Money and Dating for a New Generation

0:00Haley: Okay, so I just gave my apartment a major refresh and hands down the hardest thing to get right was the rug. I just couldn't find one that fit right and I really wanted something that pulled the room together because like a rug is a big deal. But then I found Ernesta and Ernesta is amazing you guys. It makes designer quality rugs custom cut to the exact size of your space so it actually fits instead of almost fits and looks great the first time. Like in the past, I've just defaulted to stock sizes when buying rugs. And also like when you're in a New York City apartment, that really just doesn't cut it, but they're all weirdly shaped.

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2:37Haley: So you put 100k of your own money into producing the special? Give or take, yes. My worst purchase of all time was the Kimo Sabe hat I bought in Aspen. How much was it, 500? You're being too kind. Oh, like$1 ,200. Stop. Like crazy. I think maybe, no,$1 ,500. Being in a relationship is an act of delusion. You need to be delusional enough to believe that you and this person are a love that can last forever. I have sent the post-shooting text to someone I've had a relationship. You've sent the post-shooting text. It is crazy that it says a lot about the times we're in. This is Financial Tea. What's up, Zippers?

3:18Haley: Welcome back to the Financial Tea. This is the podcast where I teach you how to build wealth with a side of market drama, money, scandals, and of course, financial pop culture. And today is a very exciting day in the studio because we have Jared Freed, comedian, podcaster, and Netflix star because his new special, The Family Plan, is out. It's so good. I was truly dying laughing. I feel like it's made for millennials. It just really hits you where it hurts. Thank you. And also my old neighbor, which I feel like we don't talk about enough. Yes, we lived at Soho. No, Ludlow Street. Ludlow. Was that Soho?

3:58No, that's Lower East Side. Lower East Side. That's where it was.

4:01Haley: Lower East Side. My one year on the Lower East Side. I loved it down there. So we always start with a few rapid fire questions. Okay. I think you're the first person I've ever heard say that getting the ick is only women get the ick and it's not relatable to men. And so if we were going to take gender out of the equation, can you give us your biggest financial ick in dating and your biggest financial turn on my financial ick would be a lack of passion oh that's um i i like women with like careers and and love their jobs and you know like i never related to like the idea of a woman with like a great job intimidating a man i never related to that lawyer doctor you know my my girlfriend she's a wealth manager like that's hot.

4:49I like a woman with passion and a career and just killing it. That really turns me on.

4:55Haley: What is the most that you've ever spent on a date? Have you ever done full omakase, send in the black car, or here's your little bracelet? I would never send a black car. Are you like... I would send a woman home in a black car. I think that's a fun touch to a hookup. Yeah. Because I got the Uber. um but the one time i'll never forget it i was going on a date with someone and my friend is like the restaurant guy he knows all the restaurants yeah and he was like you gotta go to this place in the west village it's like highly rated all this and i didn't even look it up i just like went and i took this girl it was like literally like a first date and it was so embarrassing i i the name escapes me it's a tell me about it or maybe it was a swedish fancy place in the West Village, like deep in the West Village.

5:49And I remember sitting down and being like, this does not match what we're doing on a first date. Like this should have been drinks.

5:58Haley: We're having tiny meatballs. It should be something shareable. And this was like, you know, silver platter in front of you, silver platter in front of me. Voila, dinner is served. And I was like, I am so embarrassed. And I remember I went to my friend who's married and he knows all the restaurants. And I was like, why would you send me there? because the only thing I saw on the menu was they had a pretzel. And he goes, what did you think? I would send you to a restaurant with a pretzel on a hook, like you're at a Dave and Buster's? I'm like, yes! That's where you send someone who's going on a first or second date.

6:28Like, this was, like, early date, and I felt so weird. No one eats on the first.

6:33Haley: Like, you don't eat for the first three months. That's what Cardi B says. I would eat. I'm eating. I would be... I want a girl eating on those first three months. Oh, really? What would we relate on? What would we talk about? Okay. And then what is the best and worst purchase you've made this week and how much did each cost? Because I know that you've been going all around town. You're promoting a special. The best purchase would probably be the$5 posies that like, it's like, you know, those like little white flowers. When you walk into Trader Joe's. Yeah, yeah, yeah. When you walk into Trader Joe's, they have that flower stand.

