James Sexton on Sex, Cheating, Prenups & the Biggest Marriage Red Flags

- Anytime someone tells you the story of their life or their relationship and they're the hero of the story, be skeptical. Like I believe in the form of monogamy where I have sex with as many people as I want to. And ideally that's one. - That's a good one. - And people who are happy don't cheat. Like people cheat because there's this connection. - What's your most controversial piece of dating advice? - Talk about prenups really early in a relationship like third date. - Ooh. - Yeah, I did have a prenup where for every 10 pounds that the bride gained, she would lose $10,000 of Alimony a month. Yeah. - Wow. - And that was that was enforceable prenup provision. - Wow. - That court upheld. - Yeah. - The judge actually said this is a bullish provision. It's disgusting. I don't know why you married this person, but it's abiding an enforceable provision. (upbeat music) - Today's guest has spent more than two decades watching relationships fall apart, which might make him one of the most interesting people to ask about how to make one actually last. James Sexton is a New York City divorce attorney bestselling author and one of the internet's most recognizable voices on love, marriage, sex, infidelity, and white relationships fail. We'll be asking the questions we probably should be asking before we say I do. What makes someone great to date, but terrible to marry? What red flags actually matter is chemistry enough, and can you tell too early on if a relationship is built to last? James Sexton, welcome to Love, Sex, LA, unfiltered. - It's great to be here. - I'm so excited you're here. - I'm excited to be here. - In New York with the NYC divorce lawyer. - I love it. I love that you came all the way to the East Coast to hang out. - Yeah, it's very iconic. - We need some West Coast exports to come by and keep us grounded every now and then. We would just stay in the office all the time if it wasn't for you cool West Coast people visiting us and reminding us that there's like interesting things in the world, so. - Oh my gosh, well I'm so excited you're here. We're gonna be unpacking a lot today. - It sounds like I listened to the agenda you just ran down. And I was like, well, we're covering a lot of ground. I'm gonna do my best. I'm gonna try to keep up. - All right, I'm excited. We start every episode of the game. It's called date or ghost. And basically I'm gonna give you a scenario and you tell the audience whether they should date that person or ghost that person based on the scenario. All right. - Let's go. - Let's do it. Okay, they're extremely close with the next, but it's completely platonic. - I date that. That's okay. Yeah, I wouldn't step away from that. I think that you have to be comfortable setting a boundary of like how much contact they should be having with that person and what the nature of it should be and what your involvement should be, but yeah, I don't think that that should in and of itself be considered such a big red flag. I think that it's actually for me when someone has a healthy relationship with their exes, it tells me something about how they view relationships as chapters in a long book instead of like success or failure. It bugs me out when someone goes from, "Oh my God, this is like the best person," until like I absolutely hate them. It's like, "Wow, I get what lash watch in that." - Right, totally, I agree. They've cheated in every serious relationship, but they say they've changed. - That's a tough one because my instinct is to say ghost 'cause I do understand what people say about once a cheater always a cheater and a person who leaves, you know, the old saying is a man who leaves his wife or his mistress just creates a job opening. But the truth is, I think some people learn lessons the hard way. Like they have to step on the rake. They have to burn their hand on the fire. And so sometimes people learn about the pain of cheating and the pain it causes them and their partner and the third person, the hard way. They have to go through it. And so I do know some people that learned a lot about cheating by being cheated on or being the cheater themselves and seeing the side effects of what that caused. And there are people, I consider myself one of them that sometimes has to learn lessons the hard way. And so I think if this person is genuinely approaching relationship differently and they're being candid and honest with you about the fact that this is a trouble they've had in past relationships, I don't know, it could be a teachable moment for somebody. I believe in redemption. - You do, okay, I like that. We like redemption. - Okay, they tell you marriage is just a piece of paper but they want to spend the rest of their life with you. - I mean, for me, that's date. That's it, I love that because I think it's honest. Marriage is a piece of paper. I mean, marriages at best are attempt to dig a moat around the castle of our relationship and hope that it'll keep the world out. It doesn't really work. I can tell you that firsthand having watched thousands of marriages implode and fail catastrophically. But I think there's something really beautiful about the fact that we think love is so worth preserving. So I think when someone says honestly, yeah, the marriage is just a piece of paper, I think it's true, like it's a leading status. That's all it really is. It's a contract. It's a contract that you and this person enter into with the state and with each other. Most people don't really understand what legal rights and obligations it confers and how it changes the relationship. But I think when I see two people who've been really happily married for a long time, I very often think to myself, you know, if they didn't get legally married, I don't think the wheels would come off the thing. I think they love each other. And I think marriage and love correlate sometimes, but I don't think there's a causal link. I don't think that if these people didn't take the plunge and get the government involved, they would have fallen apart. I think that love is a promise of its own and marriage is just another way of like confirming that promise. But I don't know that it really is like the bulletproof vest we would like it to be. - Yeah, well, and you were married before, would you ever get married again? - No, I don't think so. It doesn't have importance to me. - Yeah. - The reason I say I don't think so is if it was very important to this other person for very tangible reasons that made sense to me. You see, I'm a believer in asking the question, what is the problem to which marriage is a solution? - Yeah. - And I know it's considered kind of indelicate. Like if somebody, like if you said to me right now, oh my god, Jim, I'm getting engaged, we're gonna get married. If I said, oh really why? That would be kind of a rude question. I don't think it should be. But I think that it should be okay to say to someone, hey, you're about to sign up for something that catastrophically fails more than 50% of the time. It's pretty reasonable to ask a person why would you do that thing? If you're happy and you're connected to this person and you found them out of the eight billion other options and you're really enjoying each other, why do you wanna get the government involved? Why do you wanna get lawyers potentially involved? Like why not just be happy with each other? Now there's a sensible answer. It's important to me in my religion. It's important to me in terms of the tax breaks. It's important to my parents and I wanna make them happy. Those are all pretty good reasons. And they're tangible reasons that vary for some people. Some people might be very religious or very family oriented or we want our children to have parents who are married to each other. These are all reasons, they're intentional. I just tend to believe people's lives should be by design not by default. You shouldn't just, why'd you go to college? Well, 'cause that's what you do. Why did you get a job right? Why'd you get married? Well, we've been together a while, that's what you do. I don't buy that and I think that that's a recipe for unhappiness. Yeah, well, and you mean it's such a good point too. Over 50% of marriage is fail, right? Yeah, well fail catastrophically. Meaning you get divorced. Like, think about, there's another, and again, the research is mixed on this, but there's another 10 to 17% where you stay married legally, don't get divorced, but you're living separate from each other, either with a separation agreement or one of you just went out for milk and never came back. But you didn't finalize a divorce. Then there's another cohort of another 10 to arguably 20%, where you stay together and you're unhappy. But you don't want to give away half your stuff or you don't want to have the financial means for the two of you to move out. So really, if you think about it, we're talking, if the goal of marriage is to stay happy together forever, you're talking about 70 something percent fail to achieve that objective. Wow. That's a pretty bad grim statistic. But here's another statistic. 86% of people who get divorced, so meaning they've had a catastrophic failure of a marriage, 86% of those people remarry within five years. Wow. So that tells me something, and that is, we love this for some reason. Yeah. It's important for some reason. We just keep taking shots on goal, and I think that's something really admirable about that. It's something beautiful about that. 100%, 100%, I have an uncle who always says, so would you get on a flight if it had a 50% chance of crashing? 