In Search Of Excellence - Divorce Lawyer Jim Sexton: Why Marriages Fail, Prenups, Sex, Monogamy & Divorce | E192

Episode Date: August 18, 2026

Divorce lawyer Jim Sexton has spent nearly 30 years watching marriages fall apart - and he knows the mistakes couples make long before they ever enter a courtroom.In Part 2 of my conversation with Jim Sexton, one of the country’s most experienced divorce attorneys, we go deep on marriage, divorce, prenups, monogamy, sexual compatibility, dating, choosing the right partner, divorce statistics, and what actually makes relationships last.Jim has represented executives, entrepreneurs, CEOs, athletes, celebrities, and high-net-worth families through some of the most difficult divorces imaginable. After decades on the front lines of family law - and after going through divorce himself - he has developed some fascinating and sometimes controversial views about love, marriage, sex, money, and relationships.We talk about why getting married may be one of the most legally significant decisions you’ll ever make, despite most people having almost no idea what they are legally agreeing to.Jim explains why the best divorce lawyer may actually be the lawyer who keeps you out of court, why spending $10,000 fighting over $5,000 makes no sense, and why divorce should eventually be approached more like a business transaction than an emotional battle.We discuss whether prenups are unromantic, whether they actually hold up in court, and why Jim argues that a thoughtfully constructed prenup can actually create greater emotional and financial safety in a marriage.Then we get into some of the most controversial research and observations surrounding sexual history, sexual satisfaction, monogamy, marriage success, and divorce.It’s a conversation about how to choose the right person, build a stronger relationship, understand what marriage actually means, and avoid mistakes that can cost you emotionally and financially for years.TIMESTAMPS00:00 — The legal reality of marriage almost nobody understands05:45 — Why a great divorce lawyer may actually keep you OUT of court12:53 — How to find a great divorce attorney without trusting Google rankings18:44 — The “Sopranos strategy” before divorce—and why Jim says it can backfire24:27 — Why Jim Sexton says every first date is basically a sales call29:59 — The fear that stops people from making the move they actually want34:20 — The 3 real reasons people get married41:30 — Who probably should NOT get married46:07 — “Everyone has a prenup” — Jim explains what most couples don't realize51:41 — How long should you date before getting married?59:38 — Do more sexual partners increase the likelihood of divorce?1:07:42 — Jim's controversial definition of successful monogamy1:20:11 — Why divorce rates rise dramatically after the first marriage1:31:12 — Do prenups actually work? What they can—and cannot—protectABOUT JIM SEXTONJim Sexton is a veteran matrimonial and divorce attorney with nearly three decades of experience handling complicated divorce, custody, financial, and family-law disputes.Throughout his career, Jim has represented high-net-worth individuals, entrepreneurs, CEOs, executives, athletes, and celebrities while developing a reputation as an experienced courtroom strategist and negotiator.ABOUT RANDALL KAPLANRandall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of the In Search of Excellence podcast.Through his Extreme Preparation™ methodology, Randall helps founders, executives, business owners, entrepreneurs, and ambitious professionals improve their strategy, communication, preparation, decision-making, and execution so they can achieve extraordinary results in business and life.WHAT DO YOU THINK?Should everyone get a prenup before getting married?How long should couples date before marriage?And what matters most to a successful long-term relationship: love, compatibility, communication, sexual chemistry, financial compatibility—or something else entirely?WANT TO WORK ONE-ON-ONE WITH ME?I privately coach a limited number of founders, executives, business owners, entrepreneurs, and other high achievers who want to elevate their careers, scale their businesses, make better decisions, and reach higher levels of success professionally and personally.If you're ready to change your life and achieve your goals, apply here:www.randallkaplan.comWATCH MY EXTREME PREPARATION™ TEDx TALKHow to Get Your Dream Job with Extreme Preparationhttps://www.youtube.com/watch?v=MIvlFpoLfgsLISTEN TO IN SEARCH OF EXCELLENCEApple Podcasts:https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310Spotify:https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6LFor more information:www.randallkaplan.comFOLLOW RANDALLInstagram: @randallkaplanLinkedIn: @randallkaplanTikTok: @randall_kaplanX / Twitter: https://x.com/RandallKaplanWebsite: www.randallkaplan.com1-on-1 Coaching: www.randallkaplan.comAbout Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.Coaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X

I'm going to not have sex with other people in exchange for exclusively having sex with you. I feel like there is an obligation there. And as unromantic as that may sound. I'm a big believer in love, but I don't believe in fairy tales. But when you go through a relationship with rose-colored glasses, all the red flags look like flags. If the man has money, signing a pre-up, isn't it treating like your future wife like a prostitute? If you just show up in your next marriage and you say, listen, I had a lot of resources when we met. So I want you to sign this pre-up.

It says that you get nothing. Don't marry that guy. My guest today has spent 25 years in the most intimate courtrooms in America, not criminal courts, not corporate boardrooms, but the room were two people who once chose and loved each other above everyone else on earth, sit on opposite sides of a table, divide their lives, and often end up hating each other. James Sexton is one of the country's top and most successful. testable divorce lawyers. He's handled over a thousand matrimonial cases, written two bestselling books.

If you're in my office, it's already too late, and how to stay in love and has become one of the most watched voices on the internet when it comes to love, relationships, and why they fall apart. Here's what makes him different. He's not just cynical. After 25 years of watching marriages, he is one of the greatest advocates you'll ever meet for love. He just happens to know exactly where it goes wrong, and today's going to share it with us. James, welcome to The Search of Excellence. Great to be here. Always good to see you. So I think it's great to be an expert at things before we get into it, especially my podcast. And divorce is a subject where, unfortunately, I am an expert.

I'm going through my second divorce right now. I was married to my first wife for about eight and a half years together for 11. I'm at the tail end of getting a divorce now, being with my soon-to-be ex-second wife for 12 and a half years, married for 11. So this is a topic I know extremely well, all areas of a divorce. Let's start with the beginning. what is a divorce lawyer and what does a divorce lawyer actually do? Gosh, a divorce lawyer is a combination of a lot of different things. I mean, at a fundamental level, what we do is we help people from a legal standpoint untie the

ties that occurred legally when two people decided to engage in the legal status of marriage, as opposed to the religious or spiritual aspect of the union that we refer to as marriage. Because I like to separate those two concepts because I think that marriage is, you know, both a legal framework and it's also a religious sacrament in some, you know, in some religions. It's also a spiritual connection that two people make. But really what a divorce lawyer's role is fundamentally is to assist with the legal dissolution of marriage to help you untie all the things that occurred legally when you got married. Getting married is the most legally significant thing a person can do other than dying. Dying, there's a lot of things that happen legally when a person

dies tied to surrogates law and a state law. But marriage is the most legally significant thing a person can do other than dying. But it's also something that very few people understand what happened when they got married legally. Like most people, like you buy a house, you get a lead paint disclosure, a HUD one form, all those kinds of things. You start a business. You get all kinds of disclosures and contracts. You get married. You didn't get a pamphlet. Like it's just such a legally significant thing. And no one explains to you. And most people only learn for the first time, happened legally when they got married when they're on the other end of it, when they're getting divorced. But that's the simple explanation of what divorce lawyers do. I see a divorce lawyer as a combination

of a, you know, a negotiator, a consigliary, an advisor, a quasi-therapist in some ways without a lot of training in mental health. We advise people during a really, really challenging moment in their life. I think the most rational thing a person could say to me when they were going through a divorce is I really shouldn't make any big decisions right now because I'm going through a divorce. And yet you have to make big decisions about your divorce while going through a divorce or you would just never get out of that cycle. So yeah, I mean, we're really kind of the front lines for a person in terms of there's a forward-facing aspect of the job, the one that you see at the negotiating table and in the courtroom. And then there's a non-forward facing part that's

really subject to attorney-client privilege where we're really behind closed doors having very pragmatic, practical, hopefully candid and blunt conversations with our client. Because as you've probably seen even firsthand, you can spend $10,000 arguing over a $5,000 bank account in a divorce. And there's just no reason to do that. And so one of the things a responsible divorce lawyer does, because divorce lawyers live and die by their reputations. There's a tremendous incentive to amplify conflict for a divorce lawyer because if we're, if we're successful in achieving our client's stated goals, we look, we look brilliant, even if we had nothing to do with it, you know, even if it was just the nature of the facts and the law. But if we lose, we still get paid. You know, unlike

personal injury lawyers who get, you know, a third of the recovery, you know, if they win and nothing if they lose. If I lose, I still get paid and I can go, ah, this judge, I can't believe they got it wrong. Anyway, here's my invoice. And so I take that. I take that. I take that. I'm a lot. I take, is a tremendous responsibility from the beginning to say to a client, you know, I'd rather you pay her than pay me. I would rather you put your children through college than mine. Right. So one of the things that's very interesting, I'm a former lawyer myself, as you know. I'm proud of you for getting over the fence and making something of yourself. I hated it. I hated law school like you. I did it as a means to an end. I want to make money. When I graduated law school 31 years ago, I went to Northwestern.

The starting salary was $70,000 a year. I was rich. There was nothing I couldn't do. You did better than me. My starting salary as a lawyer was $50,000 a year, and I had to pay for my own health insurance. There's so much you just said that I want to talk about. Let's first go back.

Well, let's start with something you just said. As a legal duty, a moral duty, a lawyer has to do what's in the best interest of the client. With a divorce lawyer, it's the incentive to do better for yourself than the client is bigger than any other part of the law, right? You could go to mediation and a mediator could cost $5,000, $20,000. I have one right now. And the goal of the mediator is to settle without going to court. Court's expensive. I'm a high net worth individual. Legal fees could be easily a half million dollars, half a million dollars. But a lot of lawyers' job are not doing

what's in the best interest of the client. They don't want to mediate. You know, lawyers play a role of psychologist, psychiatrist, right? You've got someone who goes, I can't believe what fucking happened today and my divorce, what my husband did, what my wife did. But there are a lot of lawyers out there. They have reputations. When I was looking for a lawyer, it was, okay, who actually is known to settle? Who's not self-interested in the money? How does one figure that out when they're hiring an attorney? Yeah. I mean, gosh, there's a lot there to unpack. So what I'll say to you is as a trial lawyer who has a reputation as being a very effective sort of weapon in a courtroom. What I will tell you is it makes a lot of sense when you're a client and a consumer who's in need of the work that divorce lawyers do

to think that the right way to approach it is to hire someone who has a reputation as being settlement-minded and more of a non-aggressive attorney. Unfortunately, in my experience, that often results in people ending up more in litigation than not. I think it's better to be a warrior in a garden than a gardener in a war. Like, it's better to have a gun and not need it than to need a gun and not have it. And a trial lawyer is a weapon. What you said is absolutely accurate, which is you should never do something with a chainsaw that you could do with a scalpel. Mediation as a technology is doing it with a scalpel. And I always tell my clients at the beginning, like, you don't want to use my trial skills. Like, don't.

like do everything. It's kind of what I told my sons when we were growing up, you know, when they were growing up, like, don't use violence. Like, don't use violence. Like, I'm good at violence. I've been training Brazilian jiu-jitsu, Muay, boxing for many, many years. I know how to use firearms really well. I'm really good at violence.