7:11there's one little tiny thing five bucks if you're a guy who's in a relationship i don't think for dating this will work because for dating it looks like you're trying to pull a grift but if you're a guy who's in a relationship you're committed with someone and you say i'm going to trader joe's and you come home with that five dollar little pansy white you know fluffy things that$5 gets you so much mileage as a good boyfriend.

7:40Haley: The great ROI. No better ROI than the$5. Whatever that$5 flower at the front of Trader Joe's, if you come home with it, if you bring it back, oh, I got the shrimp crisps and the salsa and the chips, and oh, look at that, I remember, here are some posies. they're going to react as if you brought back the head of a lion to your cave and you have done the greatest thing on earth so that's the best purchase then do you have a worst purchase the worst purchase this week my worst purchase of all time was the chemo sabe hat i bought an ass no we need to let's like dig into that a little because the chemo sabe of it all like they really that is a grift where they're like you're in aspen you need to buy how much was it 500 so you're you're being too kind it's the kimosabe experience is by the way there's like pictures of rihanna meeting jeff bezos at kimosabe like it is and he's on a horse yes he's on a horse like i'm not even like he's you can find this picture jeff bezos walks into kimosabe on a horse here's the thing about Kimo Sabe it is you have to treat it as if you are walking into a used car dealership because the women working there are all like pretty and cute and they're like want a shot and then you're like yeah why wouldn't I want a shot and they have shots ready made to Carlos and Charlie's they do a shot ski you're taking a shot ski and I remember walking in being like there is no way I am ever gonna walk out of here New Yorker with a stupid cowboy hat on my head and then I took one shot the girl put a beer in my hand and she goes just put it on and I put it on I go and she's like it isn't bad they even know how to talk to you yeah to make you feel good because they'll go I you know I don't hate it they go yeah I don't hate it I didn't think it would work yeah yeah and you're like I don't know I'm not gonna be that guy and then they go try the other one and by the end of that experience you know it's like I've always said this about massage, massage places.

9:52Oh, I love a massage place. Love a massage place. But all a masseuse has to do to make me feel like it was worth the money is to whisper in my ear, oh, you really needed this.

10:03Haley: Yes. Oh my gosh. A hundred percent. To give you. Yes. You were really tight. You don't. You were. Yes. They need to give you like the little, like the something at the end. The rationalization. They need to like. I can do it at like a juice bar place if I don't feel well. I'm like, what's good for the flu? And they're like, oh, this is going to cure you. All they have to do, one touch of helping you rationalize. And it's like, that gets you the bigger tip. That gets me the better experience. I'm coming back. I would actually go into a massage parlor and not get a massage and then just have them go, you look tight.

10:38And then I would walk out and I would feel better. I would pay 20 bucks for that.

10:41Haley: Five dollars. So they do that at Kemosabe. They do the... So they juiced you. They liquored you up. They liquor you up, they put the hat in your head, they go, ah. They go, I didn't think it would work, but it's not bad. And then they put another one on you and they go, no. Oh. No, you can't wear that. That's crazy. They've got it down. And then they put another one on. By the end of it, you're going, do I get rabbit or beaver? And do I need both? Right. Well, then you start going, rabbit doesn't last as long. No. So it's a better purchase to get the beaver because that will last you longer. And I do want to have this hat.

11:15Forever. At my wedding and my retirement party. So I will, this is a lifetime purchase.

11:20Haley: And it's something I'll be wearing every day. Yeah, it was the dumbest use of money. But again, it's those Asp, it's the air in Aspen. The Aspen air. Right. Wait, so how much was the hat? Oh, like$1 ,200. Stop! Like crazy much. Jared! I think maybe, no,$1 ,500. Where is it now? $1 ,500. Because then you start putting the accoutrements. Stop! You put the belts. It's like getting a crock with all the gibbets. Yeah, oh yeah, you gotta get, you can't just get a hat. Now you got to get the gator belt around it. You got to get the feather and that comes free. So, whoa, we're getting it for free. I got to do it.

11:52Then, hey, we'll put some, we'll burn some letters underneath the, you know, the cab. And it's for free. You go free. Why not? You got a couple of beers and a couple of shots in you. And you're like, listen, I'm an Aspen, baby. Yeah. And that's the problem with any vacation mindset is like, I'm never going to be back here.

12:10Haley: But let's go back to your special because something that I actually found it to be really rooted in finances, obviously family plan. It's about being on your family phone plan, but also even within the special, you talk about, uh, you know, how we're the first millennials are the first generation to earn less than their parents. And so it puts us in the position where we are reliant on them. And in some way or form, I don't think, I think some way or form you're more reliant on your parents than maybe your parents were reliant on their parents. Yes, exactly. With this grim reality that millennials are the first generations who are going to do material worse than our parents, how do you think that affects our dating lives?