100% not. Well, I always say to people, if there was a 56% chance that when you walk out of this room, you're gonna get hit in the head with a bowling ball. Yeah. You would either not leave the room, or you'd definitely wear a helmet, which is why I always say to people, I'm like, this is why pre-nups make sense. Yeah. Because there's such a high percentage of marriages that catastrophically fail. Why would you not take some precautions to have an orderly exit strategy? Totally. And we're gonna be talking about pre-nups today. Sure. We're gonna be unpacking it off. Okay, they say they can't commit until they take it for a test drive. I would wanna know what a test drive means. Because, you know, I think there's a school of thought that would say you should have some sense of what this person's gonna be like sexually, or what they're gonna be like to live with. I think there's potentially value in that and logic to that. Do I think that you should transgress your own morality, your your own religious faith, your own, you know, whatever moral sense you have, just so you can audition for this person, I don't, I don't think that that's a fair ask. But I do think there's a logic to saying, hey, I'd like to see, you know, I watch some of these shows like The Bachelor and like, you know, married at first sight, you know, all those different shows and people are, you know, in like these beautiful vacation spots and they're like, oh my God, this is so romantic and it's like, well, you're on vacation. Right. It's really easy to get along with someone in vacation. Like Saturday gym is really chill. Like Tuesday afternoon gym is a little intense. And if you're going to be cohabitating with me or marrying me or having a serious romantic relationship with me, I want to know that you can't, like you're not just signing up for Saturday afternoon gym. You're signing up for, you know, Tuesday evening kind of stress gym. And by the way, I'm not just signing up for like hair done perfectly, makeup done perfectly in the best mood. I also am signing up for like PMSing kind of stress, not wearing makeup, feeling kind of bloated girlfriend. So isn't it okay to say to each other, hey, I want to see you at your best and at your worst before I say it's going to be you, you and only you. Yeah. I think that's a great point though, right? And I think anytime you sacrifice like your own values or you're doing something out of just pressure, right? You know, that's when you're like losing yourself. Well, and also asking a person to do that says something about how you're going to relate to them because I, I don't know that I want to be with someone who would put me in that position is going to say, look, I, I need you to transgress your morality, your values, your faith, whatever it might be, whatever informs your moral choices or your structure, right? Your code by which you live. Yeah. I think whether you're religious or not, I think people have a code, people have things they do and they won't do. Yeah. You know, and it may not be rooted in anything other than tradition. You know, like I, I, I stand up and give my seat to a woman on the subway. Like is, is it rooted in anything? No, I think like you're probably, you know, you're younger than me, you're fitter than me. So you could probably stand easier than I could. I'm my back hurts and I'm getting older. So, you know, it might be nice for me to sit, but I come from a tradition and, you know, I, I tend to, it makes me feel good to have that gesture of bravery. So I, I think that it doesn't have to have like a structure behind it. We all have things we feel comfortable doing and not doing. Part of being in a relationship, I think, is like meeting that person where they're at and not trying to put them in a position where they have to transgress their own morality without having had some discussion about, okay, what are the trade-offs we're willing to make for each other? Yeah. And, you know, I, I, I think that's a, that's a really important conversation to be able to have. I think so too. I love your answers, by the way. Thanks. And I love that you stood up for someone on this subway. It's one of my favorite things to do. It's kind of like, because I think it's unexpected now, like we, we sort of stop doing some of these things. And, and when you do it, there's, sometimes people are just like, oh, no, I'm fine. You know, which is okay. Yeah. But very often there's this like little bit of delight of like, oh, thanks, you know, and as a man, to me, that, that's one of like the nicest feelings in the world. Right. So like, have someone sort of react that way. Like, oh, that's nice. Like, it's nice to be nice to people. I think so too. It was really nice to be, you know, to be in a world where people show each other unexpected kindness. I like living in that world, especially in this city, because this city so full of cranky people that there's like a little gesture of sweetness to another person, you know, man or woman is, I think a very, it's a very worthwhile pursuit. It makes you feel good as the, as the doer of that act, much, as much as it does the recipient of that act. Yeah. I love it. I love it. Let's bring back men standing up for us, right? That's nice. It's one of the best parts of being a man, I think. I enjoy it. I think there's something very, very fulfilling as a man about sort of showing up with, you know, masculine energy, with with decisiveness, with, you know, with clear headedness, with an even temper, with a, with a very like a strong, what I would call like a strong masculine frame. I think that it's good for other men, it's good for women, it's good for young men to see an older man modeling that behavior. Yeah. It's good for a young woman to see a man modeling that behavior, so it's called younger men to a standard. Totally. You know, 100% agree with you. They say all their exes are crazy. What is a huge red flag? I would ghost on that one. Right? Yeah, because, you know, look, the trend they all have in common is you dated them. Yeah. So if you have awful picking skills, that's something worth noting, but it's, it's any time, you know, I tell people's story for a living in a courtroom. Yeah. And when you tell people's story, you have to hear their story from them first. And what I will tell you is any time someone tells you the story of their life or their relationship and they're the hero of the story. Be skeptical. Yeah. Like the most honest versions, if you say to me, you know, Jim, tell me the story of you as a parent. I'm going to tell you stories of, yeah, I'd got this right and then I kind of could have done this better. If you ask me stories about past relationships, I will not be the hero of the story 100% of the time. I will say, you know, here's what I did right. And here's the things I kind of screwed up and where I could have done better. And I think when someone tells you the story of their life or their relationship and they're consistently the hero of the story and the other person is the villain, that tells me something about their perception of themselves and other people and how they relate to the world. And that for me would be a huge red flag if somebody is just always the hero and the other person is always the villain. I think so too. Yeah. I totally agree. Um, okay, they refuse to post you on social media. So that would depend for me. I hate to be so nuanced in my answers, but no, I love it. As I discussed with your sister, I am a Libra. Um, we're very scales, we're very balanced. Yeah. Um, I, I will say if, if you, if it has importance to you, that you be on my social media and I refuse, that's different. Okay. And if you are a very private person and I'm not just forcing you into that spotlight, like I've had relationships where I was very public about it and I've had relationships where the, the person I was with did not want to be in the spotlight. Yeah. And so I think there is a version of that where you're trying to protect this person from public scrutiny, especially if you're, I represent a lot of celebrities and athletes and artists and musicians and a lot of them, like, you know, the person they're dating gets subject to a tremendous amount of scrutiny. Totally. And they don't really like that, you know, like, like the third most Googled thing about me is James Sexton girlfriend or James Sexton ex-wife. Yeah. And, and my ex-wife is a very private person. She's not a public figure. She met when we were in college. She's been remarried for 15 years and she likes kind of having a private life. Yeah. And so I've been very respectful of her privacy and not name checked her and the media and things like that. I, I think it's really about again, like does this person want to be, if a person says, Hey, I want you to be proud of our relationship, I want you to like, then I think it's different because you refusing to do that unless there's a reason behind it, you know, where, you know, I know I have clients who are, you know, they have controversial opinions. People have strong opinions about them. So they might be wanting to protect this person from danger and scrutiny. But sometimes, yeah, sometimes it's a way of hedging and kind of, you know, being secretive. Yeah. Secrets, there are good reasons for secrets and there are nefarious reasons for secrets. And I think you, I think you have to call it out. I think you have to be able to