In short
How modern dating advice (types, “spark,” red flags, never settling, protecting peace, endless options) can undermine real relationship skills; why chemistry fades and “quiet qualities” and commitment matter more; dating apps increase fantasy, pickiness, and avoidance; relationships improve through discomfort, communication, accountability, and “doing the work.”
Guest backgrounds
Amy Chan is a relationship expert who studies dating through psychology and neuroscience. She founded Renew Breakup Bootcamp and authored Unsingle. She built her approach after a painful two-year relationship ending in betrayal, followed by 2.5 years of healing and forgiveness; she then created a curriculum by bringing in experts (e.g., CBT, somatic therapy).
Key claims
Meet “good enough” people and practice love; instant chemistry isn’t predictive; ghosting/avoidance often reflect conflict-avoidance patterns; arranged marriages can last longer due to commitment and fewer “refund” options; situationships carry hidden heartbreak risk; attachment is a spectrum; discomfort is normal and learnable.
Notable examples
swiping/“ick” judgments on apps; coffee-date as a low-pressure “vibe check”; a friend’s “does this story serve you?” forgiveness turning point; buyer’s remorse reframed as “range of emotions” in art.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Secrets to Great Relationships
0:00 to 2:04
Learn how successful couples work on their relationships and the importance of effort.
“When I look at my favorite couples, and I have a few of them, like the couples that I like, I want a relationship exactly like theirs.”
Amy Chan's Accidental Career
2:27 to 3:08
Discover how Amy Chan transitioned from personal struggles to becoming a relationship expert.
“And I think you and I are very similar that this was not our chosen path.”
Finding Purpose After Heartbreak
3:08 to 6:40
Understand how Amy turned her heartbreak into a mission to help others heal.
“So I was in a relationship in Vancouver and I thought I was living the dream.”
The Importance of Friendships
6:40 to 9:40
Learn about the value of friendships in our lives and their impact on dating.
“doing that I was like this isn't helping it's like it all came together like glue and it just hit and I just didn't have any resentment for him after that.”
Challenges of Modern Dating
9:40 to 11:35
Explore how dating apps and societal pressures complicate modern relationships.
“which probably makes me more dateable anyway.”
Navigating First Dates
11:35 to 14:00
Gain insights into making the most out of first dates and evaluating connections.
“I think it can be done, but I think that there are certain set of skills we need to learn for dating.”
Navigating Early Dating Dynamics
14:00 to 15:00
Learn how to approach the early stages of dating without overwhelming pressure.
“I call it the evaluation stage where you get to know someone and you see like, is there an alignment of values?”
Understanding Ghosting and Conflict Avoidance
15:00 to 16:40
Explore the reasons behind ghosting and how conflict avoidance impacts relationships.
“Like, they don't know the rules of engagement anymore.”
The Spectrum of Attachment Styles
16:40 to 18:20
Discover how attachment styles affect dating behaviors and relationship dynamics.
“And then they're, they're not constantly at you for more energy, more time that will probably make you, your nervous system ease in and want them a bit more.”
Communication and Avoidance in Relationships
18:20 to 21:19
Learn the importance of communication when dealing with avoidant tendencies.
“She's on vacation and she's sending me everything she's doing.”
Show all 22 chapters
Situationships and Modern Dating
21:24 to 23:20
Examine the rise of situationships and their impact on commitment.
“Too many people think the way to build a career is to keep getting better at what you're already doing.”
The Importance of Discomfort in Relationships
23:20 to 26:10
Understand how discomfort can lead to growth and commitment in relationships.
“Before, if you met through colleagues or a family, like there's social consequences if you don't behave properly.”
The Value of Effort in Relationships
26:10 to 28:00
Learn why commitment and effort are essential for successful long-term relationships.
“like what do you mean I have to do work?”
The Mindset Behind Arranged Marriages
28:00 to 29:10
Explore how commitment and mindset differences impact divorce rates in marriages.
“and I don't think that a lot of people have that mindset.”
Understanding Situationships
29:10 to 30:32
Discuss the dynamics and emotional consequences of being in a situationship.
“And so if the vibe isn't vibing, I'm out.”
The Concept of Leaky Energy
30:32 to 33:19
Learn about the idea of leaky energy in relationships and its implications.
“And in my experience, they were girlfriends.”
Emotionally Corrective Experiences in Relationships
33:19 to 38:11
Discover how safe relationships provide opportunities for healing and growth.
“You're just getting that validation from a lot of people and you're not even aware of it.”
Changing Our Dating Mindset
38:11 to 42:03
Explore methods to shift dating perspectives and expectations for better outcomes.
“What's frustrating about this conversation is it seems like why can't we learn these damn lessons?”
Understanding Attraction and Relationship Patterns
42:03 to 45:00
Learn how familiarity influences dating choices and the importance of recognizing dating patterns.
“I know why a lot of my relationships for many years failed.”
The Impact of Social Skills on Dating
45:00 to 46:39
Explore how social skills have declined among young people and the anxiety surrounding dating.
“And so the idea of going out in the wild at a coffee shop and approaching someone and risking rejection or someone not interested in you, there's so much anxiety of doing that.”
Embracing Discomfort in Relationships
46:39 to 48:35
Discover why learning to embrace discomfort is crucial for dating success and emotional growth.
“I think the thing that I've learned as I've grown older, which is I saw negative feelings, bad feelings as somehow making me weaker.”
Reframing Relationship Narratives
48:35 to 49:31
Understand the importance of the narratives we create about ourselves in dating and relationships.
“You go and you approach someone at the coffee shop or you DM and you get rejected.”
