hope you're enjoying this video so far. But before we jump back in, I want to know if you've ever thought about what you need to do to reach another level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lift and Seagate. And I also co-founded a company that today is worth more than$15 billion. I've been incredibly blessed in my journey. And at this stage of my life, I want to give back. I want to share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals.

6:00Randall Kaplan:I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions. And if you're a good fit, my team will reach out so we can build a game plan together. All right, now let's get back to the video. We're gonna talk about cheating now. Before we do, you've talked and written about the five types of infidelity, but before the portrayal, when nobody cheated, when no one was malicious, but something still died, you use the example of the wife quietly decides, blowjobs are inefficient and a husband quietly stops buying her granola neither names the drip but by the time the affair happens whichever of the five types it is is the real failure already 10 years old by that yeah i mean the blowjobs and granola story for me is the perfect encapsulation of the reality of how two people kind of unintentionally screw up their relationship because they just stop noticing each other and they stop actively trying to let the other person know that they're paying attention.

7:10And for those who haven't read my book or listened to it on Audible, basically the long story short is that I have been representing a woman in a very ugly divorce and we got all the way to trial and we were sitting outside. We'd spent a lot of time together. You spend a lot of time with people when you've represented them in a long-term divorce, protracted divorce. And she's a very successful woman, married to a very successful man. And we were sitting outside the courthouse after a lunch break. And she said, you know, I often in making conversation will say like, was there a moment where you realized you were getting divorced?

7:43And she said, yeah. She said, it's kind of an odd moment. She said, but there was this granola that I used to always eat with my yogurt for breakfast. And they only sold it at this Whole Foods near us. And my husband, he just always bought it for me. She was like, just right when it would be like running out, there'd just be a new bag she's like and she's like he never like mentioned it like it just was the thing he did like and i don't know that i ever thanked him for it she's like i i might have been like oh you got my granola thanks she's like but it was just this thing he did he didn't even like look for any good boy points for it you know he just did it and it always made me feel like kind of loved or whatever i guess and she said the reason why i know that is because one day i ran had a granola.

8:27And she's like, I kind of thought, oh, that's weird. She's like, but I left the bag because I thought, oh, maybe he hasn't noticed yet. She said, then like a week went by and he still hadn't bought it. And I thought, oh man, maybe this thing's on its way out. And sure enough, sure enough, it was. And sure enough, he ended up seeing somebody else. And I said to her, you know, because I thought I was very touched by that story, you know, and I said to her very seriously, I said, you know, was there anything like that that you did for him? and without even hesitation she said yeah blowjobs and i i literally spit my espresso across like i was sipping an espresso and i'm like it just was like something i have a movie she said yeah when we first got married like i even when we were dating like i used to get blowjobs all the time like it was just you know it took like three minutes and it like made his whole day like and he was like so happy about it i was kind of like yeah you know like it was fun to see him so happy and you know like it whatever it just made me feel good she's like and then at some point she's like i just you know i don't know i didn't do it as often and then it was like all right well look you know like i don't owe him a blow job like and you know what like i'll we'll have sex later when he gets home you know like from work and then we can both have fun you know it was sort of like hey we you know as kids we gotta do all this stuff in the morning like i'm not gonna again looking back she was like i'm not gonna waste that three minutes like you couldn't find three minutes while the kids are downstairs like really like but she said she's like it just stopped being something I was thinking of.

9:50I just was like, oh yeah, you know, kind of like the granola. Like, I owe you the fucking granola. And you're right. You don't owe him the granola. You don't owe him the blowjob. You're absolutely right. Nobody owes anybody anything. In fact, you don't even have to get married, you know. But it's something about these little things we do for our partner. I'm not saying a blowjob is a little thing. I've never given one. But having received them, I can tell you I've never received one that I wasn't absolutely thrilled. You know, like it really like blowjobs are like pizza. When they're good, they're amazing.

10:16When they're bad, they're still pretty good. So I absolutely think there's nothing small about that task as compared to buying granola, but it's a message. And the message is you're important to me. Your pleasure is important to me. Your happiness is important to me. Your joy and fulfillment is important to me. There are things I get to do for you and to you that nobody else gets to do. And I'm not going to take that for granted, you know? And I'm not going to take the attitude of no one's allowed to do this to you but me, but I don't really have the time to do it. That's very unfair. Like that's very unfair.

10:53If we've made a rule, I'm going to not have sex with other people in exchange for exclusively having sex with you. I feel like there is an obligation there. And as unromantic as that may sound. But if we have made a rule that we are only going to be each other's single sexual partner, then I feel we owe it to each other to take that role seriously and to try to understand each other's needs and meet them to the best of our ability. Does that mean that we owe each other that on demand anytime? Absolutely not. No, I would never say that. And I don't believe that. But do I think that we have a certain responsibility to each other, to the relationship?

11:31Yes, of course.

11:32Randall Kaplan:Cheating is like porn. It comes in many shapes and sizes. How do you define cheating and at what point has someone crossed that line wow i think it's a very personal i mean look i think we can all do sex with another person is cheating i think we can most of us agree that any sexual or quasi-sexual physical contact with another person is cheating sending another person explicit explicit intimate photographs of yourself is cheating sending a person explicit descriptions of things you'd like to do to them or have them do to you is cheating i think most of us would agree. What about you're married?

12:06Randall Kaplan:There's a hot woman online and you send her the flame as a DM. Is that cheating? In my definition, I think it depends on the intention and the nature of that relationship. If you have a relationship with that person, that it would be acceptable for you to basically what you're saying is you look hot. There are women in my life I could say that to, that it would obviously not be sexual. It was me sort of doing like a you-go girl for them. And then there are women that if I did that, it's clearly me flirting with them. I think flirting with another person in a manner that is inconsistent with the way you would behave if your partner was there is inappropriate and is a form of cheating.

12:47I happen to be what I would like to not call flirtatious. I would like to say I am charming. So, for example, I'm a heterosexual man, but I have a number of gay friends. So I'm not going to have sex with them because I'm a heterosexual man. But a couple of them are flirtatious with me and find me attractive. And I'm flirtatious with them because it's fun to be flirtatious with a person. I'm not gay. I'm not going to have sex with them. They know that and I know that. But it's fun to be fun and flirtatious with them. And because, again, they find me attractive. It's fun to me to be found attractive.

13:23And we sort of are playful with each other about it. It's a nice thing. It's the same thing there are women in my life that I would never have a sexual relationship with, but we're flirtatious with each other. Why? Because flirtation is fun. Would I do it in front of my partner? Of course I would. Yes, absolutely. Just like I think if my partner was flirtatious with someone in front of other people, I wouldn't have a problem with it. If I was dating a woman and she said, I'm going out with my girlfriends and we're going to flirt with boys and dance with boys and have them buy us drinks. And so I'm going to dress up in this very sexy way.

13:56And that's what I'm going to do. I would be fine with this. Go right ahead. If she said.

14:02Randall Kaplan:So just this one comes up all the time with my friends. So your your wife goes to a nightclub in Las Vegas. She's got a short miniskirt on. You can kind of almost see, you know, it's in there. Her tits are hanging out and, you know, she may say, you know what? I like looking good with my friends. But really, you like the attention you're spending the whole night with guys at your table buying drinks. Is that cheating not to me to me it would not be cheating i don't i don't like i don't like i don't like the idea of of showing too much of your body i think there are parts of your body that only your partner should get to see that's again my definition but do i think there's something fun about make-believe and about going out and being flirty and silly and fun like i think a lot of women that i know and a lot of women that i've dated that they're really not as much into the sex as they are the attention.

14:55And so if a woman can have the attention and not have sex, kind of totally fine with that. Like if she said, I'm going to put on a very skimpy outfit, not showing my intimate areas, but I'm going to show some cleavage. I'm going to dress sexy. Like I would dress if I was with you. I wouldn't want, by the way, I wouldn't want a woman I'm dating going out with me

15:18Randall Kaplan:dressed in ways that show most of her intimate areas. I don't, I wouldn't want that at all. But do I want to have a woman who dresses sexy when she's going, of course, there's something very nice about that. And I'm going to dress very nicely for her. That's a lovely thing to look at, wear a little shorter of a skirt and show a little of your body. If you have a beautiful body and you want to show it off, it's wonderful. I have no qualm with that. And you're going out with your girlfriends and you're being flirty with boys. Are you kissing them? Are you having sex with them? then we have a problem.

15:48But you're letting them buy you drinks and you're dancing with them. Again, are you grinding up a bit? I don't really like physical contact. But again, if you're just having fun and dancing and being silly and letting boys flirt with you and you flirt with them and you're having fun with your friends, I personally, this does nothing to offend.

16:06Randall Kaplan:If this is something you needed to do on a regular basis, I might start saying, hey, what is the need you're not getting at home? But if you're like, hey, once a year or a couple times a year, I just like to go out with my girlfriends and play. You know, it's like LARPing, like pretending that we're single and having fun. How is that hurting my relationship in any way? I just don't see it as a problem. OK, in your book, you talk about five types of cheating. The first type is the freshly discovered soulmate. Let's take these one by one and we'll summarize these so we can get through all five. Sure.