be comfortable with your partner saying, Hey, what is that? Yeah, it's going on there, right? I think so too. And if you're not comfortable, you have to ask why, right? Yeah. Why aren't you comfortable? Yeah. But I don't think it's a, I, I will tell you as someone who, you know, watches people break up for a living. I have a lot of people in my office who, you know, the week before they were like, hashtag best husband ever, like they're very public about their relationship. And meanwhile, you know, they're admiring, you're all admiring the drapes in a house where no one lives. Like it's not, it's not a real thing. You know, like I, I, I have clients who have very public relationships that have completely imploded and they just haven't got around to like correcting the record yet. So we're watching everyone's greatest hits in living our gag real. Like it's not, it's not really healthy. It's not, it's insanity. We're comparing ourselves to a curated version of people's relationships. And it's, it's like, it's like comparing your looks to someone who's got a filter on. That's a great way to put it. That's not fair. I love that. That is a great way to put it. Well, let me ask you this. So today, we're going to be talking about, you know, can you spot a divorce while dating, right? And someone that's really great to date, but maybe not good to marry, you know? Yeah, it's, it's good you make that distinction because I think, you know, just because you can cook doesn't mean you can farm, you know, like they both have to do with food, but they're totally different things. Like what makes a good girlfriend a good boyfriend might not make a good husband or a good wife? It might not make a good person to live a person you date and a person you live with. It might be very different. I think so too. What's one red flag that you've noticed, especially professionally, because you watch, like you said, relationships call apart for a living? What's one red flag during dating that almost always gets worse after marriage? Oh boy, that's a great question. So I first, I would put it into two broad categories. One is, And they're going to sound like a contradiction. One is the belief that if we move in together or we get married or we get in a very serious relationship that it'll preserve this thing and then it'll never change. Like that's a total fallacy. Like life's going to make you change. Like your body's going to change, your circumstances are going to change. Like the world changes, the world is turning. Like you can't stand still on a moving train. So like things are changing and you're going to change. So you have to be prepared that like being in a relationship, being married, cohabitating, it is not going to keep it in the pristine, perfect state that it's not like putting plastic on your couch, you know, or like a case on your phone, you know. But like putting a case on your phone, it changes the way you use it, too. Like it changes the look of it. So like all of these layers we put on to protect a relationship from changing, actually change it in some ways. The other big mistake people make is thinking, oh, that this person will definitely change. Like, oh, they drink a lot now, but if we like move in together, they won't anymore. Like they have a wandering eye, but if we move in together, we get married or we get engaged, then they won't anymore. That's not a great idea either. Like looking at a partner as like a fixer-upper is not a great way to go about things. Like so some things are going to change, some things are going to stay the same. You have to be prepared for both of those. So I think those are some red flags. It's thinking too heavily that this is never going to change or it's definitely going to change in ways that I want it to change. Those are both big red flags and I would say in terms of other, like communication is like everything. I mean, so much of our relationship is a function of how we communicate with ourselves and how we communicate with the other person. And those are two distinct pursuits, maybe really good at one and bad at the other. Like, but knowing what you want and then knowing how to say it out loud to the other person are two separate and equally important skills. And I think most relationship turbulence is a function of those two problems that you don't know what you want or you're not being honest with yourself about what you want. And you don't know how to express it to the other person. Totally. So I think someone who lacks an emotional vocabulary, lacks communication skills with themselves about what am I feeling right now? Like I feel sad. Am I sad or am I angry? Or I feel angry, am I angry or am I sad? Am I disappointed? What am I actually feeling right now? That's a skill. Yeah. It's a teachable skill. I think it's a practicable skill, right? I think you have to get some practice at it. But I think if you have that skill, that's a real plus. If you don't have it, it's a big red flag. Totally. I agree with you. Let me ask you, how does someone decipher the difference between someone who might be great to date versus great to Mary? Well, it's going to sound unromantic to say it, but I don't think it has to be. I think you have to look at it like a job interview, a job description. If you were hiring someone for the role of being your boyfriend or being your girlfriend, what would be in the job description? What is it you need from them? And what is it you're willing to exchange for that? What are you giving and what are you looking to receive? I think a relationship is an economy. And I know that might sound unromantic, but it's not meant to. An economy is any exchange of value. So how many apples is worth apples? That's easy. One apple is worth one apple. How many apples is worth a pineapple? OK, well, now we have an economy because a pineapple is bigger, it's harder to find. There's fewer places that grow it. So how many maybe four apples equals one pineapple? I don't know. We'd have to figure that out. And the economy depends on where you are. If you're someplace where there's lots of apples. And not a lot of pineapples. The pineapple might be worth more. But if you're in Hawaii and there's lots of pineapples, maybe apples are more scarce. So an economy is an exchange of value. If I bring to the relationship, I'm a great provider, I'm a great protector, I'm going to pay all the bills. I'm going to make sure that there's stability and security in our home. You are going to be the warmth and sweetness at the end of the day for me. Like the thing that I'm walking through fire to just get to where I can have that moment of calm and peace. Yeah. One of those takes like 12 to 14 hours a day to do, and the other one takes like an hour. But I would argue that they're equally important. Yeah. That they're equally valuable. They're equally hard to find. They're equally hard to remember why you're doing what you're doing sometimes. So I don't think anyone should be afraid to have a conversation about, hey, here's what I love about you. Like here's what you do that makes me want to be in this relationship. There's like, it's your warmth, it's your kindness, it's the gestures you get. Like those are a price beyond pearls. Like I can't put a numeric value on those. Yeah, I can put a numeric value on paying the rent and paying the car payment. But again, like, can you put a numeric value on stability, consistency, reliability? Like most of the things we love about someone, like it's really easy to go, oh women just, like want a guy who makes a lot of money. Or like guys really want a woman who's like super, like, you know, like has a great body. Yeah. Well, that maybe some way is true. But is it the thing or is it the thing under the thing? Because like the thing under the thing is what's a guy who's got money and success? Well, that's a guy who's got his act together. That's a guy who can like handle things, right? Because he probably wouldn't be successful if he couldn't handle things. And that maybe what a woman's really looking for is it's not the money. It's what the money symbolizes. By the way, someone who's fit, is it really that like, you see a person enough times naked, like they just kind of look like they look after a while, right? Like it's the truth. And so what it really is about is this is a person who has discipline. This is a person who trades what they want now for what they want most. Yeah. Like they may want chocolate cake, just like all of us do. But they might go, you know what? I want vibrant good health and to like feel fit and look good in my clothes more than I want that piece of chocolate cake. So you want someone to trade what they want most, right? For like they want what they want most more than what they want right now. That's a good relationship sign. So I would say that looking for a person who, you know, knows what they want, knows who they are and isn't afraid to be able to talk about the job description. I think that's what you want. And knowing the difference between what you want a boyfriend and what you want in a husband or what you want in a girlfriend, what you want in a wife. Right. Because there's things you're going to be a little bit more willing to accept, right? If you're just dating someone about the intent to marry them, right? Right. And not a long enough timeline. I mean, yeah. Look, marriage is kind of crazy in some ways. Like it's, you're signing up this person for a bunch of roles. Yeah. Like vacation partner, roommate, sex