Don't use violence. Do everything you can to avoid violence. All of the, like, highest level jujitsu guys, tactical military guys I've represented. you know, FBI SWAT guys, they would all do almost anything to avoid using violence, even though they're graded it. Like Chris, you know, Petrus, you know, who's Navy SEAL, former Navy SEAL, amazing at violence. Jocko, amazing at violence, would do almost anything to avoid using it, you know,

apologize when somebody scuffs your shoe and it's their fault, you know, like they just don't feel the need to flex because they're good at violence. Hoylor Gracie, phenomenal at violence, you know, but one of my dear friends, one of my teachers, lives in La Jolla, would do almost anything to avoid the necessity of using violence, you know, but incredibly effective at violence. A good trial lawyer, it's the same thing. Sometimes the better you are at the art of tactical violence that is being a divorced trial lawyer, the less often you end up having to try cases very often. Like I said, I was talking, and last time we spoke about John Teitler, who's really, you know, one of my adversaries in court, but one of the people I

respect most as a tactician and strategist. He does almost anything he can to avoid his clients having to litigate their case. But my God, is he an effective litigator if litigation is what's necessary. And sometimes the fact that he and I are both very good at litigation is exactly why we don't end up litigating a case. We just had a case together where, you know, hundreds of millions of dollars potentially in play, millions in counsel fees easily could have been spent. I think we both probably settled it. We settled it in like two months and probably with 20,000

in legal fees on each side, which was a drop in the bucket for these people. I mean, the retainer they would have paid would have been $50,000 to $100,000. But John and I both as high-net-worth divorce lawyers, meaning divorce lawyers who work with high-net-worth clients, we just, you know, we both realized, look, this is the argument you'd make

is the argument I'd make, this is what the judge would probably do with it. Like, what are we doing? Here's the delta between what our respective position, would be, here's what the legal fees likely would be if we fought those positions and you got your blue sky scenario or I got my blue sky scenario. Here's the difference in our positions. So let's just get there. Let's just get there. And we got there very fast. And that's what a good lawyer does, what a good mediator does. Mediators do it until everybody's satisfied, you know. And so the goal should be to try to get there without the litigation. But sometimes the, you know, there's an old saying

that cops carry guns so they don't have to use them. You know, good people, people, going through divorce litigation. You see good people at their worst when you're going through divorce litigation, even the friendliest divorce. Mine was, you know, my divorce personally was one of the friendliest divorces you could ever ask for. We went through mediation. We're both compromised-minded people. We both cared about each other. We had children together. We didn't want to hurt each other. We were never good at hurting each other. Never wanted to hurt each other. She's still one of my favorite people in the world. I still, there's a lot of people I love. I wouldn't want to be married to. Actually, all of them. So, you know, I really never wanted to. I really never want to be married to. I'm

wanted to hurt her. And I said to her from the beginning, like, listen, you know, have you ever seen me, you've been married to me for 10 years, we have two children together, have you ever seen me screw anybody out of money? Ever, like a contractor, a waiter, anyone in our entire time together. We've known each other since we were 19 years old. Have you ever seen me screw anybody out of money? She said, not once ever. I said, have you ever seen me get screwed out of money? She's like a couple times a week. And I said, okay, do you think I'm going to start screwing people out of money? And the first person I'm going to do it with is a person I have two children with and I'm going to have grandchildren with. She was like, no, I don't have any reason to think that. So,

you know, that's why we went to mediation and we were successful in ending our marriage in a very amicable way. But it was still very painful. You know, you was still difficult. It's a transition. Change is good, but transitions are hard. I hope you're enjoying this video so far, but before we jump back in, I want to know if you've ever thought about what you need to do to reach a nice level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lift and Seagate. And I also co-founded a company that today is worth more than $15 billion. I've been incredibly blessed in my journey.

And at this stage in my life, I want to give back. I want to share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions.

And if you're a good fit, my team will reach out so we can build a game plan together. All right, now let's get back to the video. Chris Voss, who we both know about this amazing book, Never Split the Difference. and one of the great things about his book is never take advice from someone who hasn't been in the same situation themselves. So I got divorced a long time ago, just because the divorce lawyer I had then, who I didn't think was that great, by the way. This time around, I said, okay, who do we go to? Do we go to people we know him respect who have recently been through? In this case, I went to a friend Jeff Sclar.

Great lawyer, has his own law firm, Justice Stud. I'm familiar with Jeff's work, and I've worked with people who had Caltech. California issues and New York issues as many high net worth people have a place in California, a place in Florida, usually Miami, and then they have a place in New York City. And so there's a jurisdictional thing that happens. So I'm familiar with his firm and his work as an attorney. And, you know, he's got an impeccable reputation among the bar. And, you know, it's cool.

Like one of the things is when you know someone that long, I don't have to go through a receptionist and a conflict check. You know, it's like, hey, Jeff, text them, Randy, you know, what's going on? He gave me Gary Fishbine, who's been fantastic for me. So I had a great referral who I really didn't have to look that much. I interviewed Gary to other people. But I have the resources and the relationships to be able to do that and get to the best of the best quickly. What's your advice to people who are not in my position or your position who don't know anyone?

How do they pick a divorce lawyer who's in their best interest? It is not like better call Saul on TV and it's going to screw them over. I hope you're enjoying this video so far. But before we jump back in, I want to know if you've ever thought about what you need to do to reach a nice level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lift and Seagate. And I also co-founded a company that today is worth more than $15 billion.

I've been incredibly blessed in my journey. And at this stage in my life, I want to give back. I want to share the lessons I've learned so you can reach incredible. success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions, and if you're a good fit,

my team will reach out so we can build a game plan together. All right, now let's get back to the video. Yeah, great questions. The right question. ask, you know, you can't believe people's marketing. You can't believe any of those like super lawyers or top lawyers things because those are all really paid marketing behind the scenes. You can't really trust what a Google search will tell you or what Claude or chat GPT will tell you because they're really just taking aggregate information from a lot of marketing sources. I think you have to go to mental health professionals who work with high net worth individuals. You have to go to accountants and trust the estate's attorneys who work.

with high net worth individuals. You know, high net worth individuals are not, are not unfamiliar with working with lawyers. You know, they see lawyers as what they should see lawyers as, which is a service profession. There's an old joke that I hope won't offend you that, you know, you can't scare a prostitute with a dick. And I think that, you know, you can't scare a high net worth person with lawyers because they've, if you're nobody till someone sued you. And all of my high net worth clients, athletes, celebrities, CEOs, C-suite executives, um, you know, entrepreneurs. They've all worked with lawyers.

They've all been sued. They've all had to sue someone. So you go to the professionals who high net worth individuals trust and have earned their trust, the good accountants, good financial managers. You ask them, you know, who have you seen your high net worth clients work with? Right. I mean, the majority of people, though, watching this podcast are now, are not high net worth people.

So let's say you have $250,000 net worth. You're making $100,000 a year, $200 grand a year. You have a mortgage, no liquid assets. You know, a lot of people like that where the net worth is tied up in their house. What's your advice to people like that who don't have the relationships and are not high net worth and don't have the best service providers? Yeah, you know, even if you are that person, even if you're the cop or the teacher or the, you know, the non-high net worth person, a person makes, you know, a couple hundred thousand dollars you're still putting you by the way in a fairly small percentage of americans you know you you still have an accountant probably who you've dealt with you probably have a real

estate attorney you've worked with you probably have um someone who did a will for you um we've we've all bumped into lawyers whether we like it or not you know we have somebody who helped us get out of a speeding ticket you know you go to those professionals and you say to them who is trustworthy i will tell you without divulging any attorney client privilege i have the attorney general of a state, not New York, who hired me when I was a young lawyer, a younger lawyer, to represent their son in connection with a custody proceeding. And I remember I was quite a green young lawyer. You know, I still had the price tag on me. I was still wet behind the ears. But I was very dedicated, very passionate, young, smart, and hungry, which is what I was

when I was a young lawyer. And I'd like to think I still had the same level of talent, although I didn't have the same level of experience. I had the same level of skill, but I didn't have the level of experience I have now. And I remember getting the phone call from this person. He said, hi, I'm John Smith, a pseudonym. And I'm the attorney general of blah, blah, blah. And I went, okay? Like, what did I do? You know, I don't think I've even been to that state. Like, I can't have done much, you know? And he said, no, my son has an issue. It's in New York State. And I'd like you to, you know, to do a consultation and maybe work with him. And, and, and, and, and, and, and, and, and, and, and, and, at the end of the consultation, at the end of the conversation, I said to him, you know, I'm sorry.

I really just am dying to know, like, how the hell did you hear of me? Like, I'm nobody, you know. And, and he said, I'll tell you the truth. He said, I called, I called the clerk at the courthouse. I called the woman behind the glass who you see when you go into the information desk. And I said to her, who I said, could you tell me, I'm from out of state, who's a lawyer who behind the glass, the judges and the court staff speak favorably of. And they said, oh, Jim Sexton. He's like a young lawyer, but like everyone really likes him and respects him and finds him to be like prepared and thoughtful and organized. And he said, great, I'll find his number. And then he, you know, Googled me or whatever and found my number and reached out to me. And really what she was talking about, she's retired now,

that clerk named was Diane. She just had a unique perspective being behind the glass and like hearing, you know, what the judges and their staff, their park clerks, their court officers, like what they had to say about me. And she said, people say, yeah, Jim's a nice guy, but he's also good in the courtroom, and he's thoughtful and he's organized and he shows up prepared. And this guy as an experienced attorney as an AG, he knew that that was, you know, that was what the tool requires. That's the tool for the task, you know, is someone who's organized, thoughtful and

prepared. You're starting a company, you're planning a business, you look at the whole field, you survey, you do your research, and one of the things you think about is knocking out your competition. And it's great to knock them out before you even start. So one of the thing that goes on is, you know, it's sort of like forum shopping, where you make a list of the biggest asshole lawyers who are known, who you don't want on the other side of the table, you get on a phone call with them, you get a screening, they run a conflict check. And then your soon-to-beck spouse cannot call that person, then they cannot represent you. We talked about...