16:45freshly discovered soulmate is when someone it's the most to me the most painful and tragic which is someone comes home and says i've met someone else and i love them more than i love you period that's it is it is it real most of the time no i think it's like the siren song that drives you right to the rocks it's just that you're just dissatisfied in your relationship and you found this other person and you think that like the grass is greener on the other side of the fence

17:11Randall Kaplan:you know a man who leaves his wife for his mistress usually just leaves a job opening The second type is a wake-up call. The wake-up call for me is you didn't mean to cheat, but in making a connection with another person, it drives home to you that like, oh man, like I didn't realize how disconnected from my relationship I was. You just sort of, it's kind of like when you gain weight, you know, it's not like you go out to eat, you have a decadent meal and then you get up the next day and you're fat. That's not how it works. But like you make a series of bad choices over a period of time and all of a sudden your pants don't fit right.

17:45And that's usually how you know you've gained weight. Unless you're someone who's like, hey, measure what matters and I'm going to diligently measure my body mass and all that stuff. Very often people don't realize they've gained weight until they've gained some weight, you know? So it's the same thing. It's kind of a wake-up call of like, oh, you know, like this, like I didn't realize this thing was as bad as it is. Now, again, that can sometimes lead people to say, okay, wait a minute. I don't want to give up my marriage. Like that's just, we got really far from each other. What do we do now?

18:11How do we reconnect? This is like, it's not the beginning of the end. It's the end of the beginning. Like, we got to figure this out. You know, just like people in sobriety circles, like relapse is part of recovery. You know, a lot of people, like when they relapse, that's the start of their sobriety. You know, it really is that like you had to make that mistake in order to move to the next stage of your recovery.

18:30Randall Kaplan:Third type of cheating that you've identified, which happens when a lot of times when you have a lot to drink, would be the big mistake.

18:43Randall Kaplan:I hope you're enjoying this video so far, but before we jump back in, I want to know if you've ever thought about what you need to do to reach another level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lyft and Seagate, and I also co-founded a company that today is worth more than$15 billion. I've been incredibly blessed in my journey, and at this stage of my life, I want to give back. I want to share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals.

19:15Randall Kaplan:I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions. And if you're a good fit, my team will reach out so we can build a game plan together. All right, now let's get back to the video.

19:39Just a mistake. Yeah. This is just something dumb. You just did something dumb. A lot of time alcohol is involved where somebody just screwed up. They took something too far. They were in Vegas with buddies. They were away on vacation with friends. They were flirting with a coworker at the holiday party, something. And they just fucked up. They just made a mistake. It was like a one-off. It wasn't supposed to mean anything. It just happened. Sometimes it doesn't have to have alcohol or drugs involved. that can just be that you're being flirty with somebody and they were being flirty back. And the next thing you know, you just took it too far and you didn't realize how far you took it.

20:16And you ended up kissing the person or you ended up doing something with the person. And it's not like it's just, you just made a mistake. Like you just made a mistake. Like sometimes people just make a mistake. I refuse to accept that everything means something. I think sometimes people just make a mistake.

20:37Randall Kaplan:There's all these marketing slogans to get people to come visit various cities. And one of the ones about Las Vegas is what happens in Vegas stays in Vegas. That's definitely not good for people's marriages. I see a lot of stuff going down in Vegas. Yeah, especially, I mean, you know, STIs don't actually stay in Vegas. They come home with you. But yeah, I mean, yeah, the choices people make. I love Vegas. I go to Vegas a few times a year to play blackjack. I enjoy it very much. I actually just booked my next trip to Vegas. and I go for a weekend. I bring the amount of money I'm prepared to lose and then I usually go about losing it.

21:13But I have a great couple of days and really enjoy it. And they're always happy to invite me back and give me a comp room because I help them leave the lights on. But you know what? Like that's some people spend a certain amount of money to sit on a beach. I like playing blackjack. I find it meditative. I've never bet anything I couldn't afford to lose and I've never made terrible decisions in Vegas. do I go there and behave a little irresponsibly and drink a little more than I normally would eat a little more decadently than I normally would spend money like it doesn't mean anything tip wildly absolutely and you know what I've yet to ever regret a trip to Vegas

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21:48Randall Kaplan:the fourth type of infidelity that you've mentioned you call the push out of the closet yeah that's increasingly less common because now there's less of a stigma attached with same sex relationships But before marriage equality, and when, you know, 25 years ago when I started, you know, being gay, lesbian, transgender, like there was more stigma attached to these things socially. So there were a lot of particularly men, but also some women who were, you know, in the closet. And they were secretly gay or lesbian, usually gay men. And they were raised in religious households where they couldn't be open about their sexuality.

22:26and, you know, they married. They married someone of the opposite sex, you know, in the hopes that either A, they could pray the gay away or B, that they would find fulfillment in this relationship. But in reality, you know, trying to deny your sexual orientation is like trying to push a balloon underwater. It's not going to be successful. It's going to just pop up in other strange, difficult ways. And so I've had a number of cases where people, you know, cheat with same-sex partners because that is their sexual orientation and they weren't really being honest with themselves or others about it.

23:01That's hard. It's hard. It's sad. What I thought that would be like for clients and what it actually seems to... It's never happened to me, but I've seen it happen to clients. And I remember thinking, oh, that wouldn't be so bad if a woman was in a relationship with me and she said, look, I'm leaving you because I've decided I like to have sex with women, I would be like, okay, like I don't serve that at this restaurant. Like I don't, like that's, I can't, I can be lots of things, but I can't be a woman for you. So if that's what you like, I guess this is over. Whereas if she left me for a man, she's saying, I want one like you, but better than you or different than you.

23:43And that feels very painful to me. You know, that's much harder to deal with. It's like, oh, I want the same equipment, but better or different. So, you know, but in reality, that's not what happens. In reality, there's very often really hurt feelings there of like a feeling of you knew this about yourself and you lied to me and you didn't tell me. And that's hard because when you talk to and represent people who've had to make that choice, it's very often that they wanted it to not be true and hoped it would not be true. And they, or they were part of a family or a religious community or a culture where they kind of couldn't express who they were.

24:21So they lied to themselves and then they lied to the other person by proxy. It was very rarely that they were like, I'm going to deceive this person. It's very rarely that. It was really that they were having a very difficult time with their own sexuality. Thankfully, this is something I'm seeing a lot less because we live in a society now where I think gay and lesbian individuals don't really experience the level at all, anywhere near the level of discrimination and prejudice that they did for many years.

24:47Randall Kaplan:The fifth type and last type of affair that you've identified is called the revenge affair. Yeah, I mean, that's increasingly more common, thanks to the proliferation of social media and the way we've sort of weaponized men and women's relationships. That is that your partner cheated on you, or your partner engaged in some kind of betrayal or infidelity of you, and then you're like, okay, I'm owed one now. You know, like fighting fire with fire. Oh, you lied to me? I'll lie to you. Oh, you hurt me? Okay, I'll hurt you. I see it a lot. It's unfortunate. You know, we don't fight fire with fire. We fight it with water.

25:20It's literally the opposite. You do not fight fire with fire. Like someone hurt you by betraying you. So now I'm going to hurt them by betraying them in the same fashion. Like that's that will not make you feel better. It will make the other person feel worse. And that might make you feel better momentarily. I don't really know. I haven't found that to be the case. But it's very common when someone cheats on someone and then they try the path of repair, there's rupture and then they try the path of repair, but they don't really do the work, that often can lead to this person sort of harboring some resentment and then engaging in an infidelity of their own.

25:59Randall Kaplan:We talk about drug abuse, drinking too much is reasons why people split, but sex addiction is not something really people talk about a lot and it's very prevalent. In fact, in the United States, it's estimated that roughly 3 % to 6 % of adults, That's 10 to 20 million people suffer from sex addiction. And we talk about worldwide global population. That's 150 to 350 million people. Where does sex addiction fit in into the reason for divorce? And you see that a lot in your practice? Yeah, I mean, I don't, I'm really fuzz beyond, I know that there is a phenomenon that is legitimate of sex and love addiction.

26:38But I think a lot of people, when they get caught cheating, their responses to say, oh, I must have sex addiction. That's why I did this. I don't know that that's honest. It's sort of a way to not do the hard work of really trying to deconstruct how you got so far from each other that you lost the plot. It just makes it, oh, I have a problem. It wasn't us. I, it was me, just purely me. It's purely me. I have an illness. I have an illness. I have sex addiction. So our marriage is perfect. Everything's perfect. But the nefarious creature of sex addiction snuck in and now I just have to find the cure and then we'll be good I'm going to go do these 12 steps or I'm going to go away for 30 days and I'm going to come back and I'll have got rid of the poison and now we're good I don't think it's honest I I think that it's a convenient catch-all category that we can throw at a multivariate problem and it's listen I wish the world was a little easier sometimes like I wish the world was like pro wrestling with good guys and bad guys and you knew who was a bad guy because the evil music comes on when they walk in and you know who was a good guy because the inspirational music came on when they came in.

27:43It's not how the world works. I've represented victims of domestic violence and perpetrators of domestic violence. I've represented people with substance abuse issues. I've represented people married to people with substance abuse issues. I've represented the cheater and the cheated on. I can tell you, it's just hurt people hurting people. It's all it is. Like it's just human beings, human emotional complexity, people trying to figure it out. That's all.