partner, friend, confident, parent potentially, pet parent, like those are a whole lot of categories. And if someone was good at all of those things, like that's kind of impressive, right? Like, like when I hire someone for a job in my office, I'm not like, by the way, are you good at every possible job? Like, no, not necessarily. Like I don't, and by the way, like, I don't know that I expect that. Right. Like if I went into an amazing sushi restaurant, I said, hey, do you guys make burritos? Like that would be kind of unfair. Like no, we make sushi. That's what we do here. We don't make Mexican food. Right. Right. Well, so if I went, well, no, I only want to go to a restaurant that serves the best of every possible cuisine. Like well, you're going to be looking for a restaurant for a really long time. So you've got to figure out like what is most important to me? And how is this person at that skill set? And by the way, like if you were to look at it like a car, the car you would want in your 20s and the car you would want in your 50s and in your 80s is going to be very different. In your 20s, you might be like, I want a Ferrari, I want a Maserati. In your 40s, 50s, you might be like, I kind of want to BMW or Mercedes or a Volvo, you know? And when you're in your 80s, you're going to be like, I want a Subaru outback or I want like, it's easy to get into and out of and have some room for groceries. Okay. So when you get married, you're picking your car for the rest of your life. And you're saying, this is the one car. So you sign up for a Ferrari when you need to put a car seat in the back of it, it's not going to work for you. Right. Like, I think you have to think about, who is this person? What do they have the potential to grow into being, you know, like do they, do they want to stay a Ferrari forever? Because if they do, that's okay. But I might not want someone who's like, I might want someone who's fun and exciting when they're in their 20s or their 30s, but then he's going to maybe settle down as we get a little bit older and, you know, your desires and needs and wants and motivations will change over time. So I think having someone who can have that conversation with themselves and with you, I think, is the key. Yeah. So let me see this. As a divorce attorney, what do you think destroys marriages the most? Is it infidelity? Is it money? Is it lack of sex? Or is it something else altogether? I think it's what's underneath the things you just listed. Okay. Like everybody wants me to say, oh, it's cheating or it's money or it's, but it's, it's really the thing under those things, which is loss of connection. Like I, you know, no single raindrops responsible for the flood, but the flood is just a bunch of raindrops. And so I think people who are happy don't cheat. Yeah. Like people cheat because there's disconnection. Now that doesn't mean it's the other person's fault that there's disconnection, might be your own fault that you've disconnected from this person. But I think the thing under the thing is always what's most important. And so to me, the biggest problem in relationship is disconnection because you, there are 8 billion people in the world, and you picked this person and said, "That's going to be my [BLANK_AUDIO] person, whether it's my girlfriend, my cohabitant, my wife, whatever, like you pick this person. And then, something changes, like something changes. And instead of doing what we should do when something changes, which is say, hey, did you notice something changed? It's not a complaint, I'm just noticing it. Do we need to talk about it? Is it a good thing? Is it a bad thing? Like, why is it? Because we all have a baseline. Like when you start dating someone, there's a certain amount of sex you're having. There's a certain amount of times you tell that person their handsome or their beautiful. There's a certain amount of time you hold their hand. Like, and as things change, I'm not suggesting that like five years into a relationship, you should have that same like electric feeling you did when you were first with that person. You'd never get anything done. Like if those early days feelings of like this person brushes up next to you and you're like, oh my god, I could feel that in the back of my neck. Like if it was like that 10 years into a relationship, it would be shocking to me, right? Right. And by the way, there's something kind of lovely about settling into like a feeling of like, oh, we're not as like wildly, but like we're deeply connected now. We get each other. We know what you're like. That's beautiful. It's lovely. But acknowledging that things are changing when it happens is good because sometimes it might just be, yeah, like right now I'm super stressed or oh, right now I've got this going on and that's why we're, oh, I didn't notice. Like I didn't notice that that changed. Like and it might be worth just pointing out or it might be okay to say, yeah, that changed because I'm just not as into that as I used to be. Okay. Is that okay? Or is that a deal breaker now? Is that something we're going to miss about each other? Like I think we avoid conflict, little conflict. And then we cause giant conflicts because of it because resentment start to build up. And when my sons were in their teens and they were first starting to like date. I remember saying to one of them, because he was dating a girl in that way. You date when you're like 15, 16 and he was like, yeah, she's mad at me. And I was like, what happened? And he said, well, I'm getting together with Chris and we were going to play World of Warcraft. And like, she was like, oh, I thought we were going to hang out and I was like, well, did you have plans with her? And he's like, no, I'd never like made plans with her. And I was like, well, when did you make the plans with Chris? He's like, like days ago. And I was like, okay. I was like, so you're going to disappoint her a little. Like that's okay. Yeah. And tell her that. She's disappointing you. And I think it's awesome that like you really want to spend time with me and I really want to spend time with you. And I'm excited that we're going to do that this weekend. But I made plans with Chris and I'm really excited to play World of Warcraft with them. And you know, like, I know that you have friends and you're going to want to spend time with them from time to time. And I'm going to miss you when you're doing that. But like I said, don't be afraid to disappoint a woman a little so that you don't build resentment between the two of you because one of two things going to happen now. If you don't disappoint her a little and you okay, I'm going to cancel with Chris. You're going to resent her. She might start to lose respect for you because you're so easy to manipulate in some ways. Like it might be better to just call this out and say, hey, I'm going to disappoint you a little and that's okay. I'm still going to be here. I'm not like I can carry the weight of your disappointment from time to time. And I hope you can carry the weight of mine from time to time because we're not always going to show up perfectly in this relationship and that's okay. Like I can love you and still be a little mad at you or a little resentful of you as long as we find a way through it. Yeah. But you know what? That's a good point. I feel like you were talking about earlier, you know, social media where you'll have someone come to you and they're getting divorced, but a week ago, they were talking about their spouse being like the best person on earth. And I feel like that's a lot of it too as we see so much of like people's relationships online, right? And we're getting like a false perception of what's actually going on. Do you think that there is like when you have clients coming to you more times than not are there people who are like the ones that are bragging about their spouse online are the ones getting divorced and I have found that like empty barrels make the most noise. Like the more that someone is trying to convince you that they're wealthy, the less wealth they probably have. Like I represent some ultra wealthy people here in New York, I represent, I have a client who's worth $8 billion, like I represent people in finance, a lot of them. And the wealthiest clients I have, like wealth whispers, like it doesn't, they're not the ones decked out in labels, they're not the ones driving $300,000 cars, like they're pretty chill because they don't have to flex that, you know? Like the toughest guys I know don't have to like walk around telling everyone how tough they are. Yeah. Like the people that are constantly trying to flex their relationship on you, my feeling is always who are you doing it, who are you trying to convince? Like if you're happy, go be happy. Like you don't have to film it. Go be happy. Like it's totally okay. Totally okay. Yes. You know? And again, does that, is there something lovely about like wanting to, you know, share some of your joy with the people in your life? I think it's lovely. When I see, you know, one of my friends post like, "Hey, happy birthday to my wife, you're the glue of the family, you're the best," like, "Oh my God, it's a cramp, I have a buddy Eddie who's out in LA, who's a Jiu-Jitsu guy and a sound tech and a brilliant," and he's been married for, I gotta be over 20 years at this point, he's wild about his wife. They got a bunch of kids, they got dogs, they got the whole thing, but he posts about her. But again, it's not every three seconds, it's like every month or so there's like some picture of her like a date night and it's a special occasion and it's just a reminder to the world, "Hey, this is my person. Like this is my person and I want to celebrate her and I'm proud of her and she's beautiful to me and I want to share my joy and pride in her with the world." I think there's something lovely about that, but the constant daily, you know, like even a person who every day has to post their workout or every day has to post what they're eating unless that's like what you do for a living as a food influencer or a gym influencer. I just don't see the point, you know, just shut the fuck out and live your life. 100%. 