Transcript
Automatic transcript. May contain errors.0:00Simon Sinek:When I look at my favorite couples, and I have a few of them, like the couples that I like, I want a relationship exactly like theirs. Like, my God. If I ask any of them, what's your secret? They all say the same thing, which is we do the work. You know? I think what you've explained when you talk about the friends that you have that have great relationships and the ups and downs and the working through it, you describe a great relationship. And I think a challenge that people have today is this mindset that they need to meet the perfect person first, and then it'll be great. We need to meet people who are good enough, and then we jump in with two feet.
0:39And then through going through the stuff, it's the hard stuff when you're there for each other, that it goes from good to great.
0:48Simon Sinek:Some of the dating advice that we follow might actually be making us worse at dating. Know your type, trust the spark, watch for red flags, never settle, protect your peace. And if someone isn't quite right, there are hundreds of other options waiting on an app. The problem is, the person who's great on a first date isn't necessarily great at a relationship. Instant chemistry isn't a good sign. A red flag might just be an imperfection. And keeping our options open can make us pretty terrible at actually choosing someone. That's why I wanted to talk to Amy Chan. For nearly two decades, she looks at dating through a sort of psychology and neuroscience lens.
1:29Simon Sinek:Why we're attracted to certain people and why relationships fall apart. She's also the founder of Renew Breakup Bootcamp and the author of Unsingle. Her work makes the case that finding love isn't just about finding the right person. It's about getting better at the skills love requires. It turns out dating takes practice. And so does staying in love. If you like what you hear, please remember to subscribe. This is a bit of optimism.
2:04Simon Sinek:This episode is proudly brought to you by SAP. Building trusting relationships with clients, it turns out, takes more than simply being an expert in your client's business. It actually is about empathy and being willing to step outside your own comfort zone. To learn more about SAP, the AI cloud ERP for businesses of all size, head to sap.com slash grow. I'm always fascinated about people's careers and how we stumble into them. And I think you and I are very similar that this was not our chosen path. No. I never imagined I'd be doing what I'm doing. I don't think you imagined that you'd be an old relationship expert.
2:39Simon Sinek:No. You didn't come from this world. No. You didn't study it. and for so many of us who stumble into these things, it's our personal experiences that sort of, you know, the solutions we find to the struggles that we're finding. And so you started not by talking about how to people, you started by not trying to help people have relationships, but how to end them, right? Tell me about what happened to you that unleashed or opened up an entirely new career, your accidental career. Yeah. So I was in a relationship in Vancouver and I thought I was living the dream. And back then living the dream meant you date to get married and then you have children.
3:19And then the plan I had with this guy who ran a business was I would write on the side for fun and we would have kids and everything was set. And then a series of things happened. I lost my job. I moved in with him and then he cheated on me with a former co-worker of mine and it wasn't just a relationship that fell apart so much of my identity and future was wrapped up in that relationship like I am the girlfriend I'm the wife I'm the mother I was yeah the perfect girlfriend training to be the perfect CEO's wife like that's what I thought was my dream and that shattered and I shattered I it was dark Like it was so hard.
4:03And as an achiever, like there was nothing I could do to get out of that pain.
4:07Simon Sinek:How long were you guys together? Two years. Okay. Yeah. So I just, I really struggled. And when I came out of that, which took quite a long time, like two and a half years, I was like, what happens to those people who don't have friends that will lend them a couch or know what books to read or have a therapist? So I was like, I have to create what didn't exist for me. So that's what I did. And what were the things that you found for you that helped you get out of this malaise for, I mean, two and a half years to be stuck in mourning is a long time for any kind of loss. For sure. In relationship or otherwise.
4:47Yeah. And look, the intensity of the pain, I think, lasted six months. That's when it's like constant rumination, revenge plotting. But, you know, after that, like...
4:58Simon Sinek:You didn't do anything, did you? I didn't, but I had some really good plans. I want to know one of them. I want to know one of them. Buying bed bugs off the black market and infiltrating her home and his home. Wow. Wild, right? It was bad. But looking back now, you can recognize that if you did that, you're the crazy one, right? Yeah. Thank God I didn't do it. Oh, my God.
5:31Simon Sinek:okay this i'm fully aware that you know this episode we're going to be giving advice this is not the advice part don't do it we will not be giving instructions on how to get on the dark web or any links for bed bugs yeah so i mean like and after a period of time like that intense pain went away but i was resentful and like i was trying to date but i had a closed heart and any person I could rally into my corner about what a victim I was and what a villain he was that would be the story and it really wasn't until like two and a half years later I'm having coffee with a friend catching him up and I'm like telling him the story I'm like what this guy did to me and he just stopped me and he's like so Amy does this story serve you and I'm like no he's like oh can you was there any time when he did love you and he was kind and I just thought about it I'm like yeah there was this and that and I just realized in that moment for the last two and a half years like all I could see was a dark because that's all I was looking for and I went home that day and I wrote him a letter of forgiveness of how I grew and it was like all those things I was doing that I was like this isn't helping it's like it all came together like glue and it just hit and I just didn't have any resentment for him after that.
6:53Simon Sinek:What was the impetus for you to, so you found tools that helped you, that started with your friend sort of telling you that it doesn't serve you, this story, and then set you on a journey of healing and moving forwards and looking out the front window. Were you starting to dispense sort of armchair advice to your friends that was working? Did your story help others? Like, how did you go from healing yourself to giving away what you had learned? Yeah, I looked at everything that I tried and what worked and what didn't. And from there, I was like, okay, these things really worked. I was a writer.
