“Nobody knows the dark side of marriage like a divorce lawyer, and James Sexton is a good one. In this engaging, wry, and illuminating book, Sexton shares his legal war stories and dispenses some no-nonsense relationship advice for anybody thinking about getting married or hoping to stay that way. It’s an entertaining dose of tough love from a man who knows what he’s talking about.”
—Tom Perrotta, author of Little Children and Mrs. Fletcher
“Divorce is common, obviously, but how many people make the logical projection that seeds of thousands of future divorces are being planted and nurtured right now? How many couples recognize themselves as the misery farmers? While there’s still time to stop themselves? James J. Sexton has a useful vantage point, blunt advice, and enough grisly stories to make self-help entertaining—unless, I suppose, the marriage he’s describing is yours.”
—Carolyn Hax, nationally syndicated advice columnist for TheWashingtonPost
“Here are three things I did while I read this book: laughed, cringed, and scribbled a whole slew of notes in the margins. . . . James Sexton delivers frank, no-holds-barred advice, gleaned from the front lines of divorce. The real trick, though, is how he does it with so much love. . . . This is a book teeming with hope.”
—Grant Ginder, author of ThePeopleWeHateattheWedding
“Wryly written with plenty of candid wit and straightforward opinions . . . Sexton’s enthusiasm and affinity for marriage stories is evident throughout as he examines issues such as honesty, sex negotiations, infidelity, long-term relationship ‘slippage,’ and that stinging realization that ‘what’s fun when you’re dating is a pain in the ass when you’re married’ . . . sage counsel to help readers better navigate the trajectories of their own relationships.”
Kirkus Reviews
“James J. Sexton’s book is a delightful surprise. Sexton is not offering the usual how-to-have-a-happy-marriage book, but rather a how-notto-divorce book. . . . Sexton doesn’t judge. People fall in love, then life interferes and marriages dissolve. And when they do, you want a cleareyed lawyer in your corner. However, perhaps reading his book could avoid that meeting.”
TheStar-Ledger
“Who would have guessed that the person who gives the best advice about marriage was the guy responsible for getting you out of yours?”
—Judith Newman, New York Times Book Review
“As a trial lawyer, James, for over two decades, has negotiated and litigated a huge number of high conflict divorces. This has given him a deep understanding of how relationships fail and how they can succeed, and bigger than that, the role of love and pain in this whole messy rollercoaster ride we call life.”
—Lex Fridman
“James J. Sexton has spent nearly 20 years handling custody disputes, childcare payments, prenups and postnups, and basically every conceivable divorce scenario. His new book is a distillation of the lessons he’s gleaned along the way.”
HOW NOT TO F*CK UP YOUR MARRIAGE
HOW NOT TO F*CK UP YOUR MARRIAGE
Straight talk from a divorce lawyer who’s seen it all
JAMES J. SEXTON
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For
Mom, Casey, and Nate “The Great”
Everything in this book is factual. Names and identifying details have been changed to preserve my license to practice law.
When I first wrote this book, I had no idea it would resonate so deeply with readers all over the world. Why would anyone be interested in what a divorced divorce lawyer has to say about keeping your relationship together? I thought, on paper, I was an unlikely source of wisdom on how to stay in love.
However, over the last few years, I’ve been thrilled that people have found something of real value in my perspective. In candor, the first time a clip of one of my interviews hit 100 million views, I was left scratching my head. What exactly made my point of view so interesting? I couldn’t quite put my finger on it. We don’t know who discovered water but it was unlikely to have been a fish.
I’ve been a divorce lawyer for twenty-five years, so I think it’s safe to say I’ve seen every permutation of heartbreak. I’ve advocated, in court, for each side of every possible family law issue. I’ve represented the accused and the accuser. I’ve represented the villain and the victim. I’ve represented people who are great parents and people who, by all possible metrics, are atrocious parents.
And I’ve discovered something about myself through these moments. Want to know what it is? The truth is, I’m very sensitive.
I’d appreciate it if you could keep that between us. I’ve been
described as a “courtroom gunslinger” and “the sociopath you want on your side”, so it would be bad for my brand if people knew otherwise.
However, you can’t do this job well unless you’re sensitive.
In a courtroom and at the negotiating table you need to put yourself in the mind of everyone involved in the case. What are they afraid of? Who are they and who do they want people to think they are? What do they say they want, and might it differ from what they really want? Being sensitive, I’ve realised, is a superpower as a divorce lawyer; it allows you to cut through the crap and see past the bullshit we tell ourselves every day and portray to the world.