28:02Randall Kaplan:I have a friend who has an amazing marriage, Loves his wife. Wife loves him. Three amazing kids. They travel together. He's truly, truly happy with her. But he knows somebody who knows somebody. And there's a process which you have to get in and interview with somebody. And once or twice a year, he'll meet a woman while he's traveling. It's very safe. They don't call it prostitution, but I guess in some ways it is. He pays her. These are high-class women. They're beautiful women. And he has sex with these women. and he goes back to his wife she doesn't know and if he believes it's good for his marriage are truly it is it true that content couples really don't cheat i don't know that i'm qualified to answer that except to say that most of the couples that i meet it's because their marriage has catastrophically failed so i i don't know that i'm the right sample to answer that for you what i will say is having been part of the brazilian jiu-jitsu community for many years i've spent a lot of time in Brazil.

29:04And in Brazil, prostitution is legal. It's restricted, but it's legal. So there are what's called termas, which means spa, basically. And there's what's called grata de programas, which is like, it means girls of the program. And it's basically like a strip club. Like you go into a strip club and, you know, these women are dancing and they're beautiful and they're scantily clad. But the difference is, is that you then can pick one or two or three or as many as you'd like and go up to a room and you get to have sex with this person. I know a lot of men who this is just part of their life. They jokingly refer to it as the term is my cousin's house.

29:39Oh, I have to stop at my cousin's house after work. I'll be home late because I'm going by my cousin's house. And it's an open secret. You don't say, oh, yeah, I'm going to the termist. No, you just, oh, yeah, I got some things to do at work or whatever. And then you slip out and you go in. This is something you take care of. I know a lot of men that say, yeah, it's been really great for my marriage because, you know, there's like, I love my wife. I have a family with her. I enjoy sex with her, but it doesn't have like the variability. And it's, there's things I respect and love my wife too much to do with her in a sexual context.

30:11And it would be difficult to make that disassociation where it's like, you know, I'm going to have this like crazy sex with this person and be like, all right, let's go downstairs and hang out with the kids. Like, it would be hard to do that. So they, it has a place. I don't think all of us are built exactly the same. I think some people have a voracious sexual appetite. Some people have less of one. Some people have, they want really raucous, crazy sex, or they have a kink that they're super into. And some people are just very satisfied to have, you know, like, you know, just enjoyable sex. Like that doesn't have to be, you know, it doesn't have to be fireworks and craziness.

30:44They don't need like, you know, kink. They're just sort of satisfied with what they have. I just don't think it's one size fits all. And I think that in relationship, do I know people who have successful, happy marriages and cheat? Yes, of course. I think most of us probably do if we're being honest. I know people that are like super, super healthy in their eating and their physique. And they, every once in a while, will go like in their car and order like a shit ton of McDonald's and just house the stuff. Like, and they would never tell anybody that they do it. And they do it almost with a sense of shame because they know that this isn't good for them and they know that it isn't a good thing to do.

31:19But it scratches some kind of an itch in them that they don't really understand. I get that. Do we all have things in us that we don't completely understand and that we don't know why we need. Look, what's better? Of course, we know what's better. What's better is to try to figure these things out in yourself. You know, what is addiction? But any behavior you engage in to prevent yourself from feeling what you would have felt if you'd done nothing at all. You know, I don't like how I feel right now. I'm gonna pick up my phone and play with it. I don't like how I feel right now. I'm gonna watch some pornography and masturbate.

31:50Like, I don't like how I feel right now. I'm gonna have a couple of drinks or I'm gonna smoke a joint. A lot of it is I don't like how I feel right now. What's the right thing to do there? It's the hard thing. Why? What am I feeling right now? The only question worth asking in therapy is what am I afraid to feel? Why am I afraid to feel it? I genuinely believe that there's value in being uncomfortable, figuring out why is this so hard for me? Why am I so uncomfortable right now? But do I understand the human desire to like things hurt right now and I just want something that feels good or tastes good and takes me out of my brain for a second and just gives me a moment of pleasure.

32:26Of course I understand.

32:28Randall Kaplan:I'm human. I understand that completely. So can I judge people for feeling that way? I don't think I have a right to judge people for feeling that way. Would I say that that's a good solution to the problem of being sexually dissatisfied in your relationship? But like if your friend has a satisfying, happy relationship with his wife and she feels loved and valued and he feels loved to her and he feels valued by her, And this is something he just goes and does every once in a while to just get something out of his system. How is that that much different from me going and playing blackjack for a weekend in Vegas?

33:03Who is it really hurting? I know we can attach all kinds of morality to it and say this puritanical way that we've, and again, I'm not pissing on that. I don't know. I'm not qualified to be anyone's moral compass. I'm not a particularly religious person. I'm not a particularly puritanical person. I've had sex out of the bonds of marriage. I'm sorry if that's breaking news to anybody. But the truth is, like, do I understand that? Sure, sure. If someone did that to me in relationship and I never knew about it, would it hurt me? Probably not, I guess. But if I found out about it, would I be very hurt?

33:39I would be very hurt. So if his wife found out, how would she feel? I can tell you, representing people who've been, you know, their partner has cheated on them, that it's incredibly painful for them. If anything will cure you of the desire to cheat, it's spending time with people who've been cheated on because you just see how much it hurts them and how much it hurts even the person who cheated and how much it hurts the person they cheated with. It's just nothing but victims and victims and victims and the whole damn equation. And for what? For a momentary rush of friction. Is the juice worth the squeeze?

34:14I don't know. You spend enough time with that pain. Is heroin probably really good? Probably awesome. them. I don't know. I know people that have lost their kids so they can feel it. I've never tried it personally, but it must be something to it. People love it. You know, am I going to go try it because people, you know, rave about it? No, no. Because I see the cost. I see what it creates in people. Like it's not, it's not a victimless thing.

34:38Randall Kaplan:When a betrayed spouse finds out that they've been cheated on, there's four questions you've said that people ask, but there's one critical question that a betrayed spouse almost never asks. So the first question they ask is, who is she, how long, how many times? Oh, yeah. Yeah. Yeah. Yeah. People think that they want the answer to those questions. What's interesting I've talked about before is that the questions men ask and the questions women ask are different. The first question most men ask is, did you sleep with him? The first question women ask is, do you love her? And I think that tells you almost everything you need to know about men and women.

35:15Yeah. I mean, when, how long has this been going on? Because I think what they're trying to do is categorize it. They're trying to figure out, okay, does this mean something? Like, is it a one-off or has this been going on for a while? Am I a fool? Did I miss something? Like what happened here? Like, was it just a dalliance or was this like a thing? Did you do everything with this person or just a few things? Like, was it, is it better than us or was it not better? What does it mean? Where do I put this? Are we over? Did you find someone you're in love with or is just this that you did this thing like will i ever be able to trust you again i mean these are the kinds of questions that people i think want think that they would feel better if they knew like oh if you tell me i want to know all the details so i can heal i i i do not think that that's a recipe for healing i think you'll never get that out of your head ever again and i think that it it i have not seen the people i have seen come back from infidelity, recognize the conditions that created it, apologize for the pain that it caused, and then try to find a way to move forward in a more productive way.

36:16And to some degree, the forgiving is in the forgetting. It's hard to do. The forgetting is harder to do than the forgiving, you know, but I think the forgiving is in the forgetting.

36:25Randall Kaplan:So if a spouse finds out that you cheated, you tell a spouse that you cheated, is it your advice that you should not give the details of what actually happened because somebody... That's my, yeah, that's my advice, and I'm not a mental health professional, but my advice is that you do not get into the details. You give the level of detail necessary in order for this person to have some basic understanding as to whether this person's going to show up again or whether this person's someone you interact with regularly or whether this was just sort of a one-off thing. But I don't think anything more than that is productive.

36:56I don't think it's helpful. I think people think they want the details, but they don't.

37:02Randall Kaplan:But the second question that they ask is, do you love her? Yeah, because that's really the core question. Because the core question is, if you love this person, do you still love me? Like, have I lost your love? Like, is your love now this other person's property? Like, has your love been taken from me? Did you give it away to someone else and take it from me? Like, and I think that's a very serious question. And that's one you really have to try to answer. You owe it, I think, to your partner to be able to answer that question. And by the way, at the beginning of this, you said to me, when someone has been caught cheating or when someone tells their partner that they cheated, those are two very different things.

37:41That's like saying when you got fired or when you quit your job. Like those, yes, you don't have a job. Those are the things that two have in common, but that's where the comparison ends. Like those are two totally different things. Getting fired and quitting are two totally different things. Getting caught cheating and going to your spouse and saying, I need to tell you this very painful thing are two very different things. Because one of them, you're doing it for some reason, whether it's that you believe confession is good for the soul or whether you really just can't live with the guilt of it or whether you believe it's necessary to say this to this person so they could see how far from shore your relationship has gone and that if we need to either fix it or this thing is over.

38:22I think those are very different things than if you get caught.

38:24Randall Kaplan:So the third and fourth question, the third one's why. And the fourth one is, what do we do now? I mean, why is the hard one to answer? And I think it's a long conversation you have to have with yourself and with your partner and ideally with the assistance of third-party professionals. Where do we go from here? I think it's the end of the beginning or the beginning of the end. That's what you have to look at it as. There are punctuation marks in relationships. There's the thing and everything after it. There's, we got engaged, we got married, we got a kid. You know, these are punctuation marks.