7:37I've been writing about relationships for 20 years. So I would write about it in blogs, in different columns. and then when I had this idea I brought the best experts in that specific thing so if it was cognitive behavioral therapy I found an expert in that somatic therapy and I just learned from them and I created the curriculum yeah and that's how I started it started with like seven people half
8:04Simon Sinek:of them were my friends I love that I mean that's my story too yeah no I started giving talks in people's living rooms with their friend yeah yeah that's the same same same the i found you on the internet i saw you on on instagram okay and i was like so this is the best thing about having a podcast right which is if i see somebody on instagram who i think is really really cool and i was like hmm i could this would help me you know i get to invite them on the podcast have a conversation yeah it's about you but really it's about me we were talking before we turn on the cameras about my relationships and I probably fit many of the patterns um I I do think that there is a lot of judgment we put on ourselves society puts on us an expectation for example there's a lot of pressure that whether it comes from our families ourselves society whatever it is you know to have to have get married have the kids white picket fence I mean the the fantasy you had right I'm writing a lot about friendship these days because I think that we our society has over emphasized the romantic relationship and under-emphasized the friendship, the platonic relationship.
9:13Simon Sinek:And I have romantic friendships. Now, that doesn't mean that they're sexual. They're not. But they're deeply intimate. Yep. And there's love and there's care. Neither of us want to date each other. But they're very fulfilling. And it's kind of like you looking for the darkness, which is if I ignore all the goodness that I have in my friendships, I will feel lonely that I'm not in a relationship. But if I appreciate the friendships, it takes the pressure off, which probably makes me more dateable anyway. If there's just a lack of, got to get into this. Do you think that dating seems to be more difficult these days?
9:52Simon Sinek:I know young people are later to have sex. Young people are, the tenure of relationship seems to be shorter. What is the reason? what you've met a lot of people of all ages yeah can you discern that it's a young person challenge or is it a current day challenge like why does dating feel more difficult than it used to and it's too easy to simply say the internet right yeah uh i think dating apps have changed the way that we meet people but they change the way we think about people and if you think about the act of just swiping a hundred times a day that's what i used to do just swipe swipe swipe and the hundred person person I would look at like it's just there's so much incoming shopping and we know through research that the things that you're being so picky on for a dating app height looks hair whatever it is if you met that person at a dinner party you wouldn't have that same judgment but we're meeting people in these ways and it's changing the way that we see people so we can even go on a date, have a good date.
10:56The second date we noticed they wore flip-flops. And suddenly if you remember all the stuff you're being fed on Instagram, what an ick. Or maybe they asked you for coffee and not a dinner. And that advice is being told to you that a coffee, what a waste of your time. So I think that we are walking around with barriers around our heart. We don't trust the media. We don't trust our government. We don't trust thy neighbor. We don't trust anyone. And so how can we connect and see another person as a human being with flaws and have empathy when they mess up when we are doing that?
11:31Simon Sinek:And can that be done with internet dating? I think it can be done, but I think that there are certain set of skills we need to learn for dating. And there are a separate set of skills you need to learn to sustain a relationship. And there are people who are great at dating. They're charismatic. They know what to say. they're adventurous but those people aren't necessarily good at being a partner i in my experience what i found fascinating about online dating and i've done it and i've had success with it yeah um i've also made a lot of friends um but what i found really interesting is pre you know if you if you meet somebody offline whether it's at a dinner party or a museum or wherever it is the initial connection, there's charm and there's chemistry and the sense of humor.
12:25Simon Sinek:And it's after you make the connection, you say to the person, can I have your number? And then you go on the first date. But there's already a connection before the first date. Right. In online dating, the only thing you have is a picture, maybe some stats. Yeah. But usually not even that. Yeah. I guess where I'm getting at is it seems like online dating we're dating things in our imagination we're holding people up to standards in our imagination right and we're getting advice as you said you know people are doing it for clicks and likes but they're dispensing nonsense very often right i'm i'm so curious if this is it's clearly not a new experience but is it exaggerated have you noticed i want to know the frustrations you hear from people why their relationships aren't working yeah i mean like i think in your case i i would imagine for you people are probably pedestaling you and they have an idea of who you are before they meet you so meeting people online um they're not they already have like almost like a fantasy version i always advise my clients don't look them up because you're either going to pedestal them or you're going to judge them yeah so i mean don't do that if you can um but i think there's a lot of other frustrations and i think they there's different ones I hear from women and I hear from men.
13:43So I feel that the women are saying a lot of the times the guys are talking too much. And I try to explain to them that sometimes a guy is talking a lot. Maybe it's because they're narcissistic, but sometimes it's because they're nervous and they're trying to impress you. And I really advise people if you felt a connection of five out of 10, if you had a good time you go again i don't think the first date is meant to be like are they going to be my future baby daddy like stop that it makes you future too much pressure yeah it's just a vibe check and that is why coffee is totally okay which is which is like that charming interaction at a
14:23Simon Sinek:museum before you go the first date yes you have to treat this like the charming interaction exactly that's very good and then if that was good go again and then it's not until the third date to about 20. I call it the evaluation stage where you get to know someone and you see like, is there an alignment of values? Like those sorts of things. But there are things that you can only tell through experiences with that person. So I do think it's a great idea to go on that weekend trip. See how they handle stress when something doesn't work out. Meet their friends. Before you jump in and be in your mind of like, I'm committed to this person because they're so great.
14:56Or not. Yeah, allow that time. And I think for some of the guys, they're finding that they don't know. Like, do I kiss them? Do I don't? Like, they don't know the rules of engagement anymore. And there's a lot of ghosting going around. So, yeah, the behaviors are a little off.
15:19Simon Sinek:Ghosting is, I mean, like, if you go on one date and it doesn't work out, fine. Fine. Fine. But, I mean, I hear about six-month relationships where somebody just ghosts. For sure. It's a lack of ability to deal with conflict. And it is a reaction that they probably have had since childhood. I think that even with friends, like looking at these little data points of people who avoid problems, when there's an uncomfortable feeling, instead of having a conversation, they avoid it. That is very telling of how they're going to behave when a bigger thing happens. Okay. Is there a cure for avoidance?