12:56Because there's a lot of data now that dating is so much harder than when our parents were young.

13:02Haley: The rate of single adults has been climbing. So I'm just curious if you think there's a tie to that. Yeah, of course. There's a thing called the Hope Index, I think. Hope Index in the U.S. is very low. I don't know the number, but I'm referencing something like, I don't think we live in hopeful times. So if you don't believe that your career track is taking you towards the ability to have the things in life that you'd like, it's way better to live as a renter in everything than it is to live as a buyer who's stuck in something that maybe they wouldn't be able to afford in the future. Yeah. And being in a relationship is a version of buying.

13:41So interesting.

13:42Haley: I love that. Right. That's why millennials, we do a lot of blaming everyone for like, oh, we can't buy homes. But a lot of that is our own fear of ability to earn later in life. And the boomers aren't exactly retiring. They're working forever. So again, you're now being held, Gen X, millennial being held in kind of one space with no upward trajectory really in sight. I can understand how hard it would be to say. Doesn't make you feel confident. Yeah. And being in a relationship is an act of delusion. You need to be delusional enough to believe that you and this person are a love that can last forever.

14:24And, you know.

14:25Haley: So interesting. So true. Do you feel like that with your girlfriend? Oh, I feel that way with everyone I've dated. You need a good mix of logic and delusion to be in a relationship or to be single. You kind of have. And I think as I was single later in life, I got more logical and less delusional. and how did that look like what is that materialize well because you go i'm not gonna dive in with someone to let them down in the future because the odds of us being something real is very low why it hasn't worked before why would it work now you know and you become safer you become safer not to hurt other people in the way you've hurt people in the past because maybe you dated someone like for my case i was someone who ended relationships so i would be in positions where I'd end things before the next step.

15:12So the ending before the next step.

15:14Haley: Just because you knew this is not going to go anywhere. I don't want to disappoint them. I wasn't delusional enough about the relationship itself to push through to the next level. And that's a measure of logics of going, ah, you know what? You know, I can just, there's way less asked of me as a single person. There's not a lot asked of you as a single person. It's expensive today, but cheaper in the long run. Yeah, it's very expensive to be single, but also like you buy a lot of freedom. Right. Well, it's cheaper emotionally. Yeah, so much cheaper emotionally. You know, I think something that's similar between us and our work is that we've both had a lot of takes and opinions on dating over the years.

15:57Haley: Obviously, mine about finances, but yours about, you know, interpersonal dynamics. And I shared a lot of those while I was single. you did too and now you're in a relationship I'm in a relationship too and do you feel like any of your advice are you confronting it for the first time and do you feel like it's you know actually holding up I never like I tried my best to not to stay away from like telling people what to do I would always tell people what I felt in the moment so like you know for me in a relationship I'm I'm not really faced with my advice as much as I'm faced with new emotional spaces you know I'm more faced with like oh this feels good to be in a relationship to share this with someone it feels you know oh my god I gotta you know when I talk on a podcast or do my material how I care for someone else and how I you know think about that you know how I put that out there that's all stuff that like is new to me and like worth acknowledging and you know there is such a jump from when you're dating someone to when you are in a relationship and I feel like you really feel it financially because there's, you know, when you're dating someone, maybe you're taking them out to dinner and like you're, you said it's a cute touch at the end of the day to send them home in a black car, all those things.

17:10Haley: But then as you relationships become more realistic and it does become, you know, you're actually splitting groceries, maybe you're splitting rent, like it's almost more industrial. And so can we talk about how you see that transition happening in relationships with finances? And do you have any feelings about how you can make it smoother? because I feel like it can be difficult. It's definitely difficult because money is so emotional. Yeah. I like my kind of going policy has been to just be curious. You know, like when you do coaching, like I'm sure it's a lot of questions. Yeah, it is. You know, like you have to know everyone's financial position is different, their ability to save and to spend and how they feel about saving and spending.

17:54So, like, I think just a lot of questions. Like I, I just like, all right. Our first question was like, I was like, how much are you paying in rent? Like that was like a little bit of an easier thing. Cause it kind of got the ball rolling, but like just understanding, like, you know, everyone has so many insecurities around money, you know, again, like who's on the family plan. No one answers. Like that's an insecurity. That's, I don't know what that is, but I think questions, curiosity, be curious. That's my, my policy.