100%. Do you think that a relationship or a marriage could survive on chemistry alone? Like two people can, chemistry and connection be enough, whereas like compatibility comes into play. You know, like, do people have to have the same religious backgrounds, political backgrounds? I don't think you have to have those political background, religious backgrounds. I don't think, I think that those add some value, I think that, you know, being in a relationship with someone who shared your faith growing up, you have a common vocabulary. You know, if people have had a similar cultural experience, you know, it's nice to, you grew up maybe with some of the same foods or traditions, there's something lovely about sharing with another person. So I think there's value in that. Do I think you have to have that to be happy? I don't. I think that there's something lovely about dating someone who has a totally different background than you, and you get to like dip your toe in the pool of this person's life, you know, and get to experience the traditions of the culture you weren't raised in, and like you get sort of honorary membership in that. I think there's something really fun about that. So I think it really depends on how you enjoy a relationship. I think some people really love similarity and having someone who gets them in that way. And some people love like the novel nature of doing something different. I don't think there's a one-size-fits-all approach to that. But I do think that there is real value in knowing what's really important to you and being able to say it to a prospective partner, because I think some people, like their faith, is a cornerstone of their life, or their culture is a cornerstone of their identity. And I think if it is, it's okay to say that up front to someone and to, you know, prefer the things you prefer. Like, we feel what we feel. Yeah. Like, sheer power of will is not going to make you feel something different. Like, you can change your thoughts or your logic behind things, but your feelings or your feelings. You don't want to feel a particular way, but you do. So I think it's okay to, like, say, hey, this is a feeling. I always say, like, feelings are, like, little kids. You can't let them drive, but you can't shove them in the trunk either. Like, you kind of have to find this balance where you let them have voice, but you don't let them run the show. Because we are, Shup and Hower said, you know, people think that humans are thinking machines that sometimes feel, but actually we're feeling machines that sometimes think. And I really believe that to be true. I think we're more ruled by our emotions than we want to acknowledge. And that's okay, as long as we're aware of it. Yeah. And I think in relationship, you know, love is in some ways a delusion brought on by an adequate lighting. Yeah. Like, I think you're, you know, you just are, like, caught up in this thing and it feels so good and exciting and wonderful that you make some bad decisions, probably. You don't, you let your logic go out the window and that's part of the fun of it. It's running your brain off and having fun. But again, this is the difference between dating and tying your destiny to another person. Yeah. That's true. Do you think that age plays a role in divorce, like I see quotes on Instagram that like if I got married in my 20s, you know, I'm in my 30s and single, I statistically avoided my first divorce. Yeah. Do you think people who stay single longer have a smaller chance of being divorced? Well, there is actually a correlation up to a certain point. So if you look at the data that's out there on this, people who marry very young actually have better outcomes in terms of not divorcing than people who marry past a certain age. But it gets tricky when you look at some of the other cohorts. because college educated or higher have a lower divorce rate than people who aren't. Certain socioeconomic levels have a better outcome. All the people that talk about how marriage is really important and sustaining marriage and showing up marriage is important. They actually should be pushing for student loan forgiveness or more accessible education and lower income inequality and people being able to make a living wage and have what they need resource-wise to be able to like live a comfortable life because that is actually a better predictor of long-term marital success. Not having massive financial stress and having actually more education is one of the best things you can do to shore up the value of a marriage staying together. So I think that there's a lot we could do to shore up marriage. I don't know that what age you do it at is most important because there are people who I do a lot of pre-nubs and I just was doing a pre-nub consultation today for a young man who is a very successful businessman now and he started a tech startup and he spent most of his 20s with his head down just doing his work. Yeah. Like just really hyper focused. Now that can go one of two ways. Like yeah he's got a lot of really great things that he built but he's not done a lot of living. Like he hasn't run around and dated a bunch of people like he's kind of had his head down and been in the office most of the time and now he met someone he really likes them they really like him. He's talking about getting married. He hasn't really spent a lot of time out in the world yet so he may turn around some day and go well come on like I got a lot of living to do here you know. But again I know some people that same age but they've run around and had themselves a hell of a time and some of them got it out of their system and now they're ready to settle down and some of them might think they're ready to settle down but now they've tasted how fun it is to run around and be chaotic and have tons of diversity or relationship. So I just don't think we we want so bad for there to be like a formula. Right. And like oh if it's this age difference it's good but if it's beyond that it's bad or if it's like we want it to be algebra. It's not like this isn't baking it's cooking. Like baking is tablespoon of this little bit of baking so if you put too much or too little you screwed the whole thing up and it's not going to work. Cooking is like try it taste it no it needs a little more of this so you can't you can put salt in but you can't take it out like you have to feed like you got to play with it though you got to get a little dirty you got to like you know you can't follow a strict strict recipe you know baking is a very strict recipe like this isn't science it's art it's a little bit of magic it's a little bit of vibe it's a little bit of gut instinct it's your head it's your heart it's your gut it's like the combination the chorus of all of that yeah I know it's perfectly normal and human to like want the formula and I think that's you know part of the human desire to control things you know I have a friend Mark who's a therapist who's a really cool and insightful guy and he always says to me whenever I'm talking about something that's stressing me out he always says you know Jim relax nothing's under control it's true and it really is like it really is like the sooner that we realize like we don't have as much control as we think we have and we're kind of we're kind of riding some of these waves I think the happier will be I wish I had like a magic formula I could tell people like this age gap and this faith versus this and live together or don't live together and that's the magic stuff doesn't work that way you do what I do for a living you see people that live together you see people that didn't live together you see people the same faith different faith big age gap no age gap there's no rhyme or reasons no rhyme or reason yeah what advice do you have for people who are over 30 and they're single and they want to be married I think it's good that you know what you want I think knowing what you want is is one of the first steps to potentially getting it but I would say that you know if you have one I focused on the destination you only have one with which to see the way like I think you have to you have to walk the path like I think you have to I think it's really important to know what you want but I also think it's really important to not hyper fixate on the goal because I think by just existing in the world and living you're like your life is happening right now it's not something that you're walking towards it's something you're in like like you're not you're not stuck in traffic you are traffic yeah like you are you're part of the traffic like your car is someone else's car in front of them that's annoying them like in the car that's in front of you there was annoyed as you are like you're not in traffic you are traffic so you are living your life right now yeah so wanting to find connection to another