15:57Simon Sinek:Asking for a friend. Yes, there actually is. So the newer research on attachment. Notice how my body language is completely closing up now. So there's newer research on attachment and that at any given time, you're on a spectrum of anxiety and avoidance. So before the idea was like you're in a bucket and that's just where you are. Which when I evaluate myself, it's of course complete madness. I'm a spectrum of things. changes depends on the person depends on how much sleep I got right I mean all kinds of things I can walk in and out yeah all the time so if you date someone who has a very full life right and like their idea of love is 50 of my love I get from my friends 50 I get from my romantic relationships which seems to be more of the world you are in versus a codependent relationship which is 100 of my love I get from my romantic partner that won't do well for you that will make you run for the hills, but someone who's got their own life going on.
16:55And then they're, they're not constantly at you for more energy, more time that will probably make you, your nervous system ease in and want them a bit more. Right. And so like what you want to do is like people who tend to have higher avoidance, they're really good in the first three months, right? Cause there's, you're intoxicated. There's the threat of like someone getting too close isn't there yet. And usually it's around the three month mark that something shifts. And what will happen is you'll find an imperfection. There's something that will make this relationship not viable for the long term.
17:30Is any of that resonating for your friend?
17:32Simon Sinek:Yeah. Yeah. Based on the conversations we've had, some of that is true. Right. Not all of it. Right. But some of it is true for sure. The experiment for a friend who does that is to challenge yourself knowing this is what's going to happen. and it's a very natural reaction where your nervous system is freezing and wanting to run because it doesn't feel safe. And you want to communicate like, hey, I'm feeling a little bit flooded and just try to have that conversation with that secure person and stick it out. Stick it out for another three months. Tolerate the discomfort and you will move through it if you are with a partner who is secure enough to deal with it.
18:13Simon Sinek:I did something recently for the first time in my life. so because i i the adhd doesn't help right right because with adhd i'll fixate on something i'll hyper focus and i'll give i'll accidentally love bomb somebody which can feel great yeah you know and so i'm responsible for giving a ton of energy and so when they reciprocate i'm like pressure but i'm they're just reciprocating my energy or the opposite happens with adhd which is i meet them i can't wait to and then i forget that i forget to call them two weeks will go by and be like shit you know but but what i did something recently for the first time ever which was lots of high energy really like each other going super well she starts reciprocating with tons of love and energy and attention i'm like absolutely not this is not going to work i you know i was like we've only known each other a few weeks and you're trying to lock me down and make me your husband i'm not ready for this but what i did was can i literally she was like texting me every day and sending me pictures.
19:11Simon Sinek:She's on vacation and she's sending me everything she's doing. I'm like, I've known you a week. You know, it's like, I don't need all this, you know? And so I called her up. I said, I have avoidant tendencies. I said to her. I said, and so when you give me all this attention, it's pushing me away. I said, you're not doing anything wrong. Yeah. I said, I said, I understand that I gave you tons of attention. I understand that you're matching my attention and my reaction is nothing to do with you. I just want you to know it's happening. And I want you to know that I'm going through this because I have these avoidant tendencies.
19:47Simon Sinek:And I simply just took full accountability, didn't blame her behavior, didn't make her wrong, and just took total ownership over my reaction to what was happening. And the fact that I played a part in creating the environment that would make it feel safe for her to love bomb me back. And it was great. Yeah, yeah. And I think what you did is super helpful because what typically people do when they feel that pressure is they avoid. And it's a very natural human reaction for someone to spiral when someone was giving you attention and suddenly it's like one word answers or now it's two days to reply.
20:28And in their spiraling, their natural reaction is to go run and get it. Right. So I have a lot of clients who spiral and they're like, I'm going to write this message. I'm like, please, for the love of God, send that to me. Do not send any communications while you're spiraling. And I get them to get into a calm place before they do any sort of communication. But it is, I think, letting someone know, even if you have more anxious tendencies, to be like, hey, just giving you a heads up. This is kind of what triggers me. I'm not saying this is your responsibility, but I just want you to understand.
21:02It's information.
21:03Simon Sinek:Yeah. It's information. Yeah.
21:09Simon Sinek:Instead of doing a straight ad read, we're pioneering something called an ad with authenticity. We want our ads to have valuable content for you, the listener. And this ad with authenticity is brought to you by SAP. Too many people think the way to build a career is to keep getting better at what you're already doing. SAP's David Robinson has learned that some of the most valuable growth happens when we go do the thing we've never done before. I came to SAP, I was in product engineering. I was brought in to work on a new strategy for the company relative to composite applications and the deconstruction of the ERP.
21:46Simon Sinek:Whatever that means. Whatever that means. I'll trust you that that's very important. It's super important and very exciting. I remember I was with someone at the time who said, you need to get out of that organization just for a period of time and rotate into a customer success function. You'll learn a lot. you'll learn about the mechanics of the business, how important it is to balance both product engineering with the successful sales and delivery. I said the hardest thing that you'll have to decide is if you're successful is going back. At the time I thought they don't know what they're talking about.
22:19Simon Sinek:Spot on. That's exactly what happened is that you never really go back and what's curious is that we almost, those that have been at the company a long time, we're almost a connective tissue that the customer appreciates. We did it differently in 1996 for this reason. You're the consistent. We're the consistent. Exactly. It's really, it's unexpected, but we're certainly a level of consistency, of predictability that a lot of customers have been longstanding customers have come to also trust and value.