18:24Haley: that's really good advice i think that's such a great way into these money conversations that are so difficult versus being like hey we need to talk about this thing being like oh like how do you feel about this right and it doesn't have to be just numbers it's just feelings you know like the numbers you know they can be tough because and the other thing is some people just don't know their numbers and are embarrassed they don't know those yeah like they get embarrassed so how much you spend on groceries a month i have no idea is it a trader joe's month is it a whole foods month. I just think it's worth acknowledging how emotional it is and how tough it is.

18:58That's really good advice. College debt, that's an emotional thing. Talk about generationally. If you have college debt for a degree you're not really using, there's just so many... There's so much to this.

19:10Haley: Credit card debt for a credit card that you got pushed into getting maybe at that first fair in college. Just all these things because it's an industry that definitely benefits off of people's ignorance. Right. And it's never taught. Okay. But back to the special, you self-produced it. So you put a hundred K of your own money into producing the special. Give or take. Yes. Yeah. So how'd you decide to make that investment? I know it took a long time from concept to actually getting it out. Like walk us through this. Cause I would love to know how much a comedian actually makes from that book special.

19:46Well, my, you could, there's two ways to have a special. It either gets leased or it gets, you make it and then they lease it from you for two years, which is the deal I have, which is$220 ,000. I also made a deal with Betches to be the co-producer so that they would promote it. That's so smart. Well, it was the thinking was at a minimum, Betches would push out wherever it went. And maybe that would help me to sell it. Maybe that would help me just in general. it wouldn't get seen by nobody just off of my ability to go on podcasts. So it was really an act of insecurity as far as like, well, if no one buys this, what's the bottom?

20:29What can I assume the bottom to be? And the bottom being that that's just a huge media company that I love being somewhere that could promote it to their fans that are already have a relationship with me. So, But then that means giving them like 50 % of what's left of the 220. But also, you know, you got to hire PR people. You got to hire, you know, there's other costs. I go to LA. I come to New York. I live in Delray Beach. So, you know, as far as the money from the special, that's it for me. Like, it's not really, the special to me was a way to find new people. Like, I want people to watch an hour of me and go, I got to go see them live.

21:09You know, it's kind of like the music model. come see me live as opposed to buying the album. Like, let me put it out on Netflix on a huge platform. Hopefully it catches fire. And I'm proud of it. I guess like the advice to anyone who's doing stand up and producing their own special is you better be able to like, uh, be proud of it. Like I, you know, every comedian knows the jokes that work 100 % of the time and the ones that work 50 % of the time. If you have a special that you're like, I, you know, maybe it's not worth putting that much money into it.

21:40Haley: Yeah. Oh, yeah. You have to be real with yourself. You have to do your diligence on the investment. Like, oh, if I'm going to put$100K into this thing, is it actually – that's how I feel about the S &P 500. Because it's like 100 % of the time, if you keep your money in for 20 years, you're going to make money. Right. But you got to have the – you have to have the risk tolerance. Totally. And the timeframe. Right. You have to be able to say goodbye to the$100K for that period. and see the 100k to go down to 80k in the first day and then go i'll be fine yeah um and that's the same with the special i have to be able to see you know the the bottom is betch is putting out my youtube special and going i'll be fine you know because i believe in the material so much that if anyone watches it they're gonna go i gotta see more of this guy there you go it is i saw it um okay so i think that you being a comedian it's sort of this black box like the financial reality of it.

22:36Haley: So I would love for you to talk through for our listeners, some of the ways that you make money. Obviously you're super successful. Now you have your Netflix special, you tour, you have your podcast, you work with Betches, but let's go back a little bit. Um, you know, what was the lifestyle and financial reality when you were building and starting out and where are you at sort of now? I mean, the reality was that, you know, you start To me, I considered it grad school. Like, I'm lucky enough where I was like, I can spend, you know, I was working doing life insurance, annuities, financial planning stuff for like four years, three or four years.