The Tony Sopranos strategy. It was an episode of The Sopranos. Yeah, well, so it's been going on forever. That's what someone told me to do in my first marriage. That's what people told me to do in our second marriage. How many people do that to you? And then what's your take on the whole thing? I mean, it's very easy for someone just to knock you out with a 10-minute phone call.

Yeah. I mean, I actually think it's an ill-advised strategy. I think that it's a good strategy if you applied it to getting, conflicting out the lawyers who are assholes, the lawyers who are ineffective and not good at family law. Some of my most tenacious, skilled adversaries are exactly who I would want on the other side of the case. Because like the story I said earlier with John Teitler, who again, I consider to be one of the most effective. weapons available in a courtroom. He's also just, he's effective, but he's not a jerk. He's not unnecessarily, like, you live and die by your reputation among your real peers and among, like, judges. Like not what court staff and judges and your adversaries, your skilled adversaries,

think of you as what matters. Like, I will tell you, as a long-time divorce lawyer now for almost three decades and also as someone has represented a lot of celebrities and has a small measure of celebrity myself now as a function of my media work and my profession. I will tell you that, you know, one of the things about being a celebrity or quasi-celebrity and what I'll tell you from representing celebrities and spending a lot of time with celebrities is a lot of celebrities are really, really interested in the praise of strangers. The praise of strangers never meant that much to me. It's one of the reasons why celebrity or the modicum of celebrity that I, that I enjoy, and certainly representing celebrities, it's never really been that important to me.

Like, because praise of strangers is lovely, don't get me wrong. Like any person who comes up to me on the street, like when I walk to my office, the three blocks I walk from my apartment to my office, I get stopped four or five times. Usually my people say, you're the divorce lawyer. I know you from TikTok, or I've seen your videos or I read your book. I really liked it. Thankfully, very few people ever say mean things to me. They usually say nice things to me. It's actually why I understand how some of my celebrity clients can be assholes

because you're just getting constant affirmation thrown at you all day long. Imagine you walk down the street and people are like, I love you, man, you're awesome. What a weird thing, you know? But they're strangers. They don't know you. And it's not a drug you should get, like a need, develop a need for.

Like, because it's a, you know, fame is the mask that eats into the wearer. So for me, being respected by the people I respect. is important, you know, people that I hold in high regard, holding me in high regard is important. People who I hold in high regard thinking poorly of me, that's something I'll feel. But what strangers think of me, what people in the comments section think of me is not, it's lovely. Like, but, you know, if I believe the good reviews, I have to believe the bad ones too. So I really don't, I just keep moving and try to do the job as best I can. What I will say is bumping out lawyers on the other side of your case or ineffective and known to churn cases might be a fine idea. You do not want your spouse to hire

Bob the real estate lawyer who has no idea how to do divorces because that's the only lawyer you haven't conflicted out. You want your spouse to hire an experienced, thoughtful, well, well respected matrimonial attorney who knows what they're doing because we're going to save everybody a lot of time by not arguing over dumb things. And we're going to understand like, what's worth fighting about, what's not worth fighting about. I just literally, right before we started this conversation, just finished the court appearance. And it's with an adversary who I've had many cases with Larry Greenberg,

very talented lawyer in New York City, high net worth divorce lawyer. We had a brutal case against each other with 13 days at trial, you know, $800 million marital estate. It concluded about a year ago. And now we have another case with each other. It was a court appearance, but it was a very friendly court appearance because we both understand the assignment,

which is to get these people through this thing, and to accomplish our client's goals, our respective client's goals, identify what are the issues that aren't in dispute, identify what are the issues that are in dispute, and then figure out a way to efficiently resolve those disputes, whether that's by negotiation or litigation. And if we're going to litigate it, litigate it efficiently.

And that's what the assignment is, and that's exactly what we just showed up in court to do. It's not time to start fighting yet. Like when it starts to, it's time to start throwing hands, we will throw hands. But it's not time to start throwing hands. throwing hands yet. So there's no reason to be discourteous. There's no reason to protract things. Like there's no reason. People, part of this job, a big part of this job, is getting your client

to start to view their divorce as a business transaction, not as a breakup and an emotional situation. I'm not suggesting it's not okay to be emotional. We're going through divorce. Everyone is emotional. We're going through divorce. But the sooner that you realize that the outlet for your anger, your hurt, your frustration. The courtroom and the litigation process is not the best place to do that. In fact, it's one of the worst places you could try to do that. I want to back up for a second and talk about relationships in general. We'll go back to the beginning and you mentioned business transactions. Sir Blakely, the founder of Span, is one of the greatest entrepreneurs of our day. Married to Jesse Isler, great entrepreneur as well,

was on my show. If you haven't listened to that, I hope you guys do listen to it. he's a stud as well. You've described relationships and you know you talk about first dates and you know first dates are everything I've ever done their best behavior and you're polite and you've described them as spanks for your personality. Talk about what you mean by that and then also go through the first date progression that you've talked about. I'm so great I'm on my best behavior and then what happens after that? Well I think you know I think on the first day you're interested and you're trying to be interesting. And you're super mindful of the assignment, which is, you know, I want this person to like me and I want to be someone this person likes and I want to like them. I wouldn't

be on a date with them if I didn't want to like them. So we're both here with a genuinely shared purpose. Now, again, we might have a different end game in mind. I might be looking to get laid. She might be looking to get married or vice versa. But we're both trying to, you know, connect to the other person in some fashion and for some end. What I say, Spanx, your personality, what I mean is that Spanx isn't lying. Makeup isn't lying. It's accentuating the positive and dissentuating the negative, you know? And really, that's what sales is, right? I mean, sales is not the worst salespeople lie. You know, the worst salespeople go in and, and represent that this product doesn't do something that it does or does something that it doesn't do. Like,

that's ineffective sales. Or you go in and pretend in a very, you know, pass it or real way that you're not looking to sell this person something. Of course you are. Let's be mixed with each other. Again, it's the difference between going in and saying, hey, I would like to have sex with you, so I want to take you out to dinner. That's a little too honest to some degree, right? So you wouldn't go in and say, listen, I want to separate you from your money in this sales call. That's not what you do. You're going to say, look, I want to understand what you need for me. I want to meet your needs. And you know what? I'd like you to meet my needs as well. I'd like to see if there's some accommodation that we can do something for each other that's mutually

beneficial. And that is what a date is. It's a sales call to some degree. And I think, you know, when I say you have spanks on your personality on a first date, what you're trying to do is you're trying to present the best version of yourself possible. And I don't think there's anything wrong with that. I think it's part of the dance of dating and romantic love. And it's one of the most enjoyable parts. But of course, the goal is not to go on an endless succession of first dates. the goal is to find depth with another person. And depth and novelty are kind of at odds with each other. And I think that you have to, early on in a process,

I think start giving this person a sense of where you are wearing spanks, where you have on makeup. Like, I would like to see a woman who I might be serious with. I'd like to see her without makeup or with less makeup fairly early in the relationship. Do I want her to show up on the first date without makeup on? Probably not. I think it's lovely that a person would

try to present the best version of themselves. I know if I'm going on a date, I'm going to wear something nice. I'm going to wear a little cologne. I'm going to shave, you know, unless I want to do the oops that didn't know it was sexy stubble thing. Like, I'm going to give some thought to it. You know, ideally, by the way, even at our 50th date, I'm going to give some thought to it.

But I'm not going to be afraid at that point to let this person see me in a very natural state or vulnerable state, because there's a lot of good reasons to do that, too. You mentioned questions to ask someone to go on a first date, and I just have to comment as a newly single guy, going up to a woman and saying, hey, nice to meet you, do you want to go have sex?

It's not an effective strategy. Probably not effective. Yeah, it's probably not effective. Yeah, it's probably not the kind of person that you want to be with on a long-term basis and establish long-term intimacy with. I mean, obviously, hookups, having sex on first days do happen, but I just don't think that's a good opening line.

I don't think you're going to win a lot of sales calls on that one. And I don't think it's one that's going to accomplish the goal. But I do think, by the way, there is value in having a conversation about the conversation. Like, I think there is something charming on a date about acknowledging that you're on a date and you're on a first date. And, you know, like, hey, how do you think it's going? You know, like, ooh, like I'm a little nervous. Are you nervous?

Like it's kind of fun. Like so far this is going well, don't you think? Like, or if you've loved something saying like, I feel like I flubbed that. I just want to say, like, I feel like if you're going to grade me later on this, I really hope that is not going to make it to the phone call that you make to your best friend later. You know, like there's something charming about acknowledging that this is a little weird. Like, this is a little surreal. Like we're, but it's also so beautiful to say like, you know, oh, aren't we both, aren't we both a mystery a little bit right now?

Like, is this an interesting moment in the connection of the two of us? Like, I wonder if we'll look back on this someday and be like, remember that first date. Or if it won't be anything that needs to be remembered. Like, if it will just have been a moment that we shared. Like, I think there's something really cool about acknowledging when you're in a story that you're in a story. Some people say dating is like a job interview. There's a sign on, there's a clock on my desk. It has four words on it.