22:59Simon Sinek:situationships. Yeah. Very popular. Yeah. Right. Are they a new situation or do we just have a name for them for the first time? I think we have a name for them for the first time. People have been casually hooking up for a long time. However, I think right now it's being amplified because the apps make it super easy. There are no social consequences, right? Before, if you met through colleagues or a family, like there's social consequences if you don't behave properly. but now that's out the window um and i think that people are less committing they're not committing as much it's really really hard especially for the younger generation to commit and then feel the uncomfortable emotions and those hard conversations and move through it why just stop it and find another person yeah and that's what they're doing because it's easy right again if you can shop for a new it used to be hard to meet a new person there was some risk with breaking up because you have to start again and how am I going to meet somebody?
23:59Simon Sinek:But now the shopping is so easy. In fact, very often people will start before they've broken up, see what the options are. For sure. So how much of what we're talking about, and I see it in work, you're seeing it in relationships, how much of it is simply people being uncomfortable with discomfort? And how much of the advice that you're dispensing is really people learning how to be uncomfortable, how to move through discomfort, how to manage discomfort, how to communicate discomfort. Yeah. How much of it is just that? Yeah, I mean, those are basic relational skills. But, you know, I just saw some research on how in Gen Z, their top value is self-care.
24:40And if you look on the internet, everything is about like self-care and like, you know, like your mantras and your matcha. Anything meaningful in life, building a career, a business from scratch, a loving, intimate relationship that goes through ups and downs where you're each other's rock. There's not, there's moments where there's no self-care at all. And for a season, you just have to like suck it up and be committed to the thing that you have, like that you're trying to build. And I think that is a muscle. And I think that is lacking in a younger generation. And that really does worry me. And so when people are wanting to get in a relationship, I think you also have to understand like, what is their definition of commitment and love?
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25:27Because if they're just about the feelings of being in love, that relationship is going to come to an head between 12 months to 18 months when the love chemicals take a nosedive.
25:38Simon Sinek:When I, when I look at my favorite couples and I have a few of them, I know who they are. Like the couples that I like, I want a relationship exactly like theirs. Like, my God. And it's not all unicorns and rainbows, you know, by any stretch of the imagination. But they have dynamics and they have levels of trust and they've protected each other's independence in ways that I find quite magical. If I ask any of them, what's your secret? They all say the same thing, which is we do the work, you know? And I think people forget that relationships are effort. Yeah. And that scares people. like what do you mean I have to do work?
26:15Simon Sinek:And what they're forgetting is that if you're on the receiving end of that effort, it feels really good when somebody's willing to do the work for me. And if it's mutual, oh my goodness, what a magical thing that somebody's willing to be uncomfortable, sit in discomfort, move through pain, not abandon, give second chances, give benefits of doubt. All of these things allow personal narratives not to take control of the relationship, fight to get to resolution, abandon ideas of who's right and who's wrong. All of these things, it feels incredible when somebody does it for us. And what I've learned about relationships and what has saved me and made me a better boyfriend is I no longer view relationships as what can I get from a person, but rather what can I give to this person.
27:10I think what you've explained when you talk about your the friends that you have that have great relationships and the ups and downs and the working through it, you describe a great relationship. And I think a challenge that people have today is this mindset that they need to meet the perfect person first and then it'll be great. It's like as if the perfect person is going to land on your lap on date two and you're like, oh, my gosh, like this is it. And that's just simply not the case. Like a great relationship is earned and it's earned through going up and down and seeing their flaws and that they leave their socks on the floor.
27:44And it's so annoying. But like you work through those things. We need to meet people who are good enough. And then we jump in with two feet and then through going through the stuff. It's a hard stuff when you're there for each other that it goes from good to great. and I don't think that a lot of people have that mindset.
28:08Simon Sinek:This explains your whole attitude, your whole point of view around dating explains why arranged marriages have a lower divorce rate than chosen marriages because they show up not because of the swipe but they show up knowing, okay, let the work begin. Is that, I mean, what is your theory as to why arranged marriages do better than chosen ones? Well, it's commitment And we know like through the paradox of choice, when you have so many choices or if you can refund something, you'll actually be less satisfied with the thing that you bought. And right now, like we don't have to get married anymore.
28:45Right. Like I think when we look at our parents age, there were a lot of things or institutions that kept a couple together or you're having family. We know now like it's not taboo to not have a family or to get married. You can go habitate. You cannot. And those things that would keep a relationship together, which will make you go through the uncomfortable times. And like, I have to abandon my own self-care during the season. We don't have that thing. So why are we together? Just for vibes? And so if the vibe isn't vibing, I'm out.
29:21Simon Sinek:So much of this is mindset, isn't it? I think it's mindset. And it's like... It's like your attitude towards... I think it is a maturity of looking at relationships and relationship skills. And, you know, I have I had a client, a friend yesterday who like wants to be my client. She's like, Amy, I really I'm ready to start dating. And she has in her head that like she needs to date a very, very wealthy person. And I was just trying to like go through like, do you really need that? And I was like, you're actually not ready. and the reason I know that is when someone is ready actually open for relationship what they tell me they look for in a partner is not those shiny qualities they're like they're they're looking at are they kind how do I feel when I'm with that person and when someone is just like they need to be this tall they need to be this age they I'm like you are operating from your ego and that is okay but this is not your season right now to get serious about a relationship because you actually don't want one.
30:25Because your behavior is contradicting what you say you want.
30:31Simon Sinek:Situationships. I want to go back to situationships. Okay. No, no, no. Because I think they're pervasive. And in my experience, they were girlfriends. We broke up and then never really broke up. Okay. We were no longer boyfriend-girlfriend. We technically could date whoever else we wanted. But we were just in this sort of limbo, nice space of spending a lot of time together, sleeping over, you know, these lovely situationships that were downgraded from the relationship we had, but never re-upgraded. Like, why are they, why are they bad or wrong when you have two consenting adults? They're not bad or wrong.
31:10However, typically what happens is one person wants more. So, and usually they don't know that until the other person finds someone else. Oh, got it.