23:19And I was like, this isn't for me. And I was like, I can, you know, it was kind of the 25, 26 where everyone's like, you know, you have that friend that's going to law school. yeah and you have to be fighting you know the friend that went to law school is probably doing like doing okay has a good you know backing a family too yeah so i had like literally like bar mitzvah savings in my bank account where i was like okay this would have gone towards going to grad school yeah or in some way or form and i was like let me put this towards taking classes and getting good at comedy like sketch writing um i'll go to do you cb i did sketch writing at ucb which was that at the time it was like tough to get in their improv classes i did chicago city limits for improv i did uh storytelling with a guy named adam wade who's like a fantastic

24:18Haley: storyteller unbelievable so even then you invest in your human capital you were like i'm gonna put money towards building my skills here. I've got some natural talent and I'm going to refine it and learn how to do this really well. Yeah. I wanted to get good at it. And I went to open mics every night and you know, the reality of that was like, I was very lucky that I could do it in a way that was like very much like, I'm going to go a hundred percent all day long on this. So like, you know, that was really the reality then. And then like, I was looking for really any opportunity I could get like you know as far as like ways to be funny for money whether it was shows or like you know there were like weird opportunities would come up where you can write tweets for a celebrity yeah you know I would write tweets for guys that you know that wanted to be funny at their you know whatever charity tournament and get stuff like that so really figuring out but also knowing like what my day-to-day was like I knew what it took me on a monthly to live and i was like and then i you know over time you're like okay what are ways to get myself out there and then podcasting at the time it really wasn't a place to make money like as ads are concerned it was really a way to talk directly to fans and i wasn't really getting cast in anything so i was like here's a way that i can like put my word out there and then i can also write and put myself on like i would put myself on different i would send like material to like places to put my name out there oh you can follow jared free and the social media started getting more and more so that was really the beginning of like doing and then starting the podcast i went to like i remember total frat move was like posting my stuff and i was like they had a million twitter followers and i was like hey do you guys want to i went and met with them when i was on a bachelor party in austin and i was like do you guys want to like do a podcast and they were like what's a podcast I was like perfect yeah and then I was like you promote it I'll find a production place and then I'll you know I'll host it and so we started that and we were like really teaching that audience about podcasting yeah and then I always said I was like if women just got into podcasting I think I have a show that women would like because we were doing dating advice and then that's how I met Betches because I started like sending them tweets and things that they could post and just really looking to get out there and hoping for someone to go, whoa, this guy's writing is really good.

26:39We'll get them involved with this. Or, oh, you submit for this show. That never really happened. More, what happened was the world kind of came to me. People started doing ads on podcasts. I was doing this yelling at The Bachelor. Oh, that was great.

26:54Haley: I love that. That was getting attention where people were watching my stories as if it was a show I was putting on. So that's kind of the way it worked out. Quite entrepreneurial though, like where you did sort of build it and then they came where you're like, okay, you got an audience. I'll do the podcast thing. Like, let's go. Yeah, it's all. I think comics are like the hardest working people that don't work hard at all. Yeah. No, you work so hard. But, you know, going back to this, you're talking about finding your audience and how you thought, you know, women were interested in dating. How did you sort of break into that being your niche?

27:29Haley: because you do it in a way that's so relatable to audiences i was just doing what i do and the idea that women would like what i do was like kind of a surprise um but i've always gotten along with you know just like the debate like i've always had women come to me for dating talk in general and then the show worked better when betches came on you know i would have them as guests and they were like we like a podcast we we want to start one of these and i hooked them up with producers to like help them start theirs. And then when they called me in, they're like, Hey, let's do a show where we're do the male female point of view.

28:03And that's us. You upstarted.

28:04Haley: I want to get back to dating because we all love your takes on that. So what sort of money realities have surprised you when you've been out on the field? I think for me, it was always hard to date someone. You know, I think it was way harder to date someone who was young with money. Oh, you know, I think like when someone's young and comes from money I think that was always like a more difficult dating scenario because you know that would put a rush on kind of what I was doing and I couldn't kind of provide that way I noticed that like when I was dating around you know I'm doing comedy I'm like 27 28 and around that age you know I I think that's like when you're 27, 28, I've always believed you can always cancel on a 25 year old woman or a 34 year old.

29:05Because they're like, thank God. The 25 year old woman, she's like, I'll go hang with my friend.

29:09Haley: Yeah. I got a whole group. The 34 year old's like, I'll take a bath. Yeah, totally. You can't. You will you will rue the day you cancel on a 29 year old. because she's faced with like a whole group where people, especially when you're dating and you're taking it seriously, like you got the ones that are starting to get married and engaged and the ones that are getting left behind. You're like, I don't want to be the left behind one. I want to be a married, engaged one. And it was always tough for me because I could see that when I was dating someone around that age or that I was around that age, especially cause I was, I wasn't dating, you know, younger or whatever.