person I think it's a very normal wonderful thing I think some people go okay I wanted to start taking this more seriously that's great that's a great thing to do but it's it's not like okay now I'm going to hyper fixate on this thing because I think sometimes that's actually counterproductive I think that being so fixated on the outcome takes away from you being focused on the process but again not in any way focusing is not good I think you should start asking people should reach a point where they start asking them the question of do I want to just date and have fun or do I really want to find something lasting and I think finding something lasting requires a certain mindset and focus I think so too I do too and like just being intentional right yeah right I most of all with yourself yes like being honest with yourself even when it's like a little disappointing yeah you know because you might like meet a person that's like oh my god they're so fun like they're so fun like I've so much fun with them but they're not gonna be a serious person like this isn't a person I'm gonna be able to like this isn't a foundation I'm gonna be able to build something on and I want to build something yeah like and again that's what discipline is discipline is trading what I want now for what I want most yeah and I think the older you get the more you start to see that like I will say a defining characteristic of my 50s has been that I can see the tie between what I do on Monday and how I feel on Friday and I didn't see that in my 20s yeah because you're just so first of all your prefrontal cortex isn't fully developed and second you're just all gas no breaks and that's like a beautiful thing about youth is that you just are all gas no breaks and you're just like living and out there but I do think there comes a time where you want to start going okay like yeah that feels really good yeah but like what do I really want what do I want most and if what you want most is like deep depth of connection with another person you're gonna trade novelty yeah you have to like you have to there's something wonderful about novelty there's something wonderful about those early days of connection with another person like there just is there's something really magical about that but you know there's also something really magical about deep connection to another person in a real profound way and you can't have novelty and that kind of depth of connection you've got to pick one or the other and I do think there is ultimately real value in depth of connection but you have to be willing to trade certain things for it like I get flack for saying this sometimes but like I believe in the form of monogamy where I have sex with as many people as I want to and ideally that's one like I'm because if we're in a relationship that's a good one and but if we're in a relationship yeah I love that and you say to me you know Jim I met a guy today I really want to have sex with but I you know we made this rule that we're not gonna have sex with other people so I didn't okay like don't do me any favors like does it make me feel better if you're like I really want to have sex with a bunch of people but I've you know I've committed to this relationship so I'm not gonna do it like that okay that doesn't feel good yeah like but if if you take the attitude of like yeah like I don't eat when I'm not hungry like when I'm satisfied I don't want you more to eat like if you made murder legal I wouldn't go kill people yeah like if the only thing that's preventing you from killing people is that you're afraid you're gonna get in trouble brother you got some thinking to do like like I don't kill people because I don't want to like I believe other sentient beings have the right to exist and I believe in their autonomy and agency and I I don't want to live in a world where people just kill each other randomly like so it's not about the rule it's about what's under the rule so a form of monogamy where it's like hey you and I have agreed we're gonna not share this aspect of self look we're not gonna share our bodies with other people yeah okay well then you owe me something and I owe you something right like like I'll even take take the sexual element out of it I have routinely said in relationship if you're gonna rob me of my solitude you owe me companionship so that works like I like being alone so if I'm gonna give up the joy I feel being alone to be with you you owe me companionship that's at least as enjoyable as my solitude I think that's fair like if you want me to not have sex with other people okay then we have to find a way to satisfy each other when it comes to sex because you're asking me to give like if if I have to if one woman Has to be such that I would give up all the other ones and if one man is to be so satisfying to you that you were to give up all the other ones I think that man owes you something that seems fair to me. I think so right and I think everything comes with a cost at the end of the day right and that's not necessarily a bad thing But but again saying that everything comes with a cost is really another way of saying that all relationships are an economy Yeah, and so that's okay like it's but the worst thing is if we just why can't we say it out loud right like why can't we say out loud By the way, it could be really fun to say it out loud. I know right isn't it fun to say to another person you know what I like about you You know what I enjoy about you like you can do it all day long we can do it right now you know what I'm enjoying about this interview You're very engaged. You're very focused. You ask interesting questions. You have something to say okay. Isn't that fun? Isn't it fun to share with each other like hey, what are you worried about in this and everyone I'm worried I'm talking too much I'm worried I'm not saying or I'm worried that I'm not going to get to the questions enough because the answers are going long Like it's okay like it's okay for us to just say that out loud to each other And don't we feel a little closer when we like share like yeah, here's what I think we're doing right and here's what I think we're kind of screwing up Or here's what we could do better like why not make a game of it why not make it something that we do early and often in relationship And build it and we have all these devices people have that remind you to drink water and when to stand and when to sit and when to you know do this Okay, we can't build Five ten minutes a day into our routine where we like remind this other person hey I still really think you're so pretty. I think you're so handsome. You make me really happy You know that here's something I think of when I think of you here's I heard this song it made me think of you today Like I said like what does it take what is it crossed to do that nothing nothing takes ten seconds to send someone a text and say I was thinking of you You know I'm so like I you know you're so handsome. Who would I want to hear that right? Who didn't want to hear that? Who does it not feel good to hear that? Even with your friends any relationship in your life what's what is it called I had one of my dear friends from college Yeah today just sent me a text out of the blue saying you know I'm just so glad for all the value you brought to my life And I just wanted to tell you that like I was standing outside of a restaurant waiting to meet a colleague of mine for lunch And I got that text that I wrote it back and I was like man anything I've ever done that added value to your life Was like a small repayment for all the value you brought to my life like it was like a five-second exchange between two friends That don't see each other but every couple of years and we knew each other 30 something years ago at this point but like what a lovely moment to have with another person it cost us nothing It cost us five seconds of our time like and you can't do that to this person that you signed on that they're your person Like I would do that for a stranger on the street takes five seconds doesn't cost anything why wouldn't I do it for anybody I could do it for Why would the my person I'm not going to do it for them? Yeah I agree with you and it's sad that we're talking about it like it's a rare thing now you know what I mean It is because there's no reward built into it like there's no The algorithm is trying to convince all of us that like you don't owe him that you don't owe her that you're right We don't owe each other anything like we're born alone we die alone like we don't owe each other anything So you don't have to be in a relationship you don't have to be with each other but you chose to be So if you chose to be why wouldn't you want to like yeah I owe this person a little they owe me a little like let's let's play in that space together And like figure out what we mean to each other you know and I don't know to me if you're going to hyper fixate on like I don't owe this person whatever Okay then yeah don't owe them anything so do you yeah right I agree with you do you think love is a choice because we're talking about choices I think love is a verb okay I think love is a feeling and I think love is a verb and those are two different things like that song by John mayor No there's another one there's another one I know I know there's a couple songs yeah the John mayor has a song called love is a verb Because I say that all the time that love is a verb people like do you mean the song and I'm like he's a Libra he's a Libra I'm