Now, now, now, now. And do it now is part of how I do things. Mel Robbins talks about it all the time. It's been a hallmark of my success in my career. And I always coach people in my coaching business to shorten the time between ask and result to maximize your probability of success. And that's true in relationships as well. I know you've talked about that as well. So what are you talking about that T minus 1 to 0 should be a shortest point?

possible to maximize the probability of going out on a date. And then the corollary is, how has do it now been part of your success as a great attorney? Yeah, I mean, I think fear holds us back a lot. I mean, that's no great wisdom to share. I mean, that's something everybody, I think, understands. And I think we lack sometimes as a species, the self-confidence and also the humor. I mean, I think I try to find humor in a lot of things. Like, I think we're quite thoughtful. all of us. I mean, I think our insecurities are funny. Our fears are funny. Like in a long enough timeline, and one of the things I'm very much enjoying about late middle age, you know, being in my 50s, is just how much of a timeline I've now seen, experienced, you know. I saw one therapist for about

20 years and then he retired and I had to get a new therapist. And I remember when I got my new therapist, you know, it felt very frightening because it felt a little like a date, like a date, like a first date? Like it felt like, where do I start? Like there's a whole, I'm not 19 anymore. There's like a whole life of stuff like that this other person, by the way, knew I seen me every week for 20 years. Like, they know I got divorced because I was sobbing on their couch going through it. They know my mom died from cancer because I was sobbing on their couch going through it. Like they know all of this little nuance stuff. How would I ever start over with someone? Okay, well, I'm either not going to be in therapy.

or I have to try again. I have to go in and start this new relationship. And one of the things that was so fascinating to me about starting with the new therapist about two, three years ago was how in the Wikipedia page of my life that I was describing to this therapist, there were things that were four sentences

that felt like they were the entire world when they were happening. I remember saying to her like, yeah, I was married to my college sweetheart, and, you know, kind of grew apart and we divorced when the kids were five and seven and we've stayed very friendly since. Are you serious? Like that was like six sentences. But it was when I was going through it, it was five or six years of like, oh my God, are they going to be okay? Is she going to be okay?

I don't hate her. I love her. I don't want her to not be okay. And will I be okay without her? I think I will. I think I need to be and I think she needs to be too. But my God, like I don't know. and just sort of realizing that, gosh, you know, like it's not even this giant thing. Like, I'm sure there's chapters of your life that you look at now and you're like, it's literally this. I mean, I literally have a Wikipedia page now. And when I read it, I laugh because it's like there's three sentences. And then I go, yeah, that was the whole thing.

And it's very fascinating that it was whole chapters of my life that are now, you know, condensed to this thing. And I think when I now as an adult man, when I enter into an interaction with someone, whether it was in the dating context or it's a relationship business context or anything, you can't take from me that knowledge that like, hey, this is a thing and it could be a really big thing that changes the trajectory of my Wikipedia page or it might not be. It might be nothing, you know. But whatever it is, like I feel like I've been through so many things. I tell people all the time, friends, that like once you've been divorced, with children, you feel kind of bulletproof in some ways, because you realize, like, it's just like when you've had, like, a business and you've seen it fail, and you've survived that. You sort of go, oh, okay, like, so I could try really hard and still fail and I'll still survive. Like, okay, like, I feel a lot more open and brave and a lot more willing to just, you know, like, yeah, let's just see what happens here. Let's try. Let's try some things and see what happens. And so I think

That's, you know, a lot of what I try to say to people is in that interaction of like going from the starting place to the place that's closer to where it is you ultimately want to be. Like, just get there more open, more, more be bold, you know, just be very open about, where is this? What's going on? How is this? Is it working? Is it not working?

What are we doing? So you date, date leads to progression. Progression leads to supposedly love. and then you get married. And we'll talk about supposedly a little later in the show, but what are the three main reasons why people get married? I think the main reasons people get married are, one would be societal pressure,

that there's a external pressure exerted by society that you're supposed to get married. The simplest expression of that is to say, if I said to you, you know, Randall, I'm in a really great relationship for the last few years, and we've decided we're going to get married. Your response is, oh, congratulations, that's wonderful.

Not really, why? Like, why? Like, you're talking about a technology fails more than 50% of the time. Why, in God's name, but you said you're happy? Why, it's not broke? Why you need to fix it? Whereas if I said to you, maybe not to you, but to most people, yeah, I've been in a relationship for a number of years and we were talking last weekend, we decided we're not

going to get married. You would go, I'm okay, I guess some intimacy issues there. He got an avoidant detachment style, what's happening, you know? You wouldn't look at it and go, yeah, that makes sense. Why would you get married? It's a terrible preposition. I mean, statistically, it's a bad idea, you know? So there's an assumption you should get married

and that if you choose not to marry, that you must not have sufficient faith in the relationship, which, again, runs contrary completely to statistics. So that's the societal pressure piece. Two, I think there's still a tremendous, you know, religious and familial. I'll lump those into the same category, a familial pressure or a religious pressure to marry. to legitimize a relationship,

the old saying about, are you to make an honest woman of her? You know, again, I'm not sure where that comes from. I, you know, I think tradition is in some ways the wisdom of the people who came before us and what we can learn for them. And tradition is also peer pressure exerted by dead people.

So it's really a question of, are you going to make your life, you know, on the trajectory of it, impacted by pure pressure exerted by dead people. I personally don't think that's a very good motivation. But do we have things to learn from the people who came before us? I do. I think that, you know, there's, grandmas have a bunch of remedies for different ailments,

not just because they're grandmas. Like, they do something, you know. So I think, but you have to separate the wheat from the shaft, you know. So that's number two. And number three, getting married's fun. Like, it's fun. Like, getting married is the most, one of most enjoyable experiences a person can have.

Being married is one of the most challenging experiences a person can have. But getting married is a blast. It's a party. It's food. It's the booze is flowing. My son, my oldest son got married a few months ago. It's the most enjoyable experiences of my life being at that wedding and watching it and being around him and all of his friends and this lovely young woman who's so enamored with this lovely young man.

who I helped teach that the cow says moo, you know, and she's sitting there saying, you know, you're the best man I know. You make me feel so safe. Like, I don't think I've ever felt such pride as I did in that moment. You know, every home run he ever hit, every A he brought home from school was nothing compared to this young, beautiful, lovely, self-assured, accomplished woman looking at my little boy and saying,

you're the best man I know. You make me feel safe. Like it was a finished line of sorts. It was the most beautiful thing. And yet it was a starting line of sorts and such a beautiful thing to be part of and to bear witness to and to feel like I got to see the beginning of a chapter that would be so lovely. So again, you know, I think there's lots of emotional reasons that we want this thing. It's the triumph of faith over reason to some degree. Let's talk about the statistics. I mean, we have a lot more staff to talk about. but you mentioned 50% and in divorce, that's not a very good number. I do like playing the lottery when it's $300 million,

although my odds, I think, of one or $200 million. This is kind of like one or two, and there's a, there's a 1989 movie called Drugs, a Cowboy director, about some of the Monsana, a great movie. Matt Damon has a famous line. Tell us about that line, and then tell us about your great, famous toast that you make at weddings when you're asked to give a toast. There's a line in Drugs for a Cowboy great film

where Matt Dillon's character says, we played a game you couldn't win to the utmost. And I find that line just gives me chills. It's so beautiful. I think the idea that you would play a game you can't win to the utmost. Because I think that's what we're doing in life. I mean, you're going to die.

I'm going to die. And everything we own, everything we accomplished will add up to a great big pile of nothing to some degree. You know, I look at, I look at Madonna as a great example. You know, Madonna, when I was growing up, was possibly the most famous person in the world. And now if I say to my 26-year-old son, Madonna, he's like, oh, that kind of weird-looking lady who had all that cosmetic surgery? Like, he doesn't even know really who she is. I understand that that's the nature of fame and celebrity.

It's the nature of the passage of time. You know, 100 years from now, no one you love will be alive. and 100 years from now, no one who loves you will be alive. And so when you think about that, and you think about the fact you've already lived half of that time period or more, you realize that, you know, all of this stuff is not, you're playing a game you can't win to the utmost. Ideally, you play it and you play it hard

because it's the experience of playing it. Like the purpose of dancing is not to move from one side of the dance floor to the other. The purpose of dancing is to dance. You know, the purpose of dancing is to experience the sensation of that movement and that moment and to feel it. This is what this is about. Like marriage, you're going to die. Like your marriage will end. Every marriage ends.

It ends in death or divorce. You're playing a game you can't win. But the point is to play the game to the utmost. The way to win is by playing. And by playing with everything you have. It's why I refuse to say that my first marriage, failed. I don't feel that it failed. I think that it accomplished what it was supposed to accomplish. It produced two amazing children. It made me a better man. I hope she would say it made her life

better too, that the connection we had together, you know, was a productive one. And then it ended. You know, the marriage ended. She went on to marry another man who's a great guy and she's been married to him almost double the amount of time she was married to me. So obviously it was a good choice. She chose well. So I think that it is a game you can't win. But it's a game that that in some ways you can't lose either if you approach it the right way. You see so many people fighting and you see different personalities and you get reasons for conflict and a divorce. We're going to talk about all of them cheating,

which everyone wants to talk about. It's a huge topic based on the hundreds of people you represent over the years. Are there groups of people or personalities who should not get married? Yeah. I don't think marriage is for everyone. I think we've created a one-size that's all approached to it and told everybody that it's something they should all do. And I just don't think that's true. And, you know, I hate to use the same metaphor, you know, because it feels a little profane for something as important as marriage as such a lifetime loving commitment.

But like, not everyone should own their own business. They just don't have the Constitution for it. Like, some people should work for people. You can be perfectly happy working for someone. If you find the right boss or the right company, you can have a very satisfying. My partner, Colin, my law partner, Colin's been with me 15 years. He's very happy not running a law firm. He's very happy working for me.

And I'm very happy with him working for me because I'm very much control-oriented and I like to make all the decisions and I like to do things by committee. And he trusts me and I've earned that trust. And, you know, we work wonderfully together. I think he's smart. He knows, I said to him many years ago, like, hey, do you want to be like an equity partner and we'll do it a different? He said, no, this is great, man.

I'm having a great time. I make a lot of money. I enjoy my work. I have time with my family. Why would I ever want to do that? And so I think knowing, there are some people that I think are not wired for marriage, but I think the metric is very,

I mean, obviously I could explain, I think it's very easy to say that there are certain types of habits and personality traits that are antagonistic to marriage, people with serious substance use issues, you know, getting married's a bad idea. People who are incredibly uncomfortable being alone to the point where being alone causes them to sort of spiral into a sense of not having any identity,

I actually think you shouldn't get married if you're that way, even though marriage will probably be one of the most appealing things to you because it's, oh my God, I'm going to have a person and I won't ever be alone. I think that's actually a terrible reason to marry because I actually think that to have really effective romantic relationships, you almost have to resent me. this person for taking you away from your solitude. You know, I've always said in my post-divorce dating life to any woman who would date me, like, if you're going to rob me of my solitude, you owe me companionship. Like, you owe me quality companionship because I love being alone. Like, I have a very

social job. I have a wonderful media presence where I get to have lovely conversations like this one. I am never lonely, you know? And if I'm sleeping alone, it's because I'm I'd like to be. You know, so I'd like to starfish out in the bed. I enjoy sleeping alone. So, but do I enjoy companionship? Quality companionship, of course. Who wouldn't?