29:46I was dating my age and they, you could see that like, I was like, I can't do the next financial step and feel comfortable about where my life is.

29:57Haley: Yeah. And I think that gets underrated. I think that gets vilified on the male side. And, you know, I do think men want, you know, they want to provide, they want to feel like they are valuable. I think everyone wants to feel valuable. And I think, you know, part of what makes a man feel valuable is the ability to do the next thing and be running towards the next step. And I always wanted that. I wanted to like sprint towards the next step and women find indecision horribly unattractive. So the, Oh, you know, what do you want to do? I don't know. I can't commit. Like that's all not hot to a woman.

30:39so for me it was always like i could always just feel that and i think with people who were like used to a certain lifestyle i think they were also not willing to go through the

30:57Haley: the grind of it all do you think that they would you have felt comfortable with a woman supporting you though like if you had met a like one of those young girls with money no because then you know what do they say about dating a rich person date someone the most expensive thing you'll ever pay every day of your life yeah yeah yeah i never wanted to be in that situation and some people do some people go yeah yeah i'd rather have two houses i have a friend like that right she's like looking for it and i celebrate it i'm like okay you know what you want right i think i I don't know if a man would be celebrated as hard because he'd be like, well, what is this guy doing?

31:38Haley: Yeah. You know, he doesn't work. He's a comedian who hasn't had anything happen for him. Yeah. You know, like it's like not a great look and not a great feeling too. I wanted to feel. Yeah. You know, observe the North American dad, fifties, great polo collection. He enters his vehicle information on Carvana and offer appears in, minutes. Remarkable. He squints, reads it again, smiles and says, dang, that's a good offer. The highest form of approval. No haggling, no hassle. No one called him boss. He's still on the couch. Astonishing. Sell your car today on Carvana.com. Pickup fees may apply. Wired has always put a microscope on the people, power and forces shaping our world.

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33:14Haley: So you say though, that maybe like something that holds people back from taking the next step in relationships is financial readiness, especially when you're a man but i feel like that's never the reason that's given when you're broken up with it's always like something else and so do you think you don't think they give that reason have you have you broken up with a girl and been like it's because i'm not rich enough i would think it's like i'm not ready i'm not and no but i'm saying that's so i think that's like what a guy's saying when he's saying it's not ready you oh interesting i think that would be right how long have you been with your boyfriend uh for five months five months yeah how did you guys meet on hinge on hinge what does he do he works in finance works in finance could you see yourself dating someone that didn't work in finance i mean i've dated comedians i've dated like so many different kind i like i dated people who i thought were interesting which then led me towards people who were often broke well that's the thing you laugh but that's so funny but that's funny that like you know you're asking they never say it up front that they weren't financially ready to you know be ready for that but like you like you would be a tough person to date in that scenario yeah i know i think it was definitely intimidating for a lot of guys like also because there's this idea that maybe if you date mrs dow jones you have to be super rich right but also mrs dow jones goes to the hamptons house and martha's vineyard family though family money yeah got to keep up you've seen you're not gonna live a lifestyle i would it would be tough to believe that your lifestyle is going to be any lower than your parents while dating you but went to summer camp yeah no no i'm saying all these things like private school private school yeah yeah so like all the you vacation right so it's like i think like from the perspective of like no it's a big pill to swallow you gotta want to go there but i also think that what's different is that I will put my own oxygen mask on first.

35:12Haley: Like I've never looked to someone. I've never gone on a date and been like, great, this is who's going to pay for it. I'm like, how am I going to pay for it? Right. But you've also had like the backing. Oh, of course. No, no. I just think like that's also in like it's a cause and effect thing. Like you had the money so you can be more confident about money. Yeah. So like I think if like I just think like the idea of like why don't men get in front of whether they're i think a lot of men believe they could be in a day in a relationship like they're like i think it gets it's easy to be like well he said he wanted to be in a relationship then all of a sudden he does no now he doesn't want to be in a relationship with you you know we dated we saw each other it was great now i'm being face to face with the reality of stepping into this future the reality of stepping into this future is finding out that oh my god i gotta date someone who has all these things going on that i don't think i can keep up yeah you know and i don't think i can keep up with the track that's laid in front of me while also again you dated comedians no i did i remember i was doing this guy who lived in bush with like three roommates and we went to the bodega and i got a pellegrino and he like thought it was the craziest thing in the world like and it was i didn't that factors in yeah you getting the pellegrino not a big deal not a big deal not a big deal in the scheme of life no but it is a personality yeah it's like oh shit like there was a difference in our yeah how we spent money right if he looks at a pellegrino and goes oh my god that's like a different life yeah you know so i think that's different that's a bridge to a new world totally so first you drink the pellegrino then you're in the Hamptons.