38:55I think an affair is a punctuation mark. We've unfortunately created a culture where, although infidelity is incredibly common and has been part of the world for thousands of years, I think that I've jokingly said that I think infidelity was invented probably 30 seconds after monogamy was invented. You know, probably some caveman came out of the cave and stumbled right into another cave, you know. But the truth is that we've created a world where you're not really allowed to talk about recovery from infidelity. Look at when people cheat, how much people are pilloried for taking someone back after cheating.

39:29And I think that's a very unfortunate thing because there are a lot of couples that come back from infidelity, but you have to do it in silence to some degree.

39:38Randall Kaplan:And I think it's always unfortunate when people suffer in silence unnecessarily in a world as connected as ours where we could so easily share our experiences and our challenges and the things we have a hard time with, I think it's sad when people can't be honest about things that they're experiencing. There's this black and white feeling among a lot of people. You cheat, so it's 100 % your fault. It has nothing to do with your partner. But the one question that almost never comes up is, what was I not giving you that you needed? Right. Well, and I understand why it doesn't come up because it's considered very blaming the victim to some degree.

40:14Like, well, I wouldn't have had to cheat if you blah, blah, blah, blah, I think that's a conversation a person has to have at some point with themselves and with each other. It's a painful one. But it's like, how did we create the conditions where this occurred? Because when we started this thing, we weren't in that place. So how did we get to this other place? Like, I'm a fan of way before any of this happens, any cheating happens,

40:36Randall Kaplan:having painful, difficult conversations, or even just mildly challenging ones. I know it would not be pleasant if I'm in a monogamous relationship And I say to a woman I've been dating monogamously for a period of time, hey, babe, I'm starting to get a wandering eye. I don't know why. I was very satisfied in our relationship. But lately, I've been feeling myself like feeling more flirtatious. I'm looking at more pictures on Instagram of other women. I don't want to. I want us to keep the spark we have together. But I just want to share with you openly, that's something I'm experiencing right now.

41:10And I'm not sure if it's something in me or something in our relationship. And I don't know what to do with it. That's honest. It's honest. Hard to say. Hard to hear. But I think it would be good to create conditions in a relationship where you could hurt each other a little so you don't hurt each other a lot. Because that's the truth. You feel how you feel. You can wish you felt otherwise, but you feel how you feel. You might be able to explain why you feel how you feel. You might not be able to explain. I can't explain why egg salad is gross to me. Some people love it. I can't, I don't. I think it's gross.

41:48I can't explain why if you said to me, but Jim, break it down. Help me understand how we got here with the egg salad. I can't. I've never liked it. I don't like it. I don't like how it smells. I don't like how it feels. Sorry. Jim, we got to work on this. We got to get you to love egg salad. You won't, I promise. It won't. It won't happen. Like it's, I feel how I feel. But if you say, I'm scared of swimming, I would work on that. I work on that. That's how you feel. I'm not going to do any favors by going, what do you mean you're afraid of swimming you're afraid of swimming you know how many people swim are you kidding little kids swim dogs swim what are you afraid of swimming that's stupid oh okay great i feel better now like no that's not how it works there's some things you can work on and you can say okay what's going on with us what's different like i just think you before you even have to get there that difficult conversation you can try to just be a little more open about what you need and what's changing something's changing you know and again do it in non-defensive ways.

42:45If you see your partner down and you go, you know, why are we having sex as much as we used to? You are not off to a good start, brother. That is not going to go well, that conversation, because she's going to go, well, you're never home anymore. Well, I'm not home anymore because I'm working. You're not spending any less money. Well, I'm not spending less money because I'm lonely. Well, you're lonely because I'm like, now we're off to the race. Whereas if you went to your

43:03Randall Kaplan:partner and you said, you know what I was thinking about the other day? I was just online. I was on Instagram and the thing came up for that little place in Bodega Head. Remember when we went and We stayed in that little bed and breakfast. And we didn't even leave the bedroom for like a day. I was just thinking about that. That was one of the best days of my entire life. That was so fun. You know, I know lately we haven't been as connected in that way. But God, you're still like the prettiest girl in the world to me. And I love when we feel connected like that. I just love that feeling we have when we're that physically connected.

43:35Okay, now we're going to get somewhere. Because what did I do? I brought you back in memory to a place we were both really happy and loved each other. And then I said to you without blame, hey, I missed that. Isn't that nice? And now how can we recreate that? How can we get back there? How can we be in that place together again? That's to me, that's conversation worth having.

43:58Randall Kaplan:There's in a lot of marriages, you need to keep the sex fresh. I mean, we've kind of talked about this where a lot of people think being married in a relationship with the same woman for 30 or 40 years, if you're a man and vice versa, is not a natural state. But a lot of couples that I know and friends will jointly agree to bring someone else into the bedroom with them. And it happens in a nanny context. You know, there's a cardinal rule with, in a lot of homes, never hire a good looking nanny who lives with you. That's just generally not a good recipe for a healthy relationship. And then there's people who will bring a third person into the sexual bedroom.

44:38Randall Kaplan:Have you seen a lot of that in your practice? Because in my experience with friends, I've never done it, but in my experience, I mean, I thought about it, but I've never done it. In my experience with friends, it almost never works out and often destroys marriages. Yeah. I mean, I'm the wrong guy to ask because I'm a divorce lawyer. So I'm sure there are plenty of people, or there may be plenty of people that open up the marriage or have ethical non-monogamous relationships and just never end up in my office. But I see lots of people that did it and then ended up in my office. But I'm a divorce lawyer.

45:10So, you know, I kind of like, I have a friend who's an oncologist. And if he called me and he was like, dude, everybody has cancer. Like everybody I met today has cancer. I'd be like, great, you're an oncologist, dude. Like people come to see you because they have cancer. Like if you were a cab driver, you'd meet a bunch of people that don't have cancer. Don't worry. Like it's, you're not seeing a representative sample, right? So I, of course, I see a lot of people who the Hail Mary pass of the unsuccessful relationship is let's open up the marriage or let's bring in that girl into the bedroom with us or let's whatever.

45:40And there's people that, you know, that's what you do because you're like, yeah, we're not happy. We're not satisfied. Does that mean you couldn't have figured out another path? It's an unfalsifiable premise to say, well, you maybe could have done different or done better like you did what you did. So I don't know. I only know one person who practices ethical non-monogamy consciously and openly and has found that to be conditions under which they are still able to sustain a successful monogamous relationship. I know a lot of people who tried to open up the marriage and it was unsuccessful and ultimately they ended up splitting up.

46:22I've seen that personally in relationships, not in my own, but in relationships. And I've seen it professionally a ton. But again, the latter, I don't think is a fair thing to talk about because of course I only see the ones that ended in divorce. But in my personal life, I've seen a lot of people where it just didn't work out for them.

46:39Randall Kaplan:I don't know that monogamy is a natural state, but there are lots of things that are not a natural state that we put value in, you know? It's a discipline, you know? And I think that there's value in discipline. and I think that monogamy is a practice. It's not a natural state. It's a practice. You know, having a fire in your fireplace isn't a natural state. Shit's just not on fire in your house, you know, but you light fire in your house. Why? It's for warmth or because it's nice. Like we don't need it for warmth now. Now it's just because it smells good and it's nice. Okay, but that doesn't mean it doesn't have value.

47:18Like I think monogamy, there were reasons for monogamy

47:21Randall Kaplan:And now there are slightly different reasons and some of the same reasons for monogamy. When my sons got to a certain age, the age where, you know, sex might start being something to enter into their world. I think it was their early teens, probably. I remember I was like, what speech am I going to give them? Because the speech I got was, you know, you know what sex is? Yeah, don't have it unless you're married. Okay, that works great. Like that's, you know, abstinence, that did not play out, right? So I remember thinking a lot about it. and I remember the conversation I had with each of them individually was, there's no such thing as sex without consequences.

47:55But all sex has consequences. Period. Anyone who tells you that there's such a thing as sex without consequences is lying to you. Like, all sex has consequences. Sometimes those consequences are serious. Pregnancy and STI, you know. But more often, they're changes to the relationship. Changes to the power dynamic in the relationship. Changes to your feelings about each other. changes to the way that each of you relates to each other and to the people around you, new risks, new challenges. So just don't think there's such a thing as consequence-free sex because there isn't. I think I stand by that lesson.

48:31Randall Kaplan:I'll just tell you that as a single man, over the years I had a period of eight years being single and now I'm recently single, I will tell you that I've turned down a lot of sex. A lot of my friends would not do that because the consequences and the responsibility afterward. I live in a small community. I want to be respectful. I want to be truthful with people. It just is not worth complications that come after that. But I want to talk about, you're a great lawyer. You're one of the most respected, famous divorce lawyers in the country. One of the things that's made me very successful over the years is something called extreme preparation.

49:08Randall Kaplan:I practice it. I preach it. I'm always the most prepared person in the room. How important has extreme preparation been in your success? It's everything. It's everything. It's 100%. The story I tell everybody is growing up as a kid, my parents used to have barbecues. And when they had barbecues, my mom would go out and buy all the ingredients, chop them up, marinate them, make a beautiful marinade for them, the whole thing. My dad would put it on the grill, take it off the grill, and everyone would say, Noah, you're such a great cook. And I used to think that was hilarious because my mom did 90 % of the work, which was the preparation.