31:20Simon Sinek:Because the situationship is safe. It has all the trappings of relationship. It has the guise of security until one person finds someone else to date. And all of a sudden you realize, oh my God, I've just been broken up with. Right. And then you're dealing with a breakup all over again, right? Right, right. Because in your body, your body doesn't know that there was a breakup, right? Those neural pathways never had a chance to print away. And so I work with those clients. Because there was no breakup that happened. No. babe we're we're breaking up or somebody cheated it's like they they did nothing wrong in finding a partner a new partner you can't like so there's no transition period from this is romantically over and then we're coming back to it in a different form right your body they're like we've been together this whole time so when one person in that situation find someone else you're just breaking up like it's square one and and there is nothing wrong with it but you have to also understand like if you are doing that and you say you want a relationship say you want a family you want to get married or whatever that is um is your heart actually open or is that real estate being taken up and we justify oh no it's totally fine yeah yeah so so what we're saying is they're not inherently wrong or bad but they do come with risk they do they come with risk of heartbreak if the other person actually does choose to find somebody you could sit in the perpetual situation or Or, to your point, that if I truly want a committed relationship, then I have to speak up about it because this isn't it.
32:51Simon Sinek:And my real estate and my heart is being taken up. In other words, I'll never find the thing I'm looking for because it's leaky energy, which is a term I just learned. Oh, yeah. Leaky energy. Yeah. I kind of like it. Yeah. I don't like it and I kind of don't like it. I like it when I'm talking about other people. What is leaky energy? There's two definitions of it. So one leaky energy is when you are just, maybe you're in a relationship, but you're super flirtatious with this person or you're liking people's Instagrams. There's like little micro cheating. You're just getting that validation from a lot of people and you're not even aware of it.
33:28And there's like a trail of people in your dust of like, is this person into me or are they not? And that does have an impact into your primary relationship, even if you think you're being innocent. um so that's the definition i operate on for leaky energy it's just being aware of how your energy is coming out and the root of your energy on like you could compliment someone but is that root of that compliment to like get validation and to start having some back and forth or is
33:57Simon Sinek:that really like a generous compliment i i want to unpack this more because there's nothing wrong especially if you're in a long-term relationship with finding other people attractive for sure looking down the street like oh she's cute and you know your girlfriend goes oh yeah she is cute you know like there's there's nothing wrong with that you know there's no intention yeah behind it and so if you're on instagram just swiping around and you know your doom scroll and you you like something for no reason and you click like and you keep scrolling and if it's you know some girl in a bikini and you click like or some you know whatever it is that you're into and you click like is that leaky energy so i think it depends because i have clients who are like upset that their boyfriend is like liking a bunch of Instagram models.
34:38Right. So if that guy is liking all these Instagram models, because there is deep down an intention of like, maybe they'll open up a conversation or DM that is micro cheating. Right. If that is like, Oh cool. Like I like her yoga pants, whatever it is. And it's genuinely coming from a place of like, I'm not trying to micro cheat. That's different. Right. The same action.
35:00Simon Sinek:How can you tell the difference? I think you have to look within yourself. You only, you know. Okay. Let's change tacks here. Okay. Okay. Have you found love? I have. Yeah. And how long have you been dating? Seven years. Seven years. Yeah. And you didn't get married? No, we will one day. Yeah. So what changed in you that after two years you were gunning for the ring and after seven years you're chill? Uh, I feel very secure and safe in the relationship. And I feel like before when I dated people and I wanted the ring and the wedding, a lot of that was because I didn't feel secure and safe in the relationship.
35:38So I needed that to lock it down. And what about you is makes you a better girlfriend than you were? I am in a relationship where I have had emotionally corrective experiences because I feel very safe with my partner so even though I'm a relationship expert I've still had like all of these old patterns that kind of awoke once I got in a relationship because when I was single there's not a lot that can trigger you you're like oh a little bit of anxiety but it's when you're in a partnership. And I just remember like not even that long ago, we were at a cafe and he like gets on his phone and goes on his email and I flipped.
36:24I was so mad. And I gave him like the silent treatment for two days. And after I was like, oh, this isn't normal. I'm having a disproportionate reaction to the offense. And I had to look in and I'm like, oh wait, this was because when I was like in kindergarten, my like my mom and dad would like forget to come get me. I would be waiting for 45 minutes and my time was never seen as important. And so now old Amy, like this tiny thing triggers this big response. And I brought it up to my partner and we had a conversation and I apologized for how I used to also react, which was pout and cry. And so like now I'm aware of that and I don't win all the time, but I can use my words and my silent treatment gets less and less.
37:16Simon Sinek:You used a term that I've never heard before, emotionally corrective experiences. Unpack that for me. Yeah, it's a term used in therapy a lot where it's in relation with another person where you can actually get triggered and it's an opportunity to almost course correct the old pattern or wound. And so now in a safer environment, You're now not just an eight-year-old adapting and trying to survive. You're with someone who you can trust. So the reaction to behave how you used to can come up, but you can talk to that person. That person isn't going to yell at you or ignore you. And you move through it and you're like, oh, it's actually okay.
38:00And the more you do that, that old wound that used to trigger an outsized reaction starts to get smaller and smaller. It's a process. It's a process that happens in relationship.
38:11Simon Sinek:And so that means both parties have to be open to the idea that you won't find the solutions after one infraction, but rather, as you said, the silent treatment gets shorter and shorter and shorter. What's frustrating about this conversation is it seems like why can't we learn these damn lessons? It's the same themes. It's, you know, it's learn to communicate. It's take accountability. It's, you know, learn how to sit in discomfort. Like none of this stuff is new. It goes back since, you know, the dominant relationships. you know why are we still having this conversation in you know 2026 i mean i learned how to dissect frogs when i was in school i didn't learn how to communicate or use non-violent communication to express my needs right um so the good news is now you dissect frogs all the time that's a valuable you don't need communication in your modern adult life you need to learn how to dissect frogs that makes perfect sense to me yeah what with all the talks people you're talking to what is one of your constant frustrations that no matter how much advice you give, no matter how much guidance you give, coaching you give, this problem just keeps rearing, like it's just a perpetual frustration for you in the advice that you give.