a fan too I think I think love is a series of actions like it's treating someone with love but it's also an emotion I think the emotion part is easier than the verb part yeah treating someone with love requires a certain attention and it requires a certain action And I think that's the part that we sometimes screw up we also take for granted how much value we present to the other person See like you can you can look at another person's expectations of you as a burden or you can look at it as a gift like that you you mean something to this person You bring value to their life and I think when you parse it that way in your head like almost everything that happens to us happens in our head Isn't that crazy really it's like it's yeah like most of our life is spent in imagination Right like most of scenarios we create that we have exactly about never actually coming to pass Yeah, they're we're just paying like interest on worry that's not do you know like we're just and I I think it's very human that we do that We also even the past the way we remember it is so infused with storytelling As someone who tells people story for a living I can I can attest to this but I do think there is something really beautiful about acknowledging that you know Yeah, a lot of our fear is imagined a lot of our hopes are imagined a lot of our life is spent in fantasy But the danger of that is when you're in relationship are you comparing this person who you're in partnership with To your imagined perfect boyfriend or girlfriend or are you comparing them to real people Yeah, because I guarantee no one will be as good as your imaginary perfect boyfriend or girlfriend 100 they will always disappoint you like because you're imagined perfect boyfriend or girlfriend will always know the right thing to say And the right thing to do it exactly the right time that's why they're imaginary right like but real people are gonna disappoint you sometimes Real people are gonna miss the point or lose the plot sometimes and by the way I kind of want that Right because I miss the point sometimes I lose the plot sometimes and I want someone who's gonna be like yeah I'm a little angry at you right now. I love you. Yeah, but I'm a little angry. Yeah, I love you, but I'm a little disappointed right now And that's lovely like I want someone who's gonna love me at my worst. He's gonna love me at my best Yes, 100% I agree with you And I think it's good to have standards, but you also have to have human expectations Absolutely, and I think in dating we make a huge mistake by like putting spanks on our personality for too long It really is like like I get that you show up at your first date like ducked out and like I get it Like I don't think your first date should be at a swimming pool like I think it's okay to like your first date you want to put your best foot forward And maybe you're not gonna like tell this person all your insecurities and problems on the first date Yeah, but I don't think that like when you're in the talking phase or when you're in the early days Like that keeping that like like I said spanks on your personality for too long is good I think you have to start letting this person in to the shit you want to work on the stuff you're a little You know like yeah, I need to work on this or this is something I do that I don't love about myself Like and again, it doesn't have to be a therapy session, but I think infusing The artifice with realness the messiness is nice. Yeah, it's nice and by the way There's something kind of fun about sharing your messiness with another person. I think so too especially when they make you feel safe sharing it right? Yeah, and there's something fun about like kind of matching it like I got this. Oh, yeah I got that too or I don't have that but I have this and like oh, okay cool like I think the best you can hope for because you're not gonna find a person that doesn't have flaws and pathologies I think you want to find someone who has complimentary pathologies. Yes. Like you know, I'm a little too much of a planner She's a little too fly by the seat of her pants. Cool. Maybe you'll help me like calm down a minute and I'll help you kind of get it together Alan. Like isn't that nice? Like isn't it nice to have polarity with another person? But again, so much polarity. Yeah. That you're like totally different and like no you're a total mess and I'm a total neat freak That's gonna be a problem. Yeah, but like having a little polarity is fun. It's nice. It's the basis of attraction. I think so. I think so for sure. And you talk about how you work a lot with prenups. Yeah. You love a lot of like high net worth right divorces. Yeah. So what is one piece of advice you have for people who are married when it comes to finances? Like should people have joint bank accounts? Should they have separate bank accounts? What do you think? My personal belief. I mean, again, I don't like one size fits all answers. I think marriage and relationship is very, you know, the circumstances and the chemistry of the ecosystem of a family is unique to the circumstances. But if I have to make generalities because I do think there's some value to that. I think stereotypes can be a real time saver. I think that I like the idea of yours mine and ours. I think every relationship at its core is you, me, and we. Like every relationship. Yeah. And ideally, you were you, I'm me, and then there's a we and the we gets bigger and bigger and bigger. But you don't want it to get so big that it eats the you and the me because like the you is what I fell in love with and the me is what you fell in love with. So if it all goes away and becomes the we it's like now we I took away the your favorite person and my favorite person. So finances, I think it's the same thing. Like having everything totally amashed to me feels weird. Like if I want to buy you a birthday gift, I don't want you to see how much it costs and I don't want you to see. Like I want there to be some privacy between us. - Yes. - I'm not like, you know, leave the bathroom door open guy. Like I may, I like there to be a little mystery. I like there to be a little between the two of us. There's some things that are just privately yours and that are privately mine. But having so much separateness that there's no shared space, there's no shared investment. I don't think that's healthy either. I think you have to find the balance that works for your relationship. What I like about yours mine in hours is maybe there's a shared account where we pay like the family bills, our shared expenses, you know, the things that we're saving for together. But maybe we have a little bit of separateness that in God forbid something goes wrong with the two of us. We both have some access to funds. But also, even on a positive level that we can surprise each other and you know, buy each other presents or, you know, like make our own autonomous financial decisions from time to time. Like if I want to buy some dumb thing, I can go do that if you want to buy some dumb thing. Like I don't, I might not want to know what your shoes go. - Yeah. - You know, it might, it might sticker shop me 'cause mine aren't that expensive, you know? But I think there's value in each of you having again, the you, the me and the way. - Yeah, I think that's a good answer. Do you think everyone should have a prenup despite whatever they're not worth this? - Well, everyone has a prenup. It's either one that's written by the government and can be changed by the government without your permission. Or it's one that you and the person that you like more than the other eight billion options wrote together. Which do you think is better? Like have you, you've been to the DMV? I've been to the DMV. You walk into the DMV and go, "Oh, these people are great at everything." They should be in charge of my relationship. Like I don't feel that way. Like I walk in almost any government agency and I go, "What in God's name did they put these people in charge of?" So I think that you have to remember that every marriage has a prenup. It's just one that was written by the government and can be changed by the government without notice to you. That to me is kind of scary. Like whatever your political affiliation at some point in the last 20 years, you've looked at the government and went, "Oh, I don't like these people." Like at some point, like my Republican friends didn't like Biden, my Democrat friends don't like Trump. Like okay, so at some point, you've looked at the government and said, "Yeah, I don't like these persons." Okay, so why would you let them write the relationship rules? Why would you let them decide? Why can't the two of you decide? What's uncomfortable to talk about it? Okay, you're gonna marry a person, you can't have uncomfortable conversations with. Yeah. That's not a great sign. Like that's not a great sign. Like have the uncomfortable conversation. What, by the way, when should you have those conversations? Like you want to learn how to fight when you're in a fight? Yeah. That's the worst time to learn how to fight. The best time to learn how to fight, even how to argue. Like if we're in a relationship and I say to you, "Hey babe, listen, we're gonna get in a fight someday." Yeah. We're gonna get in an argument. I'd probably be my fault. I'm gonna say something stupid. I say stupid stuff all the time. So it might happen. When we do, are you the kind of person that you need a minute, like I need to let you cool off? Or are you the kind of person that's like, "No, no, no, no, we can't go to bed angry." Like we gotta sort this out tonight. 