Who doesn't? So I think it's okay in the economy of a relationship, you know, and I'm sure we'll get into that. I get criticized sometimes for referring to relationships as an economy, but I think every relationship is an economy. You know, an economy is an exchange of value between two people. And it's an ecosystem of sorts. So I think a romantic relationship, including a marriage, is an economy.

It's an exchange of value. And an exchange of value is not how many pineapples is worth how many pineapples. One, that's really easy. It's how many apples is worth how many pineapples. Now we're having the conversation because apples and pineapples are different things. And so how much is an apple worth to you? How much is a pineapple worth to me? That's a conversation worth having.

But in marriage, we've created this approach. culturally, where it's just supposed to be, do you love the person? Well, then you should marry them. Okay, that's insane. You're not giving any honest thought to the economy that is this relationship. I think at my age, I'm 57, you're 52. We've both been on the single scene for a little while. I've been single now for eight months-ish right now. We're going to talk about what the dating world is like in a little bit. But as I've been older, I have a lot of female friends. Obviously, there's a certain age at which a woman should have a baby from a health perspective and how every year they're after, especially in your mid to late 30s,

the chance of going something wrong with your baby increases by a material percentage. I know a lot of women. I'm not talking about men right now because there's a lot of reasons why men get married and we'll talk about that in the show also. But I have so many women friends throughout the years who are telling themselves, I'm going to settle, I'm not going to love this person, I'm not in love of this person because I want to have a baby. What are the top three reasons while people should get married?

I mean, my answers are going to be wildly unromantic. I think the three best reasons to get married with a pre-up. I don't think anyone should get married without a pre-up. We can talk about that later. By the way, I think everyone has a pre-up. It's either one written by the government. It's one written by the two people that like each other more than the 8 billion other options. So every relationship has a pre-nup.

It's just, do you trust the government, write it for you. I generally don't. Because it's not even the present government. It's the government of future that you're imagining and hasn't happened yet. So that's crazy. If you're saying, do you trust the government, I don't even trust the current government, much less the imagined future government. That's a lot to ride on. So what are the reasons to get married? I think the best reasons to get married are, A, it's super fun to have a wedding. And it can be a way to solidify your intention together and to express it publicly in a way that's meaningful for both of you. And also, I'm a fan of ceremony, and I think it captures some ceremony.

I think that the older I get, the more I've come to value symbolism. I think we live in a world of symbols, and I think that there's something beautiful about the symbolism of marriage if you both share that symbol. So, you know, the idea of wearing a ring because you want to be reminded physically of each other at all times and you want other people to see a symbol of your commitment and to each other. I think that's very beautiful. And I think there's something beautiful about a wedding itself. I think if the first time everyone you love is in the same room celebrating you

as your funeral, you're an idiot. I think you really should have moments where you celebrate, whether it's birthday parties or whether it's whatever. You should have moments, celebration. Some of my greatest memories of life are from symbolic moments like that, weddings, you know, funerals, birthday parties, things like that. I think there's certainly still tax benefit to getting married and financial benefit in terms of being able to be on each other's health insurance, things like that. I know that's unromantic to say, but there is a certain pragmatism to it. I also think many hands like work.

I think that life is challenging. But that's not marriage necessarily. That's pair bonds. Like I'm a big fan of pair bonds. Marriage is just something we've put on that to say, okay, this will shore it up, you know. But I was like putting a fence around your house and saying, okay, now I'm totally safe and no one could ever rob me. Like, no, people can scale fences, people can cut through fences, people can open the gate to fences. Like, don't kid yourself by thinking that because you put up a fence,

now you're safe. That's just dumb, you know, just like saying, oh, I love this person and they love me and it's really, really good. So now we'll get married and it'll stay that way. That's insane to think that. But I do think there is some value in the symbolism of it. And I do think that there's some enjoyment in celebrating the symbolism of it. And I do think it does create opportunities to to shore up certain things. Proximity to another person and having someone, like if I could see my own blind spots, it wouldn't be blind spots.

Like, they're blind spots because I can't see them. And I can't learn everything I need to know about myself from myself. I need people to help me see those things. And people who are coming at it with a real commitment to my best interests. You know, people who are coming at it and saying, no, no, I love you. And I'm going to tell you things you might not want to hear

because I love you. And I'm going to tell you things you need to hear because I love you. And I'm also going to cheer for you because the world is awful sometimes and hard. And to have someone who at the end of the day gives you that little bit of sweetness, that's one of the best things, in my experience, one of the best things about having a relationship with a woman, you know, for me is that little bit of sweetness at the end of the day. That's worth all the money in the world. Like, that's worth whatever the price tag looks like. To have someone who at the end of the day when the world has weighed me down and I've been out trying to slay dragons all day and I'm exhausted to have someone say to me like come sit

come rest come be with me just sit with me you know just spend time together smells nice and who you know has a soft touch like oh it's one of the greatest things of the world i mean i'll i'll slay dragons all day long if i can have that at the end of the day and we're even i don't count the cost i don't look at it and go you know my parents they didn't do everything perfectly but one of the things they did really well is my mom was a stay-at-home mom my dad went out and worked really hard, but my dad never ever talked about my mom like she didn't work. He made a point of like, hey, did you thank your mom for making this lovely dinner for us tonight? Like, he acknowledged that, no, she works in this home and I worked out of this home, but we're both really important to this

family. We both have a job, and that job's really important. And he was constantly thanking her for it. She was constantly thanking him for what he did. And I think there's something really beautiful about that. We're going to talk about factors that lead to positive relationships and negative relationships in terms of marriage. And we'll talk about stats throughout the show as well. One of the factors is length of relationship. There was a university study a few years back, 3,000 individuals about couples who dated for three years or more before marriage were about 50% less likely to divorce compared to those who dated for less than a year. And that dating for one to two years lower the divorce risk by about 20%. In your own practice, have you seen a material

difference between those who got married within a year as I did in my second marriage, we got engaged after three months, as opposed to those who've been married 10 years. You know, some people said I've got the 10-year itch right now. What do you see in your own marriage? And what do you see in your own practice? Yeah, what I will tell you, I'm constantly trying in my own practice to see if I see any correlations so that I can determine if there is any aspect of causation from my own sort of, you know, just where I'm sitting. Again, it's not the same as double-blind research. You know, there's, there is a good amount of research out there about marriage, about marriage satisfaction rates, which I think is actually more interesting than

divorce rates. Like, divorce rates is how many of this catastrophically failed. I don't know that that's all that people are interested in. I think people are actually interested in how many people would do this again and say, oh yeah, this was a good decision I made, not a bad one. You know, how many people 10 years in, 20 years in still really like their spouse? And by the way, how many of those people, if they hadn't married, would still have liked each other just as much 10 years later, 20 years later? Like, how much did marriage contribute to that? Or was it just that this person met the right person

and then knew the habits of how to stay connected to that person? I don't know that marriage was the thing. You know, it's kind of like we're mixing up the causality aspect of it, you know, that are they happily married because they were right for each other or are they right for each other because they got married? Like, you know, I think it's much more that the marriage is like the frosting on the thing as opposed to being the thing itself. So I genuinely believe that I don't see those statistical correlations. I've seen people that got married very quickly and hardly knew each other. And I've seen people that waited a really long time. In my observation, I think

a sweet spot is like a couple of years, because I think a couple of years into a relationship. I think it's more about experience. Let me put it that way, because the reason I think a couple of years before you marry is a good metric, much to the chagrin of people who, again, are concerned about a biological clock or about, you know, all legitimate things to be concerned about, is that I just think you should experience some things. You should see the organism under stress. You know, I think Schopenhauer said, like to know a thing, know its limits. When it's pushed past its tolerances, its nature emerges. I always watch these shows like The Bachelor and stuff like that.

And they're like, oh, he was so romantic. And I'm like, yeah, you're on an island. Like, it's not hard to be romantic on vacation. Like, when you're on, everyone's having fun on vacation. It's like saying, oh, this is so good. It's ice cream. Ice cream's good. What are you talking about?

Of course it's good. Like, I want to see, you know, everyone at the job interview is somewhat impressive. Everyone drives slow when the cops are behind them. Like, I want to see what you're like when you're under stress. I want to see what you're like when you're sick. I want to see what you're like when you are upset at me. I want to see what it's like when I disappoint you. Or when you disappoint me, how do you handle it?

Or when I give you feedback on something, how do you handle that? How do you handle criticism? How do you criticize? And I'd like to understand that. And I think you could condense that if you were thoughtful about it. That leads to this question, which is in a lot of cultures, don't live together before you get married. Should couples do a mini-test and live together before they get married?

See, I don't know that the living together is the thing. I had a buddy who I've talked about before that moved in with a girl. He'd been dating for a while. And I got together with him for coffee. And I said, oh, how's it going? And he said, well, you know, it's hard when you first move in together. And I thought, no, it's not. Like, I remember mostly being having sex a lot and putting together IKEA furniture.

Like, it was great. Like, what are you talking about? Like, you first lived together? It's like, oh, my God, this is so fun. And oh, look at your little toothbrush you put there. And like, oh, like, having sex in different rooms of the house. Like, what are you talking about? That's crazy.