39:27I would say the amount people, of priority people put on instant chemistry and this thing that like, you're attracted to who you're attracted to and they can be drawn in by someone who has shiny qualities or fits their idea of a type. But we know that through hedonic adaptation, we adjust to those things. We adjust to their height. We adjust to their income. We adjust to, I don't know, their waist size. And that thing that drew us in that made us so excited, it goes away in like two years. So what's left after that? It's the quiet qualities. And research also confirms this. It's the quiet qualities that can predict if a relationship will be happy or successful.
40:15And it's how committed is your partner to you? How appreciated do you feel? How well do you handle conflict together? And that might not show up on a second date. And so I think there is, I'm very optimistic about love. I think that there are a lot of viable partners around us all the time. I think one of our main problems is we have blinders on because we are over emphasizing the things that don't matter in the long term.
40:44Simon Sinek:But it's easier said than done, right? I'm listening to you. I'm going, yep, yep, yep. But how do we change our mindset to not focus on those things, look past those things in a world that is bombarding us with those things. Yeah. I make my clients go on a dating experiment where they have to date nine different people totally outside of their type. Because if I tell someone, change your type. Logically, maybe go through one ear, go out the other. But if I'm like, okay, I have a client who has like a six foot height requirement. One of the people they have to date is someone shorter than them, right?
41:17I'll have a client who's like, I only date people 25 to 29. I'll have them date someone older than them. And the way they do this experiment is they can't get into a relationship with any of them. So it changes the way that they date because there isn't that pressure of finding the one. They're just like, I'm just doing this experiment. And at the end of the nine people, you can look at who was the best in terms of your benchmark, right? You can go back to that person or you now know in your future dates who you're looking, what type you're looking for.
41:46Simon Sinek:Is that communicated to these nine people? Because it's a little mean to go and... it's it's not communicated until it goes a little bit deeper and then someone will say something okay because it's a little bit mean to set up expectations like i'm on an experiment date but you're gonna fall in love with me well no but here's what happens right so a lot of the people who finish this end up getting in a relationship they don't finish it um and they say the exact same thing to me they're like amy i'm with someone i would have never given a chance to and it is human beings we're drawn to what's familiar so if you are familiar with the guy who's just a little bit unattainable um you're constantly going to be attracting and being drawn to that emotional experience so i'm the experiment makes you be in situations where oh like i'm now prioritizing kindness and other things i never did before and you get familiar with how that feels like.
42:40Simon Sinek:I know why a lot of my relationships for many years failed. I had a bad picker. I would date the wrong kind of person over and over and over again.
42:53Simon Sinek:And for various reasons. But I recognized that I had a bad picker. That they're good people, but they're not for me. And I'm not for them. But I kept finding myself dating very similar personality profiles over and over and over again. And it was a big deal for me to recognize that. And it's hard to break. It's very hard to break. I really like talking to you. Because I can't help but filter everything you're saying through my own experience, of course. And I'm soaking as much as I can.
43:28Simon Sinek:There's a... Maybe it's just because it's broadcast on Instagram and TikTok. But there seems to be more, skews younger, but I think that's just because they're broadcasting on Instagram and TikTok. All the people just aren't broadcasting their experiences as much. But there seems to be more people who don't know how to date. Forget about being in the relationship. There's one person that I follow on Instagram whose content I love. and she's super affirmative and just great advice giver, just a good, kind heart who spreads a lot of positivity, which is what I like. And every now and then she'll post a video how she's never had a boyfriend.
44:12Simon Sinek:She barely dates, but young, attractive, successful, doing well in her online influencer life, for what that's worth. That's a different conversation.
44:26Simon Sinek:and there's a sadness that this person who's in her mid to late 20s hasn't, forget about love, forget about relationship, has barely dated. And that seems to be more and more common. I'm meeting people in their 20s who've never really had more than a couple of dates here and there. what's going on? And I'm asking for the people who are listening who are young, but also for the parents of young people. Yeah. A lot of social skills have atrophied. Some of that is due to the pandemic. A lot of that is anxiety. And so the idea of going out in the wild at a coffee shop and approaching someone and risking rejection or someone not interested in you, there's so much anxiety of doing that.
45:19So why would I bother? I would rather just doom scroll or I'll do this other thing that will give me a hit of dopamine. And you do that enough times. And then you just don't ever do that thing of meeting someone in person or having the conversation. And again, I do think this is, there's a message that we need to avoid the uncomfortable feelings and bad feelings equals bad. And so they're not. You can get rejected and it's okay.
45:49Simon Sinek:Let's double click on that. Let's double click on that. That is so good. Bad feelings does not mean it's bad. Yeah. Right. Uncomfortable doesn't mean narcissistic or toxic. No. Just means uncomfortable. Yeah. All the advice that we're getting is about mitigating, blaming, letting ourselves off the hook. and very few people are giving us advice to enjoy and i mean enjoy discomfort anger depression um depression is only a bad thing if you get stuck in it if it's capital d depression that's a medical condition um it's perfectly normal and healthy to be sad yeah uh that it's part of being human to be messy and you can't be happy every day and I think the thing that I've learned as I've grown older, which is I saw negative feelings, bad feelings as somehow making me weaker.