49:39Like by the time I walk in a courtroom, the fight's over. It's just like when you're a boxer, you walk in the ring. The fight's over. Like most of the fight was the prep. Most of the fight was the organization, identifying leverage, cultivating leverage. Like the preparation is everything. You know, there's a line in the film, Batman Begins, where he says, you know, the will is everything. The training is nothing. The will is everything. Like the training, I don't believe in luck. I believe in training. Like, and I, it's reps for me. It's always been reps. Like I outwork most people. And I also work smart and efficiently.

50:18I don't waste a lot of effort. I learn, I'm very quick to adapt to change and recognize change and adapt to it to incorporate technological change into my practice. I am very methodical and organized. You could, in my office, you could perform surgery on any service without fear of infection probably because I'm very, very thoughtful and organized. An organized desk is a sign of an organized mind. And so everything I do, I try to be meticulously prepared. And I think it's almost all of my success is a function of preparation. I actually take that to my personal life as well. You know, I get up in the morning and I follow a very strict routine for the first few hours of every day.

50:57I get up, I have my espresso or pu-er-tea and I, you know, don't check my email immediately. I make a point of engaging in my body practice, which is usually either weight training or jiu-jitsu or peloton or some you know cardio and then i sit in a sauna or a steam room and i stretch and i have a stretching regimen that i do when i'm in there but it's also a time where i am preparing for the day mentally i'm honoring myself my body my physical state i'm doing something for me first so that i can be there for everyone else effectively but i start my day by honoring myself and honoring my body and the instrument that I have with which to do all of these things.

51:40And then I go about in a focused way taking on each of the tasks. And I have five different Google calendars and a bunch of different to-do lists. And I check things off. I believe in zero inbox theory. By the end of every day, my email is empty. My text messages are empty. You know, even if it's just a quick response of, thank you for sending this email, I'll be in touch with you tomorrow. That way everything is thoughtful and organized. That's always how I've done things. and it has been the secret to my success 100%.

52:08Randall Kaplan:One of the things about divorce that comes up is having new boyfriends or girlfriends after you get divorced. Sure. In my first marriage, my first wife was amazing, respectful. I gave her the same respect. When we had a boyfriend or girlfriend, we went to them and we said, okay, we're going to introduce the kids. We waited a prescribed six to 12 months. My second marriage, unfortunately, my soon-to-be ex-wife has not followed that routine and introduced her boyfriend, who we'll talk about in a minute, who has been unable, according to the newspaper, to sustain long relationships. As have people that I've spoken to, he's had relationships with, introduced her boyfriend after three months against the advice of everybody, including the most recognized child therapist in all of Los Angeles who speaks all over the world.

53:00Randall Kaplan:What have you seen, who has also explained to both of us and her that doing so today will likely cause some material damage later in life that they won't be able to see and that will not manifest itself today. What have you seen in your own experiences? How long, in your opinion, should people wait before introducing someone new to their family or their life? Yeah, it's a great question. I don't claim to have, you know, an authority on this. So I think it is something that would be best left to childhood psychologists and mental health professionals who specialize in children. But I will say in my practical experience, I always encourage clients and in our settlement agreements, I always include language that is not tied to a specific duration, but is instead tied to the concept of you would not introduce children to a partner unless and until it is a serious relationship.

53:56And I define a serious relationship as one that is likely to lead to cohabitation or marriage within the next three to six months. So there are times where people meet and fall very deeply for each other, and they're going to very quickly cohabitate or marry. Now, again, if you're the kind of person that has a pattern of relationship instability, you would do well to not sign up for something that you're introducing your children to if you have a pattern of relationship instability. But if you are someone who has always been a quick steady and who has not had a high number of relationships and you've met someone and you feel very strongly about them and you plan to marry them in a short order or cohabitate with them in short order, I think that there's value in rather than hiding that and trying to live your life in a fashion that hides that from your children.

54:47I think that's challenging. I would also say the additional complication that many people have, it sounds like the situation you're describing is different because this person may not have already been in the ecosystem of your family. But more often than not, people take up with people who are in their ecosystem. So, you know, the kids have already met this person because they're a family friend or they've met this person because it's a parent of one of their classmates or one of their teammates from their baseball team. And so they've already met the person. What you're really talking about is I'm going to introduce them as a romantic partner.

55:17And that, depending on the age and stage of your children, you know, I think it can be handled differently. I think a four-year-old doesn't really understand the nature of romantic relationships in the same way that a 10-year-old does and certainly in the same way that a 17-year-old does. You know, I will tell you very quickly, I know we don't have unlimited time, but when my mother passed away 10 years ago, about seven months after she passed away, my father called me and he had a very serious tone in his voice and it worried me because we'd just been through this really difficult thing and we were just sort of really recovering as a family.

55:54And I was talking to him and he was like, you know, it's been really hard with your mom gone. And I'm thinking, oh my God, he's depressed. I got to send somebody to Vermont to get him. I got to figure this out. All right, I'm going to buy him a place in the city and I'll keep him near me. And then, you know, because he lives in Vermont and he's like, you know, and my mother and father had this friend named Jean who lived down the street and her husband died some years ago and my dad and she would walk the dogs together and stuff. And when my mom passed, she was a wonderful support to my mom. She's a neighbor and a friend.

56:25And after my dad, after my mom passed, she would spend a lot of time with my dad, you know, like just, you know, giving him companionship. And he was like, you know, Gene's been such a great support. And I was like, well, it's good, dad. You have people who care about you. You have people that love you. Like, it's good. You know, if you're having a hard time, it's okay. You were married to mom for 50 years, you know? And he's like, well, and I loved your mom. I'm like, of course you loved mom. And he's like, you know, and Gene has been really amazing. and I went, wait, dad, are you about to tell me that you're dating Gene?

56:50And he was like, well, yeah. I mean, how would you feel about that? And I was like, oh my God, dad. Yeah, what am I, five? Yeah, that's fine. Okay, good. Like you're in your eighties. Like gather your rosebuds while you may. Like don't worry about, of course. Yeah, Jesus, I thought something was wrong. Like I thought you were sick or something. I thought you were depressed. And he's like, well, no, I just didn't know how you'd feel about it. I'm like, dad, like Gene's love, like by the way, he's 80 something. him he needs somebody to take care of him he's of the generation he needed a woman to take care of him and she's of a generation where she needs a man to take care of so they're thrilled they've been married now for i don't know eight years something like that eight and a half years and she's lovely she's a lovely person she's a lovely woman but i hung up the phone with him and i called my sister who's a dentist and they said you know oh she's with a patient i said pull her out i need to talk to her so they pull out she's like what's the matter i said dad's dating gene she goes okay okay, who cares?

57:44I was like, nobody, but he's going to call you and scare the shit out of you. So I just want to tell you the ending. And she's like, oh, okay. Yeah, that's fine. Why should I care? I'm like, I have no idea. I think he thinks we're five. And so the truth is like, it really depends on where you're at in your life. You know, like if your children are teenagers, they might understand it differently than if you have a seven-year-old or a nine-year-old, that's a different thing there. Are you replacing me? Who's my mom and my dad? What do I call this person? where do they fit? Do they like dad or not like dad?

58:11Do they like mom, not like mom? Like, does this someone I'm allowed to tell you that I care about or no? Like it creates loyalty binds if you don't do it right.

58:19Randall Kaplan:For me as a dad, I live for my kids. We have a nine-year-old and a six years old. And the person that my wife chose to date while we were still living in the house together, but technically separated is a guy named Matt Harvey. For those people who don't know, Matt Harvey was a pitcher for the New York Mets and was a member of the California Angels baseball team and a very famous pitcher named Thomas Staggs died of a drug overdose suddenly. And according to the New York Times, he used drugs supplied by Matt Harvey the night of his death. Matt got immunity for testifying. They go after the bigger fish, which generally means if you talk to prosecution lawyers, you otherwise would have been charged with a crime.

59:00Randall Kaplan:The equipment manager serving 22 years in federal prison, and generally it's just not the kind of guy who I want her to date. My six-year-old tells me all the time, he's over too much and I don't like him. Our six-year-old tells the nanny that as well. And it's just, it's very, very frustrating for me as someone who loves my kids more than anybody. I don't think he's a good person. I've spoken to ex-girlfriends. I've seen texts. They're terrible. They don't have good things to say about them. And I'm worried about my kids. So what's your advice to people like me who are very frustrated, to just whatever I say to my ex-wife.

59:37Yeah, I mean, this is the kind of thing I see happen in divorce situations. I think most people would acknowledge that if this same behavior was happening in the opposite direction, that it would not be considered acceptable. So I think what it demonstrates, and I see it a lot, and again, it doesn't mean someone's a terrible person, is that people just are not keeping their children as the priority. Like it really is supposed to be about, like clients come to me all the time and they say, well, here's what I want in terms of visitation, or here's what I want to do with this holiday, or here's what I want to do with that.

1:00:13And I always say, do you understand? A judge's job is not to figure out what you want. A judge's job is to figure out what's good for your kids. So if I go in and I go, my client wants this, nobody fucking cares. Like my job is to go in and say, your honor, this is what would be good for the children. This is what would be right for the children. And by the way, it should always be about setting a standard that you would be willing to be held to. And I think that that's the rule set you have to apply is to say, I think that both of us should be thoughtful and careful about how we introduce new relationships with our children.