36:57Haley: Next thing you know, you slip and you slide, you're in Kimo Sabe. Well, next thing you know, you're being told, why are you being a comedian? It's not working out. Yeah, you need to go get a job where you can put money, put food on the table. What are you doing? And you lose kind of the ownership over your own life. I'm sure you felt this dating a bit where it's like you have a big digital footprint where you talk a lot about dating. So what did that impact? It made it harder to like go to the next level with someone because I have to talk honestly about my life and I think what would happen was I date someone and I'd get to a point where I wasn't ready to jump through the next step but I was still dating someone and you go on a podcast and you talk about your dating life it would feel like I was lying to someone yeah even though we were like on the same page we communicate it doesn't matter how much you're communicating with someone, Hey, you and I were in this space and I'm not ready for the next thing.

37:57And they're like, no, I'm cool. I just like to know that you're off the apps and, Oh yeah, I'm off the apps. And then you go on a podcast and you're like, yeah, so single life. And now you're like, I would feel badly. It would, it would make my stomach turn. So it was hard for me to find the timing of it all to get someone to go to the next.

38:15Haley: how did you know with your partner now like i i feel like it was impacted a little bit too by you clearly are attracted to her ambition and like her stability she and i dated years ago oh wow and then i had to end it because i just wasn't there and i you know how old were you when you guys dated 37 oh wow 30 no 38 38 and then i was just i wanted to be there i wanted to have the confidence to go to the next step and I just didn't have I said to her you know and then we didn't talk for two and a half years so now that your career is in a like this like awesome place now is that where you got the confidence from like no I think it was more assessing what I wanted from life I spent two and a half years we didn't talk we were it wasn't a you know she I wrote a book the the red flag walking red flag the book was not telling you how to date it was getting you inside the mind of the red flag you might be dating yeah and why can't he give you answers what so it was being it was a vulnerable storytelling book where i'm like here's how i felt in this scenario and a few of those stories were about us her and i and was looking back at it so i had been thinking about her and then she ended up reaching out to me and i was like i was like literally debating whether i would text her or not that's so interesting that's for sure yeah I I like to think that it's uh like I think the messiness of our story is beautiful like I I think it's what makes it interesting I think it's what it's worth telling because you know I I'm really uh I really have a lot of uh I'm thankful that she had you know the the confidence that I didn't you know a lot of people look at texting someone that used to date is like a negative or maybe they could say it is and you know they'd sound like a smart person but like i think trying is the most admirable thing of all so as far as relationships are concerned as far as putting out a special and paying for it yeah if it didn't work out at least i try you know and you know i put a lot of effort into everything i do and then it's the coolest thing in the world is to try and to like and to totally eat shit and take the risk that that might happen is the coolest thing in the world like being apathetic is really it will lead to depression i think yeah well yeah well you gotta yeah i will say the weirdest text i've ever sent to an ex is i had a ex who worked at blackstone and they had the shooter that came there and i was like fuck like do i text him like that's really scary and i was like i think i asked chat gbt like how do i text my ex who like there was a active shooter in his office building we did not get back together i think he was like yeah it was really scary like thanks for reaching out yeah i think that's like an adult like like you were worried about him it's okay you can worry about someone you don't want to get back together with i'm like just so it's clear like this is not like a getting back together text just want to make sure you're cool like i have sent the post-shooting text to someone I've had a relationship.

41:33Haley: You've sent the post-shooting time. It is crazy that that's, it says a lot about the times. It really does. But it is crazy to me. Who did you send her to? There was, I don't want to get into specifics. Like what was the shoot, like what was the shoot? It was just a tragedy. I don't know. It was horrible. But it's crazy that I relate to that. Because I texted someone that I had been on dates with and was like, I just want to make sure. Like, yeah, you do. do it's crazy because this is the humanity of it like this is where like a lot of my day you know if i'm to be accused of anything it's to be too empathetic to the villain yeah not the villain in the shooting that's i'm not empathetic to them i'm saying to my own like to what you're saying of like what do i send the text to someone yeah where you're thinking of yourself and you're like i don't want to seem this way but also there was a huge fucking tragedy yeah but that's everybody You know, like, I think that's a more human thing that the, the losers in the comment section will, they'll go, what a, oh, he's thinking about yourself when it comes to the shooting or, you know, or whatever.