46:48And that if I was happy and optimistic all the time,
46:51Simon Sinek:that makes me stronger. And what I've learned is, no, what makes me a great human being is that I have a range of emotions. I learned this in a funny way. I'm an art collector. I collect a lot of art, as you may see. There's a ton of it. And I bought a sketch of a dead bird. And it showed up in the mail. And I unscrolled it. It was all rolled up in the tube. And I unrolled it. And I had instant buyer's remorse. Like, what the hell do I want with a picture of a dead bird for? Like, I'm not going to hang a dead bird on my wall. You've got to be kidding me. And I was like, what have I done? Like, why did I buy this?
47:31Simon Sinek:You know? And by sheer luck, I had a friend over when the mail arrived who was an artist. and I'm expressing all my buyer's remorse. And she looks at me and she goes, a good art collection has a range of emotions. And in that moment, I fell in love with my dead bird, had it framed, and it hangs very proudly on my wall because my art collection has a range of emotions. And this is what I've learned about great human beings. You're getting me thinking. I'm connecting a lot of dots and seeing all these connections. But what I'm taking away from this entire conversation with you is the skill, the single skill that we all have to learn in order to succeed in dating and to succeed in relationships is our ability to sit in discomfort.
48:17Simon Sinek:And the single best way to manage discomfort is to learn how to communicate. Yeah. That's my takeaway. And I'll add on top of that is to be aware of the story you're reinforcing. Yes, the reframing and the mindset, yes. Because whatever you keep repeating, right, You go and you approach someone at the coffee shop or you DM and you get rejected. And then suddenly it is, oh, dating sucks in LA. Yeah. Right. Or these people are like this. Yeah. And you keep saying it over and over again. Or I'm an avoidant. I'm always such an avoidant in relationships. That becomes your narrative and your identity and your future.
49:01Simon Sinek:Really good. Really good. Not I am an avoidant or I have avoidant or anxious attachment. but it's not a diagnosis for heaven's sakes. Exactly. It's a, it's, I have had avoidant tendencies. Yeah. Yeah. I like that it's, you know, I have had avoidant tendencies, which is, it's a past pattern. It's not who I am. Exactly. Yeah. Yeah. Yeah. Yeah. It's not a predetermined, it's not a, it's not predestined. Predestined. Yeah. You're really good at what you do. Thank you. Good stuff. Amy, thanks so much for coming on. Thanks for having me. This was so fun. Absolute joy. I have to do a 10 part series of this.
49:37Simon Sinek:It went on for a long time. It was really good.
50:04Simon Sinek:Johnson. And if you want more cool stuff or just to find out what I'm up to, visit simonsynic.com. Until next time, take care of yourself, take care of each other.
From the publisher
The internet is flooded with advice for dating in the smartphone age: know your type, trust the spark, watch for red flags, protect your peace, never settle.
It sounds like self-respect, but relationship expert Amy Chan thinks it’s a big reason dating feels impossible right now.
Her argument: we need to correct the lessons we’ve learned when it comes to dating. The person who’s great on a first date isn’t necessarily great at a relationship. Instant chemistry isn’t always a good sign. A red flag could just be an imperfection. And keeping our options open has made a lot of us genuinely bad at choosing someone.
Amy is the founder of Renew Breakup Bootcamp and the author of Unsingle: How to Date Smarter and Create Love That Lasts. For nearly two decades she’s looked at dating through psychology and neuroscience — why we’re drawn to certain people, why relationships fall apart, and what actually predicts whether one lasts. She started her career helping people end relationships… Now, she teaches them how to build one.
In this episode you'll learn:
➡️ Why “instant chemistry” is one of the worst predictors of a lasting relationship
➡️ The quiet qualities research says actually predict a happy partnership
➡️ Why dating skills and relationship skills are two completely different skill sets
➡️ How the algorithm rewards red-flag advice 10X over green-flag advice (and what that’s doing to you)
➡️ Situationships: why the breakup hurts more when there was never a breakup
➡️ “Leaky energy,” micro-cheating, and the honest test for both
➡️ The 9-date experiment Amy gives clients who are stuck dating the same person
➡️ How the right relationship shrinks old wounds
➡️ Why discomfort is a critical skill dating requires
Amy’s advice isn’t about finding a better person. It’s about becoming someone better at love. And that’s advice all of us could use!
This… is A Bit of Optimism.
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This episode is brought to you by SAP. Bring it with SAP GROW. The AI Cloud ERP for any size business. Learn more at https://SAP.com/GROW
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To get a copy of Amy's book, Unsingle: How to Date Smarter and Create Love That Lasts, head to: https://missamychan.com/#books
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Chapters
Chapters
00:00:00 Why Modern Dating Advice Is Making Us Worse at Love
00:02:26 From Broken Heart to Breakup Bootcamp
00:09:50 Why Dating Feels Harder Than Ever
00:11:35 The Two Different Skill Sets: Dating vs. Relationship
00:12:26 Online Dating and the Imagination Problem
00:14:17 The Coffee Date Defense and the "Five Out of Ten Rule"
00:15:53 The Cure for Avoidant Attachment
00:18:13 The ADHD Love Bomb Confession
00:24:49 What Self-Care Culture Gets Wrong About Commitment
00:30:31 Situationships: The Safe Space That Keeps You Stuck
00:33:07 Leaky Energy and Micro-Cheating
00:35:08 Amy's Seven-Year Relationship and Emotionally Corrective Experiences
00:39:28 The Instant Chemistry Trap
00:40:59 The Nine-Person Dating Experiment
00:44:37 Why Young People Aren't Dating Anymore
00:45:49 Bad Feelings Don't Mean It's Bad
00:48:02 The Single Skill That Saves Relationships
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Simon is an unshakable optimist. He believes in a bright future and our ability to build it together.
Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do.
Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game.
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Website: http://simonsinek.com/
Leaderful: https://simonsinek.com/leaderful
Podcast: http://apple.co/simonsinek
Instagram: https://instagram.com/simonsinek/
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