Like, it's early days. It's fun, you know? So, I don't know that there's so much to learn from that. I think that it's worthwhile to see this other person's environment in its raw state. I think that's really important. Like, I think when you're having company over, you clean the house up and you take out the nice tea set, maybe. So that's not a reliable indicator. But I think if you're dating someone and you spend time with them in their space, not when it's curated for your visit, but what's it really like? Are they neat? Are they messy? Are they someone who needs space of their own when they're working? Or are they someone who can work while engaging with you? These are all useful things to know if you're considering a long-term relationship with somebody. But again, I don't think the only way to learn that is by being in that person's actual proximity and living with them. I think you can figure out

what it might be like to live with a person by observing them. I think most of the things people need to see are there to be seen. But when you go through a relationship with rose-colored glasses, all the red flags look like flags. And that's the problem. I think that we love is a reflex in some ways. Like it's really easy to feel love. And love is a verb.

like love is a way of relating to another person. I'm going to treat you with love. I'm going to love you. I'm going to accept you. I'm going to be kind to you. It's a verb. So the emotion of love is really easy to feel. But the analytical aspect of it of saying,

okay, yeah, of course, I feel deep connection to you. I feel passion for you. I feel affection for you. I feel that about a lot of people that I wouldn't marry. Like marriage is about a very specific kind of connection. with another person. And what are the characteristics? If you can take off the rose-colored glasses,

because, again, I love love. I'm a big believer in love, but I don't believe in fairy tales. Like, I think fairy tales are really useful. Like, I grew up very Catholic. I don't believe that a person actually lived in the belly of a whale. You're crazy if you think that's a real thing. It's not.

You know, like, I've watched the Star Wars. movies, and I think they can be a beautiful metaphor. Obi-Wan Kenobi saying to Darth Vader, if you strike me down, you'll make me even more powerful. Is the same story as Jesus? The idea that you can kill me, but you'll never kill the idea that I've released into the world. You'll make me eternal by killing me. It's a beautiful story, but if you tell me wookies are real, you're crazy.

There's something to look with you. That's not a true thing. Wookies aren't real. There's no such thing as Chubaka. So it's the same thing. If you tell me, I want to feel with someone the feeling of like, you're the most beautiful woman in the world to me. And I want to love you forever. And I want this feeling between us to last forever. What a beautiful statement of intention. If you think 10 years into a relationship, you are still going

to feel that insane rush that you felt the first time you kiss someone, you're delusional. But you're going to trade it for something that's equally, if not more valuable than that thing. And I don't think that's unromantic. I don't think, you know, there's a quote from a Joseph Brodsky poem that I frequently say, I open my book with it, which is I wish I knew no astronomy when stars appear. Because there's something really romantic about not knowing what stars are, just seeing them as beautiful little lights in the sky. But I actually think that you can know what they are and they can still. be really beautiful and romantic. I don't think that conscious knowledge of a thing and the beauty of it are antagonistic to each other. We're going to get into cheating in a minute, but I want to follow up

on something you said about being Catholic. The Catholic religion, you're not supposed to have sex until you get married. And everyone today will look at, oh, I married my high school sweetheart. I haven't had sex with anybody else. Do, have you seen couples who have been through only one sexual partner in their whole life. Do they have a greater propensity to cheat? And is it your advice that people should have multiple sexual partners before they get married? Wow, those are some really big questions. So I've certainly seen people in fewer numbers, but I've seen people who were virgins when they married and they were each other's first sexual experience. Usually they come from a religious community, whether it's the Hasidic Jewish community or an extremely Christian community. I've had a

you Muslim clients that, but it's usually from a religious narrative. It's very rarely just because somebody just didn't get around to having sex. Like it's a primary biological drive. It's not the sort of thing people don't notice. It's usually a conscious decision to not marry. If you tell people you're not allowed to have sex until you get married, people are going to get married very young, period. I don't believe it's a coincidence that the average age of marriage and the acceptability of sex outside of the bond of matrimony, I don't think it's a coincidence that those two things have moved in the same trajectory. Like, I think that once we said, you're not going to be shunned if you have sex before you're married, then I think people said, okay, well, then I'll wait to get

married because it's not such an urgency. I mean, the desire to have sex is a gigantic drive. It's a huge motivator for almost everyone. So I think that has tremendous value. If you want to encourage people to marry, you would encourage them to not have sex until they're married. Now, is that a good idea? I don't know that it's a good idea. I think that we as a species, men particularly as a subsect of that species, crave novelty. I think that sexual novelty is more important, and this is not my studies, this is the massive data that's out there, it all overwhelmingly says that men enjoy hookup culture more than women do. And that's one of the reasons why the sort of sex and the cityification of Western culture

has been so abysmally bad for women. Because it essentially said to women, like, just have sex like a man. Like go out and have fun, like have novelty. And most women, when they are interviewed in a real clinical setting, and there's real long-term studies of this, A, they enjoy sex less and have fewer orgasms when they are having sex with someone with whom they do not have an emotional connection. And they don't enjoy hookup culture the way that men do. And if you want to see further proof of that, look at gay male culture versus lesbian female culture.

Gay men culture is a culture of hookup. Female lesbian culture is a culture of relationships. Hookups are not as important. Whereas gay men, they're having a great time out there, having lots of sex with lots of partners and enjoying them. as Grindr does not exist really in the lesbian community hookup app. I mean, there's approximations out, but they're nowhere near as popular as Grindr. Why? Because it's too men.

They crave novelty. They don't really necessarily see sex as something that's tied to emotion or relationship. It can just be something that's fun. And they find that as satisfying without the emotional connection. So I think if you look at like Sigmund Freud civilization and it's discontents, the idea that like marriage is a like a price you have to pay in order to have sex with, someone, I think that's going to be an effective way of getting people to marry. Because you can say you got to finish an obstacle course and develop an eight pack to get married and guys would be

much more prone to doing those things. Like if you said, you're not allowed to marry until you have X number of dollars, you would see a lot of very hardworking men all of a sudden. They'd be out there going, you got it, whatever I got to do to break through the barrier to have sex. I'm going to do it. So I think that it's a tremendous motivator for people. Do I think that the second question you asked, which is, do I think people should go out and have a number of of sexual partners before they marry. Statistically, the science on that is that it's generally not a good idea for women, meaning that women who have a high number of sexual partners often find,

they have a higher correlation to divorce. Men, it's not as high. Men seem to have the ability to have a lot of premarital sexual partners and not have it affect the likelihood of divorce. I'm not sure why there are a lot of people, Mike Sartain, a number of evolutionary biologists who've talked and written about this. I wouldn't claim that that's my area of expertise. What I would say is I have definitely seen a lot of men who had a high number of sexual partners and then successfully marry and stay married. I have not seen as many women

who had a very high, what they now call body count, and then had a successful monogamous marriage later, although the idea that a woman has to have limited or no sexual partners before marriage in order to have a successful marriage, I think is a fallacy. I have not found that to be true that women who have had a lower number of sexual partners don't end up in my office. I've seen a lot of women who had a variety of sexual partners before their marriage and their marriage ends. I've seen a lot of women who had limited sexual partners. That's a very human thing that the grass is greener on the other side of the fence. If you find your sexual relationship unsatisfying,

whether you've had a lot of sex prior to it or whether it was your first sexual relationship, I think people generally like having a satisfying sexual relationship. That shouldn't be breaking news. That's from the center for pointing out obvious shit. So I think people like having a satisfying sexual relationship. So if you consciously focus on keeping, keeping that metric of your relationship in a healthy place,

whether you've had lots of partners or limited number of partners. The worst pain you've ever felt is the worst pain you've ever felt. If the worst pain I've ever felt is a bee sting and the worst pain you've ever felt is having your leg lobbed off, the worst pain you've felt is the best sex you've ever felt. The best sex you've ever had is the best sex you've ever had. So if you had a bunch of sexual partners that now you're comparing your current sexual partner to in a negative way, that's bad. theoretically you should marry someone who you have a satisfying sexual relationship with listen

I've had the best meal of my whole life at a little cafe in Paris many years ago I can tell you it's not like when I eat a lovely meal in the United States they go well this is good but it's not as good as that meal in Paris like how do you think about that meal? It's a while I go oh that was really good it's a good enough reason to go back to Paris. But do I now find every other meal unsatisfying? No, I think that I have lots of me. I love Chipotle. I could eat there three days a week.

I really enjoy it. And do I enjoy it as much as that meal? No, but is it very satisfying? To me, it's lovely. So I think you want to find someone who have a satisfying sexual relationship with. That's what's important. I'm just going to make a statement about my own view,

and then we can just move on, which is, my own view on this is, sex is very important to every relationship. and my rabbi said to me, Steve Leader, who is a genius, he said, if you're not having sex with your wife, you're having sex with somebody else. And we're going to get into cheating in a minute from now. For me and a lot of my guy friends,

and I'm not generalized, I'm just speaking from my own view, you want someone who is sexually experienced because sex will not be as enjoyable if you're with someone who doesn't know how to please you and hasn't had the experience of knowing how to please somebody. On the flip side, you don't want to be with somebody who's been with a lot of, of men. They're just something about it mentally that turns a lot of men off. And I'm speaking for me,

and I may get hate mail out of this. I'm speaking through my friends as well, because, you know, we all talk about this. So I think there is a, I think there is a middle ground somewhere. And I think it's the same for women, too. I'll just say I have a lot of women friends, you know, who feel the same way. Although a lot of my women friends, and again, this is a small sample size for the nerdy people out there, this is not a P-value statistic. It's just, you know, the women friends that I have are less concerned that. They're more interested in different things. So that's just my statement. I'm a single guy. Yeah. Yeah. I mean, I think what I would say in response to that is I think on the topic of monogamy, my feeling is that I believe in the form of monogamy that is I'm going to have sex with as many

people as I want to. And ideally that number is one. That's it. Ideally, that number is one. Because when I'm satisfied, I don't eat anymore. Like, when I'm not hungry anymore, I don't eat anymore. Like, if I was in a relationship with a woman and she came home and she said, I met a guy today, I really want to have sex with. But, you know, we made this rule and I honor the rule. So we're good. I would feel terrible. That is not good.

Like, I don't want you to not have sex with other men because we agreed that that's the rule. I want you to not have sex with other men because I satisfy you sexually and you're happy with me. And you're full. You don't need anymore. You don't need to eat anymore. You're full. You're happy.

If I came home and said, oh, yeah, you know, there's a lot. Lots of women I'd really like to have sex with, but I made a promise. I'm going to honor my promise, babe. That's a terrible, terrible thing. I think it should be, yeah, of course, there's all kinds of shiny new things out there, but I love you. You make me happy. You satisfy me.

Like, we know how to get... And by the way, I'm going to push back just a little bit on... I think you're right. If someone's a virgin and they've had no sexual experience, they may have a lot to learn. The truth is, I think in every relationship we're kind of born and new. you know, we throw things from past relationships at a person in bed. But what one person liked, another person might not like, and what another person didn't like, this person might like a whole bunch.