1:00:45Now, look, I will tell you, I know nothing about this person.

1:00:47Randall Kaplan:I was a Yankee fan more than Mets fan, so I have no idea who he is. I don't know your soon-to-be former spouse, so I don't know anything about your situation. And I'm sure that if I was speaking to her, I can tell you as someone who's been doing this job for a really long time, If I was speaking to her, she would tell me a very, very different story about your marriage. I guarantee it. People, I have been doing this job for over 25 years. And no one has ever come into my office and sat in that chair across from me for a consult and said, I would really like to screw up my entire life and my kids as much as possible.

1:01:20I'd like this to be as expensive and protracted as possible. I really want to just burn up any goodwill between me and my co-parent. and I'm going to make a lot of really irrational, awful decisions and let's do this thing. No one's ever said that. Everyone comes in and says the same thing. I want to be fair. I want to be fair. I want to be fair. The problem is their spouse is in a lawyer's office like mine across the avenue saying the exact same thing and their definitions of fair are completely different. So I guarantee if I talk to him, if I talk to her, I would hear a completely different story and I'm often reminded of the lyric of David Byrne from The Talking Heads, that facts all come with points of view and facts don't do what I want them to.

1:02:00Like the truth is, facts come with points of view. You just described for me your point of view about this person, the relationship, how it's been handled, why it's bad. Nothing you said is nonsensical to me.

1:02:13Randall Kaplan:Nothing you said did I go, well, if those things are true, you're wrong, okay? Nothing. Everything you said was very reasonable. I can almost guarantee if I talked to her or to him, they would probably say something that also made some level of sense or they would deny the veracity of some of the things that you just said and that's the thing about being a divorce lawyer for 25 plus years is you just listen to so many people's stories and do I eventually learn oh, oh, my client's the asshole. Yes, but it's rarely at the consult. It's sometimes six months into the litigation. I had this experience last week with a client I currently have that we're about to have a trial and I have been quite a few miles with this person and halfway through a conversation, I thought, oh, they're terrible.

1:03:10This person is terrible. Like this person, I'm representing the terrible person and this is going to be an ugly trial because this person, it does not stand up to scrutiny. And my job was to say to this person, you're not going to do well on the stand. Your logic doesn't stand up to scrutiny. I was just questioning you mildly and your whole logic folds up. So I would encourage anybody in your situation, her situation, his situation, to, you know, really steel man and straw man my worldview. Because what you start to realize is like, oh, okay, like my arguments aren't foolproof. my arguments aren't like it.

1:03:48Look at it very honestly about like, what is me and what is my subjective assessment of the situation? And what is objective factual truth? And again, as a lawyer, it doesn't matter what I know. It matters what I can prove.

1:03:59Randall Kaplan:The issue is, you know, I want to protect my kids, right? In this situation, I can't control who she dates. I have read hundreds of texts with various girlfriends that he sent and they say what they say. I would like to either in business or personal relationship, put myself in someone else's shoes and ask myself when I analyze situation, what would I do here? If I were dating somebody today who asked me to meet their kids after three months, I'd say no fucking way would I do that. It's not good for the kids. I would have better judgment. Now, if I were insecure and couldn't keep a relationship and were love bombing every girlfriend, which I understand Matt has done, I wouldn't do that.

1:04:39Randall Kaplan:And as one of my best friend said when he learned about matt you know his quote was um and he's he's the ceo of one of the biggest law firms in the country he's you know counsels billionaires like you and you know his his famous quote was what a dickhead and again like you don't want but you know there's a reason why you are divorcing this person and that is that you have very different ways of approaching the world i'd imagine and you have very different ways of relating to yourself so it's not really surprising to me when somebody says, well, I would never do that, or I would never approach this that way.

1:05:17Yeah, you're explaining why you're getting divorced. Like this is a person who does not relate to the world and engage the world the way that you would. And by the way, they choose romantic partners who don't engage the world the way that you do. There's a level of that that's pathological that you're describing, but there's a level of that that's also perfectly acceptable, like perfectly healthy. Like my ex-wife is remarried to a guy for 15 years. So longer, far longer than we were married. And he is nothing like me. Like he is, we have very different personalities. He is lovely. He is a lovely person.

1:05:55I like him very, very much, but we could not be more different. And if you met him and met me and went, a woman was married to both of these man, you'd go, wow, has she got like schizophrenia? Like that's crazy. Like, because they're so different. And he's right for her. I'm not. He's who you choose when you're in your late 20s or early 30s and you have a better sense of who you are. I'm who she chose when she was 19, you know, and vice versa. But again, does that mean we're bad people? No, we're different people. We're incompatible people. So yes, if your ex-wife or soon-to-be ex-wife was the kind of person who was as thoughtful and considerate as you are, or if the man she's dating was as thoughtful and considerate and child-oriented and child-centered as you are, would they do what you're doing?

1:06:50Yes. And if my grandma had balls, she'd be my grandpa. Like, that's not who this person is. So by the way, what's the remedy to that? Get divorced from them. You know, what's the remedy to that when it comes to your kids? There kind of isn't one, except to try to minimize the negative impact that has on your children, shield them from the loyalty binds that it creates. And eventually your children will get to an age where children inevitably do, because the thing about kids as they grow up, is get to an age where you can say to them,

1:07:26Randall Kaplan:hey, your mom and I are very different people. We live our lives in different ways. And when you decide how you're going to live your life, you'll look at mom's life and the fruits that it bore. You'll look at my life and the fruits that it bore. And then you'll become who you are, whoever you choose to be. And I will tell you, and I say this with love, and I don't know if you've had this experience because I know that you divorced your first wife and it was a relatively amicable split. Very amicable. Okay, and I the same. very am. But I will still say as amicable as it was, one of the most challenging things I experienced as a man was learning how to navigate the personality characteristics of my ex-wife that I didn't particularly like when they manifest in my sons.

1:08:11When my sons would lose their temper the way my ex-wife did. When my sons would say biting things the way my ex-wife would. I couldn't divorce them. They're my kids. I love them more than anything. I had to learn how to navigate that. And I imagine she had to do the same when they were impatient the way that I am. And when they were sarcastic the way that I can be, it must've been hard for her. It must've been hard for her to learn to navigate because the man she married now is very patient and not sarcastic. He's very sincere. He's a therapist. He's a good, good man. And I'm not saying I'm a bad man.

1:08:46We're just different, you know? But the truth is like, it must've burned her ass the same way it burned mine to have to love these boys and see the pieces of me that are in them. I know it burned me to see the pieces of them that are made up of her. But it also really, really was a growth opportunity for me. It also taught me that, Hey, you can't walk away from things. You can't like you, you, you have to walk away from some things, but some things you got to figure out how to navigate. You got to figure out how to navigate personality traits that you don't like in someone you love more than anything, you know?

1:09:22And that was a growth opportunity for me. And that has paid dividends in other relationships, my employees, my friends. So what I would say is what they say all the time in the recovery community, which is there's three things you can't change. You can't change the past, you can't change the truth, and you can't change another person. You know, you can't change your ex-wife and you can't change this person she's dating's behavior. You can ideally use the judicial system to create rules and things like that, because most people respond to fear or greed. Those are the only two things. Those are the only two real levers.

1:09:53You know, I've often quoted a Cormac McCarthy novel where he says there's two things that make a person change, God and pain. And not everyone believes in God. So sometimes your job is to create leverage and inflict pain that can be an educational kind of pain for a person. But what I would say without question is a lot of what you can do is change how you process that and how you experience it. And that's very hard for guys like you and I who are used to bending the world to our will and who see the world as a place where we can go in and paint it like a canvas and try to make something beautiful with it and try to like, we go, why not?

1:10:30Somebody else could do it. Why couldn't I do it? Let's do it. Let's try. That's how the entrepreneurial spirit works. That's how men of will make a beautiful world. It's hard when there's things you look at and you go, I can't do a lot about that.

1:10:42Randall Kaplan:I just have to, I have to ride it out. That's really hard, man. It's really hard. Yeah. And, and it's something Jim that I need to work on. I'm not, I'm not doing a very good job on it, but with my therapist as well, we're, we're working on it. Um, and, and I will, it's a hard thing to do. It's a hard thing to do. It's very hard. It's very hard. Cause I hear it from, but you're a man who can do hard things. You're a man who can do hard things. You've proven that in your life. And so I think the fact that you identify it as something you want to work on. And by the way, that's not to excuse. I mean, look, you know, when we all have things that we do that it's like, man, we could do better.

1:11:18And, you know, I don't believe that we should just turn our back when someone is doing something harmful to our children. I think that sometimes what I have to do is invoke judicial remedy for those kinds of transgressions because that's how it works. You know, like the only thing that stops a bad man is another bad man. So a lot of times my job is to come in and to bring the power of law to bear on a situation where someone is doing the wrong thing. But not every problem has a judicial solution. And that's a hard thing for people sometimes to realize and accept.

1:11:49Randall Kaplan:One thing that I want to say also, and I know you're happy that your ex got remarried. My first ex is getting remarried this month, later this month, as a great guy. Super happy for her. He's amazing to my kids and to her and makes me super happy. One thing that everyone wants to know, and I said this to Jim at the beginning of the show where I said I got a ton of DMs to have you on the show. You have a ton of women fans out there. My mom says he's so handsome. I love his tattoos. What's happening in your dating life? You're a very eligible bachelor. You're a good-looking guy. You're cool. You're fun.