'Cause like let's have that conversation now. Let's not have it when we're in a fight. Yeah. So prenup is just that. We're just saying, "Hey listen, you want to feel safe in this relationship, I do too." I am willing to take some risk in this relationship. I hope you are too. Yeah. Can we now, while we love each other and have an abundance of optimism? Could we make those rules now? Because I have to tell you like, I don't want you to be in a relationship with me because you're afraid to get divorced. I want you to be in a relationship with me because I had value to your life and that every day you look at me and go, this person, my life is better for the fact that I'm with them. I don't want it to be that it's like, well, if we break up, it's gonna be like, I don't have to get all new stuff. Like that is not a good reason to stay with somebody. Like, rules are a great servant in a terrible master's as far as I'm concerned. Whether it's the rules of monogamy, whether it's the financial rules of a marriage, write your own rules. Like, one size does not fit all. The two of you should have a conversation about what's important, what you're scared of. What is a prenup but a conversation about what I'm scared of? I'm scared that you're gonna take all my money. I'm scared you're gonna control the money and leave me with nothing. Okay, let's talk about that. If I love you and I wanna spend the rest of my life with you, I should be able to carry the weight of your fear, right? And you should be able to carry the weight of mine and we should be able to talk to each other about that. That's a beautiful, beautiful thing to love a person enough, whether they're your family member, whether they're your lover, whatever, they're your child, anybody, or your friend, to be able to like, tell me what you're scared of and I'm gonna try to help you be less scared. Like, isn't that the point of love? Like, isn't the whole point of love like, holy shit, this is scary? - Yeah. - Can we hold each other's hand and maybe it'll be a little less scary? Like, that's, if that's the point of love, why wouldn't you have a prenup? - 100%. I think that's a great point though. It's either you're gonna write the prenup or someone else's for you, right? Yeah, what's the craziest thing you've seen in a prenup? - Crazy is prenup provision. I mean, I've talked about this before, people still find it hard to believe, but I did have a prenup where for every 10 pounds that the bride gained, she would lose $10,000 of alimony a month, yeah. - Wow. - And that was enforceable prenup provision that the court upheld, yeah. The judge actually said, this is a bullish provision, it's disgusting. I don't know why you married this person, but it's a binding and enforceable provision and it was a binding and enforceable provision. But I see where people put in, you know, in fidelity penalties, people wanna put in things about how often they have to have sex and if there's penalties, if you don't have sex that many times, like people wanna, you know, people wanna put like, you know, bubble wrap around aspects of their relationship and they think that creating penalties is gonna accomplish that. It's kind of adorable that we think that, but it's kind of like, saying like, let's make drugs illegal. That'll stop people from using them. Like, okay, sure, that's, how's that working? Is it working well? Like, that's so funny. Let me ask you this, what's your most controversial piece of dating advice? My most controversial piece of dating advice is talk about prenups really early in a relationship like third date. - Ooh, yeah. - Okay. - Because I think it's an invitation to a conversation about what you're scared of and what you believe the economy of a relationship should be. So I think it's an interesting entry point. Chris Williamson asked me, when should you bring up a prenup and I said third date? And he was like, wow, that's a very specific answer, but that's my answer. I think, I think a controversial topic for me is I think you should bring up, how do you feel about prenups very early in a relationship? Because it tells you a lot about how this person views the economy of a relationship and what they're scared of. - Yeah. - So that would be my hot take. My other one would probably be, I think how you do anything is how you do everything. So I think my hot take would be that, like the most dangerous lies are not the lies other people tell us the most dangerous lies are the lies we tell ourselves. It's like get your story straight before you go out trying to solicit other people's stories. Like be honest with yourself about what do you actually want? 'Cause who we like to think we are and who we are is very different sometimes. So I think if you're getting serious about dating, meaning you're looking for something other than transient connection. Like you might want monogamy, you might want cohabitation, you might want marriage, you might want kids, you want something more serious. The first most important question is who am I really? Like who am I really? Not who do I wanna be, who do I aspire to be, who do I hope I am on Sunday night when Mondays coming around the corner and I'm gonna make new resolutions in different choices this week, who am I actually? Like on Thursday evening when the day has worn me down, who am I really at that moment? How strong is my will, how good is my focus? Because that's the thing if we're honest with ourselves about who we are. I think we have the best chance of finding like lasting connection to another person. Yeah, I think that's great advice though. Great advice. And we're kinda coming to a close here, so we're gonna end with a little rapid fire. Let's do it. All right, save yourself for marriage or sex on the first date. Wow, those are my two choices. - Raptify? - I think they both suck. I think sex on the first date's a terrible idea if you want there to be any seriousness of the relationship. I also think it's a complete waste because part of the fun is the progressive revelation. Like what happened with your generation and younger with bases? Like I'm 54. There were bases. - Right. - Like there was a delay in kissing someone, then you kissed them and there was just kissing for a while and then there was like okay, now we're gonna do some like over the close under the closed stuff. Like there were bases. - That are looking forward to something. - Yeah, like you only get to do something for the first time, one time. - I know. - Like why would you rush? Like why wouldn't you want to save her every more so? Like if you went to a restaurant, they brought out all the dishes at once and just you know where like here's the appetizers, here's the thing, here's dessert and you just had to eat it all at once. You'd be like the sucks. There's something really fun about what's next. Like what's coming, oh my God, that was so good. I wonder how this is gonna be. Like when I have the appetizers at a restaurant and they're really good, I'm like, oh my God, the meal's gonna be so good. Like if there's something exciting about that anticipation, Why would you rob yourself of that? - I agree. I agree. And I think there's like some dangerous two to hook up culture, but that's a whole different, right? - Totally. - We do a whole show on that. - Yeah, right, totally. Okay, do you open relationships of work? - I'm the wrong guy to ask, because all I see is when they catastrophically fail, 'cause I'm a divorce lawyer. - Right. - So people ask me all the time about ethical nonmenagamy, polyamory, different models of relationships. I see when it was a Hail Mary pass, 'cause the relationships just falling apart, and they're like, I don't know, let's sleep with other people, maybe that'll help. I see it when it catastrophically fails, but I have a friend who's an oncologist. If he called me and was like, dude, everybody has cancer, I'd be like, no, you're an oncologist, of course. Like you meet people who have cancer, like that's your job. Like I meet people who are divorcing. So that's what I think everybody's doing, but I'm sure that there are people that have non-conventional styles of sexual connection that are perfectly healthy. - Yeah. Okay, that's fair, it's a good answer. I like it, I like it, James. Thank you so much for coming today to tell everyone where they can follow you. - Well, you can follow me down the streets of Manhattan, 'cause that's where I'm walking most of the time, but if you wanna follow me on social media, I'm at NYC Divorce Lawyer on Instagram. You can find out more about my firm at nycdivorces.com, and I think I'm on TikTok at NYC Divorce Lawyer. - I love that, are you taking new clients? - I am, but I price out most people. I take a limited number of clients, and all of them have in common that they have a lot of money. - Oh my gosh, well, thank you so much for coming today and sharing your words of wisdom. - I really enjoyed it, I'm so glad we made it happen. - I know me too, so glad we made it happen. - The way you've not let the West Coast East coast things stand in our way. - We literally didn't let it happen. - I love it. - Distance wasn't an even a problem. - It was absolute pleasure. - Maybe long-distance relationships can work out, right? - We did, we did, look at that, it's perfect. - I love it, I love it, oh my god. Thank you so much for coming today, and thank you guys for watching, I'll see you next week. (upbeat music)