So you learn each other. And I think that it's more important the desire to please your partner than having experience that pleasing lots of partners. Yeah, sure. If you've been driving for 20 years, you're probably better at driving than someone who just off the road. But people have been driving for 20 years and they still suck at it. And I know people that learned how to drive really quick,

and they're just good at it. They have a natural proclivity. Sleeping with me is not a metric that sleeping with you you'll be good at or sleeping with five other men successfully. Like, we're all different. We all like different things. In fact, a level of sexual experience, you might think you know something you don't know.

Because my experience of women as lovers has been that they all like lots of different things and the thing that one person likes, another person might not. And if I went into that interaction with a lot of competence based purely on experience, I'm not doing a very good job. If I'm going with a lot of confidence that I want to be good at this, and I'm going to take the time to pay attention to your body, your reaction, what gets a response from you,

I'm going to learn you, and I'm going to learn your pleasure because I want to, because I know it's important. That to me, any man or any woman would love to know that their partner feels that like. So one of the things that people discuss and ask, which is so common, I have 24-year-old. twin girls. They both have serious boyfriends. I love them both. They're both coming. We have a vacation house in Coral Lane. They're flying very long distances on

non-stop flights. You know, to be with me, I'm so grateful for them. But, you know, you think about age 24. How long is it going to be before they get engaged and they get married? There are statistics that show the longer that you date, the less lucky you are

to get divorced. But, and here's a big butt and here's a big caveat. In that same study, they had 32 as kind of the cutoff up to 32 years old. Every year you wait actually helps you stay married. The older you are when you get married, the less likely you are to get divorced. In fact, every year you wait, knocks your divorce odds down 11% up to age 32. After 32, it flips. Now every year you wait starts working against you. Your divorce odds start slowly stacking back up by about 5% a year. Is there an ideal age that people should get married?

Are these stats just bullshit? Well, those stats aren't bullshit, but the problem with all of them, I'm familiar with the studies that you're talking about, a lot of the Wake Forest studies, and there's a number of other studies that have been done that show this same thing. The problem is, again, they all gauge as the success

that you didn't divorce. And I don't think anybody gets married saying this sucked, but we managed to stay together. That's a ridiculous thing. I hate it. I kept my job for 50 years. Did you enjoy it? I hated every day of it.

Okay, then you didn't win. You lost. You gave up 50 years of your life or something that you hated? This is crazy. So all of those statistics, how likely are you to divorce? It could just be that people at or about the age of 32 learn to resign themselves to their fate and sort of acknowledge that, you know, like, yeah, I'm my own worst enemy, and, you know, happiness is sort of a temporary leading state. So, yeah, I'm not happy being married, but I wasn't happy being not married, so whatever.

It could just be that people learn to lower their expectations by that age. I really don't know how to interpret that data because unless you could then take that same sample and have some real insight as to marriage satisfaction, then I think you'd have something of value, but they don't do that. That's not because the long-term follow-up of that would be very complicated as a study. So do I think there's a lot of statistics about the likelihood of, like the most interesting statistics to me personally about marriage are a lot of the Wake Forest studies that were out there because they have a long-term institute that studies marriage satisfaction and divorce rate. It's like the center for the marriage and the family or something along those lines. And they're not like religious-based or anything like that.

They're very sort of analytical about the process. And what I think is interesting is that they've come out with a lot of studies about economics and educational factors. So people who have a college education are less likely to divorce. People who are over a certain income level are less likely to divorce, but below another income level. So that's the stuff that it's kind of an inconvenient truth that people don't like to talk about. Because a lot of my same conservative friends who are very quick to talk about a terrible, divorces, when you talk to them about, okay, so then we need to make college education more accessible to people and we need to get rid of income inequality, they're like, whoa, whoa, whoa, commie,

what are you talking about? Where, and when I say to, you know, my friends who are progressive liberals, oh, well, actually the marriage statistics for people who have children are better for, better than people who don't have children, they're like, whoa, whoa, whoa, trod wife guy. What are you trying to get women barefoot and pregnant? So, like, I can't help but piss both sides off constantly. when I point out to them that if you really cared about marriage from a statistical standpoint, that you were like, oh, we need to stave off divorce, irrespective of marriage satisfaction. Like the goal should be that people should marry and have children, whether they like it or not, to some degree.

Like whether it's going to make them happy or not, then we know what to do. Get married younger and have kids. Like, that's statistically the better way to go. But is that going to lead to satisfying outcome? the research suggests it might not. And it also, by the way, is the moment we're in. These are questions about value. Like, what is valuable to you?

You know, you just described that you have these two 24-year-old daughters who you feel a deep connection and bond with and who you love and feel pride for. You know, you have nach for them, right? Okay. If that's something that you have, well, then the marriage that you had that produced those children was incredibly successful.

Like, I'm so glad you did it. Because if at that exact moment, you hadn't been with that exact woman, you know, I was talking to my friend Andrew Huberman, and he was explaining to me like how, you know, the complicated world of sort of genetic. And he said, like, you realize if you had sex an hour later, you'd have different children. Like, you'd have different children. Like, it's really a function of, like, which sperm and which moment and which egg. And, like, it's a really amazing thing when you look at the miracle that is the existence of a human being.

If you love those girls, which of course I know you do, and you see them and you're an accomplished man, you see them as one of your greatest accomplishments, more accomplished than billions of dollars of income produced for people and hundreds of thousands of jobs you've created, you created these two lovely young women. Five kids total. I'm just using the girls as an example. I'm using the girls as an example. And also they're on the older end of the.

spectrum. So, you know, we've already seen a positive result. And seven-year-old, we're not sure. No, I'm just kidding. But the truth is we're really seeing that you produced two amazing adults, you know, and young adults on their way. And your marriage was a success. It was an absolute, I don't care that it ended in a divorce. I don't care how you feel about each other in the present day, whether you still care about each other or whether you couldn't stand each other and we couldn't put you in the same room or that you could be in the same room and enjoy each other's company. It's irrelevant. You produce these two amazing human beings. So I think we have to get our shit together, for lack of a better term, as a society, about what's the point of all of this?

Like, what's the point of the whole experiment? Because if the point of the whole thing is just maximize your pleasure, if hedonism is the goal of life, they maybe don't have kids. Because you can have lots of sex and lots of food and lots of travel and lots of other stuff. Or maybe a deep joy and fulfillment can be found in watching your children grow and have success. But there's a tremendous amount of work that you have to invest to accomplish that. That's not a like set it and forget it passive investing style, having children. Like having children is more like day trading. Like it's a lot of fly by the seat of your pants, terror.

It's like starting your own business. It's like you've got to trade what you want now for what you want most. And there's periods of time where you're like, this may not work out. and then suddenly somehow it does. And then there's moments where you go, it's definitely going to work out. And then somehow it all goes horribly wrong at that moment. It's a real long journey.

It's a hero's journey. And so I think that we have to first define what is a successful marriage before I can tell people at what age they should get married. Because if children is the goal of marriage, if children is the goal of life, if producing offspring is the most satisfying way to create your life, then we should be getting married much sooner.

and we should be creating conditions in a society where people can do that. Because it's our fault. It's us. It's us guys with gray hair. It's our fault that this is no longer the case. You can't get out of college anymore and go buy a house. You can't work for an entry-level job anymore and be able to buy. I got out of college with nothing.

And through sheer hard work, I was able to buy a small condominium, having saved a little bit every day. And I think I bought it for $140,000, something like that, and lived there with my then-wife who worked as an assistant manager at Blockbuster Video. And between the two of us, we could afford this place and put a little money away. And we invested it wisely because I called a buddy of mine and I said to him, hey, there's this bookstore on the internet. It's so cool. You can get any book. It's called Amazon. Do they have a stock yet? Because I got a $3,000 tax return. And I want to buy some stock with it so I can invest. And he said, they just posted their first earnings. They haven't really

shown anything. Like, I don't, that would be risky. Here's what you should do. If you want to take $3,000 invest, it takes $1,500 and put it in that against my advice. The other $1,500, put in a reliable known company, MCI WorldCom. And that's what I did. And that, that's been in Amazon, a bunch of years later, it bought me my next house. The MCI WorldCom, stock went down to zero. even though it was a company been around for a really, really long time, because why? The internet happened, and it got rid of all of that. So I think fundamentally, you know, what age you get married has a lot to do with. What is it you're trying to accomplish in life?

And what have we created as a society in terms of conditions for young people to get married? I have a 26-year-old who is working very hard right now. He is not in the same position I was when I was 26, and it's not his fault. We've created structural inequalities here. First wife, I have an amazing first wife. I'm so happy that we had three amazing kids, like you said. You know, my first ex-wife and soon to be second-ex-wife, very, very different. I said to my second-ex-wife, you should actually sit down with my first ex-wife

and she could teach you a lot about what it means to be respectful as a parent to do the best interest of what's in the best interest of our kids. And we'll talk about this a little bit later in the show. I want to talk about more statistics as people want to know what they actually are. And here's what they actually are. Between 46 and 53% of first marriages fail. Around 60% of second marriages fail. I'm not proud of it.

And then if you get married a third time, which I do and which I will, I'm a romantic. I love being in love. 73 to 76% of third marriages fail. Those are crazy numbers. In a lot of ways, that leads us to pre-up conversation, which you have mentioned already. I'm a romantic at heart.