1:12:36Randall Kaplan:You got the three-piece suit on. You have money. What's your dating life like as that kind of person, as a divorce lawyer who sees, like, everything about relationships? Are people afraid to date you? You know what I'll say is I have a lot more women interested in me than I ever did before. I think it was easier for me for many years before the media thing because I was just working so much that I didn't really interact with a lot of women except for the women that I work with and they've always been off limits. So it wasn't much of a thing. And now I have a lot of women sliding into my DMs and interested in me because they've got to know me through my media profile.

1:13:15What I'm learning very quickly from that is it's like reading a book I wrote or having a crush on your professor. Like you think that this person has a level of wisdom, but really like I just know a bunch about like a small list of things. You know what I mean? And people think there's something about that parasocial thing that people think they know you. And I think it creates in people a, there's an inequality in the relationship right from the beginning. Because like I meet someone on the street, if I meet a woman and she says, oh, I'm a big fan and I can tell there's a flirtation there. We're already at kind of an imbalanced state because she knows a lot about me and I know nothing about her.

1:13:58And so we're kind of at a different place, right? So I've been very blessed in my life that I've been in love more than once. And I've had a number of what I would consider to be very deep and fulfilling relationships with women. But do I consider a fulfilling romantic relationship at this stage in my life like a high priority goal? No, it's not a high priority goal. I have a mission and I enjoy what I do very, very much. And I think that relationships, this is a terrible metaphor, so I apologize for it in advance, but I don't know of a better one. When I was first deciding whether to get a dog or not, okay, this is many, many years ago, I was like relatively newly divorced and I was like, maybe I should get a dog because I really I love dogs.

1:14:45I did get a dog. My dogs are elderly now. They're 15 and 16. I love them. It's the best decision I've ever made. But if you say, you know, it's a warm, beautiful, sunny day, and I'd like to get a dog because we could go play in the park and play fetch. That's a great idea. Here's the problem. You have a dog. You got to have a dog all the time. So you better be prepared for when the dog eats something it wasn't supposed to and now like poops all over your floor. And you better be prepared for changing aspects of your life because the dog has needs and it's not wrong of the dog to have needs. Now, I'm not trying to compare women to dogs, although I love dogs so much that that actually would be quite a compliment.

1:15:22Randall Kaplan:I just think if you're not prepared to be in a relationship when it's hard, if you're not prepared to be in a relationship that you give it your full attention, and I don't mean your full attention 24 seven, but like you can give it predictable, reliable, stable attention. I don't think you have any business being in a relationship. So I think it's a question of like, where are you in your own journey and what's important to you? And you know, would it be lovely to have the companionship of someone to be on vacation with and to have fun with on a Saturday? Yes, of course. But do I like the fact that I can now get up and do whatever the fuck I want to right now?

1:16:04Like I can work for another five hours and fall asleep on the couch in my office, or I can go home, or I could get on a plane and go to Paris. Like, and I don't have to ask anybody and I don't have to take them into consideration in any way that the only people I have to really take into consideration are my adult children, which really require very little of me, my dogs, which unfortunately or fortunately require a lot of me, or my employees and my clients. Like, there's a freedom to them. So everything has a price. Like, I think that what I learned when I got divorced was when you're, there's no perfect life.

1:16:39When you're married, you have one set of problems, but you don't have another. When you're single, you have one set of problems and you don't have another. I believe that the set of problems that comes with a relationship at this chapter and stage is a bigger set of problems than the set of problems of not being in relationship. But I also am not and have never been someone who was a particularly prolific Lothario, like want to have shallow relationships where I'm just sleeping with people. That's not my personality. It's not my proclivity. I don't think that it's a good way to model yourself.

1:17:17And I don't think it's honest. I think most women that I've met, they're not really happy with just having lovers. I think that they want something deeper, even if at the start, they just want something like just tangential. I think ultimately they eventually want something more stable. So you shouldn't, you know, you shouldn't create conditions where people are going to be disappointed. So that would be the longest soliloquy I've ever given on my personal feeling towards dating. So congratulations. You got that one out of me.

1:17:42Randall Kaplan:We're at the end of our show. I was concluded with a game I call fill in the blank to excellence. These are generally one word, one sentence answers. Are you ready to start? The biggest lesson I've learned in my life is... To doing the right thing to do are almost always the same thing. My number one professional goal is? Just more of the same. More of the same. I'm having a blast. I don't have to prove anything anymore. I'm working on interesting cases. I'm making a lot of money and I love what I do. So just more of the same. My number one personal goal is? Find peace. Find peace in my heart.

1:18:14Randall Kaplan:My biggest fear is? Right now losing my dogs because they're elderly and I love them very deeply. and I have an issue with anticipatory grief. And so I've been bracing for the loss of them for a long time. I've loved them very deeply for the 16 and 15 years I've had them. And I know that I'm in the winter of their life and I know it's going to hurt. It's going to hurt when I lose them because I love them so much. But grief is the receipts for love. The craziest thing that's happened in my career is? That I was a C student at a state college in New Jersey working as a waiter in Pizza Hut. and somehow I'm the most well-known divorce lawyer in the entire world.

1:18:53Randall Kaplan:I love that. The funniest thing that's happened in my career is? The same exact answer as the prior one. That I was a C student at a state college and worked at Pizza Hut and somehow I'm the most well-known divorce lawyer and possibly the best known lawyer in the world. The best advice I've ever received is? Gosh, that's a hard one. I've received so much good advice from so many people. I think it'd be the same thing I said earlier, that the hard thing to do and the right thing to do are almost always the same thing. My mom was the one who said that to me. And it stayed with me as the truest of statements that the hard thing to do and the right thing to do are almost always the same thing.

1:19:30Randall Kaplan:I think I know what you're going to say to these. 10 years from now and 20 years from now, I'm going to be doing... 10 years from now, probably something very similar to what I'm doing right now. I'll probably still be doing this. I'll have written a couple more books because I have two of them coming out the next 12 months. One fiction and one nonfiction. 20 years from now, 20 years from now, I'll be retired. I'll be living in the woods. I have 33 acres in the Catskills in the middle of the woods. And I'll probably be up there a lot more. And I'll probably have a bunch of animals that I live with.

1:20:06And I'll do a lot of cooking and I'll do a lot of reading. I'll probably still be doing some writing. That's probably what I'll be doing in 20 years. I won't be practicing law anymore in 20 years. I don't see myself, this is a game you got to play hard. And I don't see myself pushing it red line the way I do now.

1:20:27Randall Kaplan:If you could pick one trait that would lead to somebody's success, what would it be? Yeah, organization. I think extreme organization. I think being very focused and organized is really, really important. The most important thing that's contributed to my own success is? The people I love. The people I've had the privilege of being able to love. and who motivated me to want to do things. I think if you have a why, you can endure anyhow. And I was very lucky to have people that I love and that were counting on me. And it brought out the best in me. The one thing I've dreamed about doing for a long time, but haven't is...

1:21:02Getting my black belt in Brazilian Jiu-Jitsu. I've been training it for 20 years and I've been a brown belt for seven of them. But I just, I haven't been consistently training at one academy for long enough to get my black belt from a professor. So that's something I, really plan to do within the next several years.

1:21:18Randall Kaplan:If you could go back in time and give one piece of advice to your 21-year-old self, it would be? Have lunch with your mom more often. You shouldn't be too busy to make a little bit of time while she's still there because she won't be there forever. If you could meet one person in the world who's alive today, who would it be? It would be me. I don't know. I wouldn't want to be anybody but me. I love my life. I'm so blessed. I feel so lucky. I'm playing with the house's money. I've done more, seen more, loved more, accomplished more. I'm so grateful for my life. I wouldn't want to be anybody other than me.

1:21:54Randall Kaplan:If you were the president of the United States today, the first thing you would do is? Quit. Forget it. I hate politics. It's the systematic organization of human hatred. I would have no desire to do that. I would have no desire to be president. If I had to be, I would issue an executive order that at the age of 18, you have to volunteer or as a hospice volunteer for at least six months. If your mom were alive today, what's the first thing you would say to her? I love you and I miss you. If you were in your deathbed, surrounded by your two sons, and you had 60 seconds to live, what's the one thing you would say to them that you want them to take for the rest of their lives forever?

1:22:32Yeah, I would just tell them that I love them. I think I've already shared the wisdom I have to give them. I would just tell them I love them and that I'll always be there. I'm in them now. You know, I think we're eternal. I'm not worried about it that we find each other like we all I think we all become stardust again

1:22:49Randall Kaplan:the one question you wish I had asked you but didn't is how did I get so damn handsome no uh yeah I don't know I don't know you covered a lot of ground I have to tell you I don't this has been one of the most if not the most comprehensive interview I've ever done your extreme preparation is like shocking to be on the other side of because I've now done hundreds of interviews with some of the most A-list podcasts in the world. And a lot of them, I get the impression they have no idea who I am. And they've definitely not read my book. And they asked me a lot of overly simplistic questions. And you were just armed with a history of my life that was, you know, I've seen your other interviews, so I wasn't surprised.