42:44Like it's, but that is a real life. That's why I love hearing real stories where I go.

42:50Haley: Well, because the dating is so weird because you got really close to someone and then you're supposed to just be like, never talk to them again. And if you do talk to them again, then you're desperate. and then our parents talk to you again totally in our parents generation it was more of a straight line from dating to relationship to marriage to babies to house where we have these kind of zig zag routes so it's like you know the situationship is a product of an extra four years the age of first marriage versus a decade ago is four years older that's a huge number it's huge to jump yeah So you go, what do you do with that?

43:23You got to fuck. Yeah. So you're going to have, you're going to have a lot of weird conversations. So, you know,

43:30Haley: on that trail of girls who might be involved in a shooting that you have to be like, Hey, I am worried about you. I hope you're okay. But I also don't want to get back together. Yeah. Here's a picture of me and my new girlfriend, by the way, you good girl. Right. It's crazy. Like it's crazy. That's why this conversation is a bone to be chewed on. You know, like i it is a worthwhile conversation because but it's it's funny how it gets shouted out like that story is like very funny to me it's so funny i also love but i think that something that you do so well is you give us a purview into that male vulnerability and like thoughtfulness because so much of the uh what's talked about with men with dating is like oh like he doesn't care like there's no feelings or just you know and like you you make it so human well also and even the stuff that you said about money i found so human where it's like you know men should admit that like where it's i appreciate that but also we're in a world of punch up punch down i mean you play the algorithm game oh yeah when you talked about those extremes i'm like i should be more extreme but it's scary i'm not that extreme of a person like i i actually am logical but also like you're a lot of your stuff is like women are dealing with this you're playing the women game oh so like i'm so excited about the lululemon divorce because they have no prenup which is like no prenup how messed up is that that's where my brain rot is yeah the guy who founded lululemon is getting divorced and there's no prenup and i'm like great content gold i mean and people hate him they hate him he has the microplastics it's rotten our vaginas yeah but he also he also said um but even that yeah you're going i'm doing it right clip it rotting the vaginas he's killing women yeah he's killing women and he has no i hope that she takes him for all he's worth he's also said that women with like bigger body shouldn't wear his clothing like that's like to me that's the most that's the worst part yeah yeah not the pfas it's about the sizes i don't even know about that yeah yeah no so like i i don't know i i'm okay with giving you're so right but i don't i think a lot of men are in a position of power dating you know because they're not rushing so true so so yeah there's no rushing power dynamic of like a guy not rushing and like that is acknowledged but i i think that's also why a lot of women get pushed into woo-woo scenarios and don't hear from a lot of men because it's not worth it what do you mean woo-woo i think men online if they are all you hear from online about men with dating generally are just angry men or you got like those coaches who You are like, if he does this, then ladies, he'll never talk to you again.

46:08Haley: Right. It's all just grifty shit. But when you're in one of those anxious situationships, you eat it up because it hits you right where it hurts. Scratching the itch. Yeah. Well, I'm really glad that we were able to relate on texting an ex about a shooting. And I really feel like we landed on something there. We got there at the end. And Jared, you are amazing. I'm so really love your special. Thank you so much. If you guys want just like something to watch that's going to make you laugh. It's so smart. Watch with your parents. Yeah, watch with your parents. Your parents are in it. They're in it.

46:42My parents are in it.

46:43Haley: Everyone is, all these millennials, they're using their parents for money. You're actually putting your parents to work. And that's a beautiful thing. And I'm working for me. That's right. There you go. Comes back around. We're flipping the coin. Thank you for having me. It was great. Don't forget to like this episode. Subscribe to the show. Rate, review. It helps us so much. We'll see you next week, Sippers. Stay rich.

47:07I'm Jenna Fisher. And I'm Angela Kinsey. And together we have the podcast Office Ladies. Just because we finished rewatching The Office does not mean we're going anywhere. Every Wednesday we'll be sharing even more exclusive stories from The Office and our friendship with brand new guests. Plus, you can revisit all The Office Ladies rewatch episodes every Monday with new bonus tidbits before every episode. So follow and listen to Office Ladies on the free Odyssey app and wherever you get your podcasts.