And I'm wondering, Jim, so the way that a lot of prenups work, just to tell people, there's, there are clauses in there. You get married a certain amount of time. You get a certain amount of money. I know a lot of women who tell me, and I only know women who have to sign the prenups. I don't know a woman who had the money that makes the men sign the preemnity, but I do know the reverse. And the way they work, at least my friend, is for every year you get married, you get a certain amount of money. Isn't signing a pre-up with somebody on romantic? And if the man has money,

isn't it treating like your future wife like a prostitute? So those are two separate questions. So I'll take them separately. So the first one, I'll start with the second one, which is, is it treating your wife like a prostitute? I don't think so. Any more so than for a woman to marry a man and expect him to be a breadwinner

is treating him like a mule or a donkey that's there to pull your cart. I think marriage is an economy. I think economies are about people bringing value to the table. If I bring to the table that I'm a provider and a protector and I love work and I'm passionate about it and I enjoy investing and I enjoy finance and you don't and you enjoy beauty and creativity and having a home or raising children or you enjoy just being a supportive other to another person and you enjoy creative pursuits like doing yoga or making art or writing and you enjoy being a being. And you enjoy being a

there for me and you provide me tremendous value and some of that value is that we have sex and I really enjoy having sex with you because sex is really fun. Is that prostitution? I don't think so. Prostitution is I don't want to know you. I'm paying you to leave if you're a prostitute. I'm not paying you to have sex with me. I'm plenty of people have sex with me. I want to have no emotional tie to you whatsoever and you'll have a particularly unselfconscious kind of sex with me in exchange for me giving you money and then you'll leave and I don't even have to talk to. if I don't want to, or I can talk to you for as long as I want, and then I can, okay, you got to leave now. It's the thing. And again, is that undignified? I don't know. Is it undignified for a person to do a job

that they hate all day long for many, many hours just in exchange for a certain amount of money because they need it to feed their family? I don't know if that's undignified. I think we all make compromises and do things for the purposes of having resource scarcity and dealing with resource scarcity. So I think all of that is an economy. Is a pre-nup unromantic? I don't think it's unromantic at all, I think there's something extremely romantic about a pre-up. Because I think a pre-up is about saying to someone that you can't feel loved if you don't feel safe. And I can say that unequivocally, because I represent victims of domestic violence and intimate partner abuse, and I have for many years. And I represent people who don't feel safe in their relationship, emotionally safe, financially safe, whatever it might be. You know, love is about intimacy. And intimacy is defined as the ability to be completely yourself. with another person and to be vulnerable with another person and to show them your soft, weak spots, the things you're afraid of, the things you need to work on so they can truly love you and you can truly feel their love. So to me, you're giving someone a gun to shoot you with, essentially.

You're saying, I'm going to show you all the things I'm afraid of. I'm going to show you all the things that matter to me, all the ways that people have hurt me. I'm going to share them with you in an unfrightened and unreserved way. But you could use that to hurt me terribly. So how can we feel safe with each other? And I think there's something very romantic to me about truth. Truth is beautiful. Truth sounds different. You know, when someone speaks to me with honesty and vulnerability,

it's the most beautiful thing. When someone says, you know, hey, I'm really sorry I did that thing. I'm like, okay, I can accept an apology. But somebody says to me, you know, I'm really sorry I did that. You know why I did it? I was really scared and I really was being a little nervous. Now I get it, man, because I felt all those emotions too. I'm human just like you.

That's beautiful that you could say to me why you did this thing that hurt me. It helps me understand that you didn't do it because you don't like me or you're like, it shows me like, oh, you're human and I'm human too and that's beautiful. So I think there's something really beautiful about the conversation about a pre-nup. How can you feel safe? You're safe. A woman married me and she has limited resources. And she says to me, listen, I don't have as much money as you.

You have lots of money. And I find that very appealing. not only because money provides security and experiences for us, but also because the money says something about you. It says that you're someone who knows how to be focused and discipline and trade what you want now for what you want most. It shows me that you have tenacity, and you'll bring that same tenacity to this relationship.

And I'm really excited about that. That sounds fun to me to be with someone who's so passionate and so dedicated. That sounds like a great thing. And I say to her, yeah, and you know, I love that you're beautiful. I love that you have, like, beauty. By the way, that beauty says something. It says something about how you want to present yourself. to me like an offering and how I'm important to you and I have value.

And it also tells me something about a level of to be beautiful and to be in good shape and you have to have discipline. You have to trade what you want now for what you want. Most of the same traits that we just talked about. You know, entrepreneurship and financial success is not the only marker of passion and discipline. You know, there's lots of markers of those things. That's why I always say, like, I like people that are in shape, not because like muscles

are particularly good or a woman being particularly thin is important to me. That's not. I don't actually particularly find very thin women. attractive personally. But I do think there is something about the habits and the discipline that it takes to go to the gym and to have an exercise regimen and to eat in a healthy manner. I think there's really value in showing me that you'll trade what you want now for what you want most. So I think pre-ups can be a conversation about what are you scared of and how can I help you feel less scared? Can we share with each other what we're afraid of? Because here's the

thing. That's a really useful conversation. If you just show up in your next marriage and you say, listen, I had a lot of resources when we met. So I want you to sign this pre-up. It says that you get nothing. Don't marry that guy because he doesn't really care about your needs. He doesn't really care about your fears. If a future wife says to you, listen, I really want to marry you and I want to make you a huge priority in my life. I've done the work thing and I'm not as into it as you are. Or I've never really been great at the work thing. I'm not interested in that. That doesn't turn me on and excite me the way that being a supportive other makes me excited. Okay, cool. You like that. You're in. Okay. If that's, again, if that's your flavor, it's my flavor, it's your flavor great. But here's my

fear. I'm afraid that in the future, I will have invested a tremendous amount in this relationship time, my beautiful years, these years where I'm young and vibrant. And I'm afraid that after a period of time, you'll just walk away. And I won't have enough to take care of I would not hear that and go, of course, that's a reasonable thing to be afraid of. It's certainly more reasonable than you being afraid of sharks. You know, like the chances of you getting bit by a shark versus the chances of a successful man who's been married twice getting divorced a third time. You said it's in the 70% like totally much higher that I haven't checked the shark attack statistics.

But I don't think there's anything wrong. I think there's something beautiful about saying, hey, I'm scared. tried this twice and it didn't work out but man i want it to like i want it to so bad and you know what i'll i've learned each step of the way i think i think i'm getting better at this man i want to get better at this if we can figure out together how to get better at this and stay better at this i'm in i'll do the work like you've proven you're a man will do the work in the boardroom in the gym you do the work so i'll do the work on this thing. Yeah, I didn't get it right the first two times. Okay, I know a lot of people that tried to start a business and failed the first two times and then created Fortune 500 companies.

So bullshit that you didn't do it before, it means you won't do it the next time. I don't think that's true at all. But I don't think ignoring your failure is not learning anything from them is useful. And I don't think pretending, like, well, let's just on a wing in a prayer, like this time it'll work. Like, let's, what did I get wrong last time? What could I have done better? By the way, you were a different person. 25 years ago, you were a different person, for God's sake. You know, you're not, the technology that worked or didn't work

25 years ago in your marriage, you don't have to worry about that. We live in a different world right now, and you're a different person than you were. But do you want to be good at this? A pre-up is about, I'm going to bravely tell you what I'm afraid of, and I want you to bravely tell me what you're afraid of, and I want us to find a way for each other to feel safe in this relationship. And then I want us to both remember what is this thing the other person's afraid of? So when we start bumping into it in the relationship, well, no,

oh, I'm bumping into that thing he was afraid of. And I love him enough that I'm going to realize when I'm doing that and I'm going to figure out a way to reassure this person. That's beautiful, man. I'm a romantic at heart too. There's nothing more romantic to me than that than two people bravely telling a other what they're afraid of and saying, okay, I want you to feel safe, even if the thing you're afraid of is me, you know, I want you to run to me if somebody hurts you, even if that's somebody's

me. I think there's a little bit of a misconception out there about how a pre-nup actually happens. Someone asks the other for pre-nup. You have to be independently represented by counsel. You can't jam it down someone's throw right before a marriage. A judge will say, no go. It's not valid. I think a lot of people think, okay, you know what? Pre-up, no person. We're getting divorced. Here's what the paper says. No problem. We don't have to fight about anything, but every single person, Jim, I know is a pre-up is still a war. Is a pre-nup really that helpful at the end of the day? Yeah, pre-ups are very helpful for the things they're helpful for. But the problem is, just because, like, that's kind of like saying, you know, I know people who've been sick

and antibiotics didn't help them. So do antibiotics even work? It's like, yeah, if you have an infection. like if you have a virus, antibiotics aren't going to do shit. You can use as many of them as you want to. It's not going to accomplish anything. So like I get this a lot from people because they'll say, oh, well, you know, pre-ups. Like, I have a buddy and the pre-nup,

he still was in court for 10 years. He was arguing about custody, child support, visitation. You can't bind those things with a pre-up. Those things aren't covered in a pre-nup. But here's what will make a divorce worse. Don't address the things you could address in a pre-nup. Spousal support, alimony. division of assets separate property versus marital property estate and inheritance rights if you just did a pre-up that

said all my business interests i owned at the time we got married remained my sole in separate property and it bound nothing else you just saved a couple of hundred thousand dollars if you get divorced done done short little pre-up not complex going to stand up in all 50 states piece of cake but to say but i still might fight about custody, so why even get a pre-up? That's crazy. That's like saying, you know, people still get in car accidents, so why should I even have an airbag? Well, because it's going to minimize how bad the impact is. And by the way, it might keep in your line of sight that, hey, this is a dangerous activity I'm engaged in. I should actually be conscious and not texting while I'm driving. Like, there is value in having a pre-up. Yes, is a pre-up a panacea, a cure for every ailment

that could possibly be? No, no. You could still end up having an ugly. divorce with a pre-up. But it's not going to be over the things that are covered by the pre-up. Pre-ups stand up. Pre-ups are well-tested, well-settled law. If they are drafted correctly, if you spit it into an AI large language model and think that you're going to save yourself $500, yeah, you're right. It probably won't stand up in a court of law. If you present it to your partner as they're walking into the wedding venue, yeah, it's probably not going to stand up. But the people that come in and they go, you know, exercise the person, doesn't work because the guy who wrote the complete book of running Jim Fix, he died while jogging.

So that's just proof that jogging's not good for you. Okay, that guy outlived every one of his other male relatives because he had congenital heart disease of a very high level. And by the way, that's a singular person. You're going to base all of that on. Look at the statistics. Exercise is good for you. It decreases your risk of heart disease, period. End of story. That science is settled. So to say, well, I know a guy who exercise. I know someone who smoked and they were 100 years old. so therefore smoking can't be bad for you. That's preposterous. There are all these outlier people that say, oh, yes, my pre-nup did. I have been in the trenches defending pre-ups and challenging pre-ups, and I am a very good lawyer. There aren't a lot of things I have the right to say I'm good at. I don't know if I'm a good lover. I don't know if I'm a good father. I don't know if I'm a good employer. I've proven that time and time again. I have a number of times tried to set aside pre-ups unsuccessfully. Believe me, it is a part. hard, hard thing to do. My stats on defending prenups are through the roof. My stats on getting them set aside are like every other lawyers, abysmally bad, low, because their contracts and

contracts are binding.