1:23:29But it's surprising to be on the other side of it. Because I actually was talking to my assistant during our short break. And I said like, oh, man, I feel like I can call my therapist and just cancel tomorrow morning's appointment because I've already had it here. Like I've already like got into anticipatory grief and the loss of my mother and the interplay between my father's alcoholism and my mother's, you know, potentially impending death. And so, yeah, I think, um, I think you've covered it all. I think you've covered the whole thing. I'm very impressed.

1:23:57Randall Kaplan:Well, that's very kind of you. I appreciate that. Um, are there any questions you want to ask me before we finish today? Were you always this curious? I mean, are you that kind of person? Have you always been this curious? Because you go deep. I mean, not just in this interview, but I've seen you go very deep in your conversation with Gary Vee, in your conversation with Tony Robbins. You know, like some of these conversations I've seen you do, you go very deep and I assume that it's a function of your own curiosity. Like, were you born curious or is it something you've deliberately cultivated?

1:24:29Randall Kaplan:No, I was born curious and I love meeting people and I love learning about what motivates people. So I don't want to repeat questions that the other podcasters have done. And by the way, I started my podcast five and a half years ago. I've never listened to another podcast in my life, and I'm never going to either. I'll do the research and the transcripts. I want to do things my own way. I always, I have an independent way and a creative way of thinking. And so I like getting to the bottom of things, not just the surface level. so I am curious I mean the goal of the show is to inspire motivate people and I don't want to just tell the stories I want to get 10 layers underneath because it really those are the stories the steak and al reference for example people don't like doing the shit work right I was a waiter and I get it and those are the questions that I want to be curious you've never been asked before and I am curious I'm curious to know how the world works how what motivates people and I love learning new things.

1:25:26Randall Kaplan:I'm omnivorous for knowledge, and I always have been. And I'm grateful my show has done really well, thanks to amazing guests like you. I've wanted you on my show. I got to tell you, a year ago, I didn't know who you were. And I can't tell you how many proactive requests I have, have had to have you on my show. And like I said, Jimmy, you give great advice. and I'm a huge fan. I'm grateful. This is the longest podcast I've ever done. We're going to make it free. You know, usually, you know, one of the things when you prepare is your guests always go longer, right? And it's part of the preparation.

1:26:06Randall Kaplan:People respect you right out of the gate. They know you've done the work. They want to reciprocate. That's why it's successful in business. That's what I coach. That's what I teach. This has been incredible. I don't think we had a dull moment. We'll be going at it now. Five hours. uh total maybe maybe longer so we're going to make this into three three episodes i mean you you've given i think i lost track over a hundred piece of advice that is very valuable that people are going to love and respect hopefully you're going to change lives i know i've learned a lot of things from you um on this show and again i've watched every clip you've ever done.

1:26:44Randall Kaplan:I've watched them all, hundreds, as part of my prep. And it really, you've made me a better person, more knowledgeable. And I just want to thank you for the incredible amount of time you've given me. I'm so grateful. I know, you know, you could have been making lots of money with clients and I think you're going to change the lives of tens of thousands of people for what you've done today. So I'm grateful. And a shout out to Lewis Howes. Lewis Howes called you and I said, hey, you know i i i texted you i got your number i have the service i texted you i got your number through this service your cell number didn't hear back from you dm'd you didn't hear back i'm like hey lewis who is the guest on my show we become good friends which is one of the great things about my show i've gotten to know a lot of my guests they come over from pickleball i love to host you when you come to los angeles love to love to i'm out there a lot yeah i mean it's been great so shout out to lewis i love you i thank you this is the best this is the best thank you so much it was a pleasure it really was and i have to tell you i i can always i can count on one hand how many podcasts at the end of it i feel i had this conversation with jay shetty when i finished my episode with him as i said to him because we went for like three hours three and a half hours so even less than this and i said to him at the end of it i feel invigorated i don't feel tired like i feel like oh my god i'm like ready to you know and i always said like to me that's the sign that it was like magic.

1:28:08Like that was a conversation worth having where I feel invigorated. I feel I learned something from the interaction and I feel excited at the end of it as opposed to drained and tired. And so this is one of those. So you're on one, you're in the one hand club here. So I, I really appreciate it. I'm really glad. And I hope it was a value.

1:28:25Randall Kaplan:Yeah. Huge value. You know, when we took a break for lunch, I went home and I had tons of DMs, like 25 DMs. How'd it go, Jim? How'd it go, Jim? I said, man, we're going like, we're halfway. He wants to go. I'll be out. I'll be out in LA within a couple of months. And when I do, we'll have to meet in person. I'd really look forward to it. Okay. Look forward to it. Good. Good stuff. Thank you, brother. You as well, man. You as well. Talk to you again. Take care, brother. Bye now. Be good. Bye-bye. You're listening to part three of my incredible interview with Jim Sexton, the most famous divorce attorney in the world, and maybe the most famous attorney in the world in general.

1:28:57Randall Kaplan:It has been an incredible interview, my longest interview in five and a half years doing my show. If you haven't yet listened to part one and part two, be sure to check that one out first. Now without further ado, here's my incredible interview with Jim.

From the publisher

What if an affair isn't where a marriage first breaks, but the moment years of disconnection finally become impossible to ignore?

After more than 25 years and 1,000 matrimonial cases, renowned divorce lawyer Jim Sexton reveals the five types of infidelity, the warning signs couples routinely miss and the painful question betrayed partners almost never ask.

In Part 3 of this extraordinary conversation with Randall Kaplan, Jim begins with one of the most shocking prenuptial agreements he has ever encountered: a clause that reduced a wife's alimony by $50,000 for every ten pounds she gained. The judge called the provision disgusting, but upheld it.

Jim then explains how marriages can slowly unravel when couples stop doing the seemingly insignificant things that once made their partners feel noticed, desired and loved. Neither person may recognize the damage while it is happening. By the time an affair occurs, it may be the final symptom of a relationship that has been deteriorating for years.

Randall and Jim explore:
• The five distinct types of infidelity
• When flirting crosses the line into cheating
• Why revenge affairs create more pain instead of relief
• Whether sex addiction can become an excuse for avoiding deeper problems
• The questions men and women commonly ask after discovering an affair
• Why learning every sexual detail may make healing more difficult
• The conversation couples should have before resentment becomes betrayal
• Whether trust and intimacy can be rebuilt after infidelity
• Why opening a struggling marriage is often treated as a final Hail Mary
• When divorced parents should introduce a new partner to their children
• How to protect children from loyalty conflicts after divorce
• Why preparation and organization have been essential to Jim's success

Jim also opens up about his own dating life, the freedom and responsibilities of being single, his relationship with his sons and the grief of knowing that the people and animals we love will not be with us forever.

The conversation closes with Jim's deeply personal reflections on love, success and mortality, including the one message he would leave his sons if he had only 60 seconds to live.

Jim also tells Randall that this was one of the most comprehensive interviews he has ever done and calls Randall's Extreme Preparation "shocking to be on the other side of."
What causes more damage to a marriage: the act of cheating or the years of disconnection that often precede it?

Share your answer in the comments. If this conversation made you reconsider love, loyalty or marriage, please like the video, subscribe to In Search of Excellence and share this episode with someone who needs to hear it.

Timestamps
00:00  Getting caught cheating versus confessing
00:28  Who should never get married?
01:55  The disgusting prenup clause a judge upheld
07:03  How small acts of neglect can predict a divorce
11:44  When does flirting become cheating?
16:43  Jim Sexton's five types of infidelity
25:10  Is sex addiction real or sometimes an excuse?
27:14  Can someone cheat and still have a happy marriage?
33:50  What betrayed partners ask after an affair
39:04  The painful question almost nobody asks
43:10  Do open marriages work?
47:43  Why preparation is the foundation of Jim's success
51:20  When should children meet a new partner?
57:31  Protecting children during and after divorce
1:03:21  Accepting what you cannot control
1:11:11  Jim's honest answer about his dating life
1:17:04  Jim plays Fill in the Blank to Excellence
1:21:43  Jim's final message to his sons
1:22:11  Why Jim called this one of his most comprehensive interviews


About Jim Sexton
James J. Sexton is a leading matrimonial and family law attorney who has handled more than 1,000 cases during over 25 years in practice. He is the bestselling author of If You're in My Office, It's Already Too Late and How to Stay in Love. His candid insights into marriage, divorce, infidelity and relationships have made him one of the world's most widely watched legal voices.

Connect with Jim Sexton
Website: https://www.nycdivorces.com/
Instagram: https://www.instagram.com/nycdivorcelawyer
YouTube: https://www.youtube.com/@sextonshow
TikTok: https://www.tiktok.com/@nycdivorce

Watch Parts 1 and 2
Part 1: https://www.youtube.com/watch?v=_qKNSync_uw
Part 2: https://www.youtube.com/watch?v=NrHjXLgBUVo

Listen to In Search of Excellence
Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310
Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6L
All episodes: https://www.insearchofexcellence.com/

Work One on One with Randall Kaplan
Randall privately coaches a limited number of entrepreneurs, executives and high achievers who want to accelerate their personal and professional success.

Apply here: https://www.randallkaplan.com/

Extreme Preparation TEDx Talk: https://www.youtube.com/watch?v=MIvlFpoLfgs

About Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.


Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X

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