That superpower has never been so important. In our increasingly performative society, every moment is another opportunity to convince the world, on social media, how happy, successful, and in love we are. We are inundated, every day, with images from the “greatest hits” of relationships around us—all while we live our personal “gag reels”. There’s a growing skepticism in the world as the divide grows between people’s heavily filtered public lives and their real lives and relationships. We are drowning, as a culture, in a sea of curated bullshit.
In recent years I’ve been asked to share my insights on some of the world’s biggest podcasts and in viral TikTok clips. To preserve my sanity, I try not to read the comments, but on the rare occasions where my curiosity gets the better of me, I frequently see some variation of the same general idea: “This guy is so real!” and “He’s saying facts.”
Comments of that kind have now started to make sense to me. You may not like some of what I have to say about love and marriage, but it’s born of direct observation from a unique vantage point. People lie about their relationships constantly. They lie to themselves. They lie to their spouses and partners. They lie to their family and friends. They even lie to their therapists.
People rarely lie to their divorce lawyer.
The first edition of this book was published in 2018. That’s the same year ByteDance, the company that owned Douyin, a short-form video app, acquired Musical.ly and rebranded it for a global audience as TikTok. As the years pass, it’s increasingly undeniable that it was a
big moment for social media but the start of some very dark times for romantic relationships.
When I first wrote this book, social media (primarily Facebook) was already reshaping the way we met, loved and eventually left romantic partners. Today, the impact of social media is global and inescapable. Platforms like TikTok and Instagram have made connection easier, but distraction and betrayal easier, too. Couples no longer argue exclusively about “traditional” infidelity but over “emotional cheating” through DM’s and secret social media accounts. While adultery was likely the next invention to be made after the concept of monogamy, there’s no denying we are all, at this moment, learning how to navigate even more novel forms of distraction and betrayal.
My mentor at NYU, Dr. Neil Postman, once commented to me that technology offers us “real solutions to imaginary problems and imaginary solutions to real problems”. He was quick to follow that up by echoing Wittgenstein’s view that technology is, ultimately, “an improved means to an unimproved end”.
Indeed, I’ve represented celebrities, elite athletes, C-Suite executives with Fortune 500 companies, world-renowned surgeons and some of the most talented financial minds working on Wall Street. These are people who literally shape the world we live in; people who have achieved nothing short of mastery in art, sport, business, and technology.
Do you want to know another secret?
These people find love as challenging as you do.
Our cultural and technological landscape changes constantly but the biggest issues I see in marriages are still the same ones I saw two decades ago when I started my career as a divorce lawyer. So, if you’re picking up this book for the first time, I hope it helps you avoid the mistakes I see in my office every day. If it doesn’t help you avoid those mistakes, I hope it gives you some comfort to know that some of the most brilliant and talented people in the world share your ineptitude in this aspect of life.
I’ve tried, in this book, to offer you the insight on keeping things
together that I’ve learned by watching things fall apart. It’s practical, sometimes uncomfortable, but always honest advice from someone who has seen, over and over again, what happens when love goes wrong.
Falling feels like flying, for a little while—until you hit the ground.
The now-thrice-divorced Jennifer Lopez told us in one of her hit songs that “love don’t cost a thing”, but I’ve learned it’s a bit like dining out: you have to wait until the end for the bill to come. I’ve spent so much time around heartbreak you might, understandably, think it would make me cynical about love.
You would be wrong.
We break in relationships. We heal in relationships.
I’ve had a ringside seat to the brutality and sadness that often accompanies heartbreak. And I’m still most fascinated by the way we, by overwhelmingly large margins, never let those break-ups cause us to give up on the possibility that we might still, someday, find and keep love.
There’s something strangely beautiful about how bad we are at love—and how we never stop trying anyway.
I hope you find something in these pages that helps.
James J. Sexton, Esq. New York City, 2025
INTRODUCTION
Take the Path They Didn’t
This is a how- not-to book.
How not to fuck up a good relationship or marriage.
In short, the goal of this book is to keep you out of my office. Better still, the goal is to help you have a marriage in which the idea of coming to my office would only ever be the most momentary of fantasies when your spouse does something boneheaded.
If you’re not married, the goal of this book is to keep you from heading toward the mistakes and bad choices that my clients and their romantic partners have made that brought someone like me into their lives.
As a divorce lawyer who has facilitated the demise of more than one thousand unhappy marriages (and counting), I observe the things people typically do to ruin their relationships, to stifle their happiness and that of the person whose well-being they once cared so much about. Year by year, couple by couple, I can’t help but take it in. I’m not a therapist, but almost every day at work, women and men describe to me, in total candor and painful detail, all the behaviors that they or their partners engaged in to turn a relationship born of the best intentions into a steaming pile of shit. The miscommunication, the noncommunication, the deluded communication, the self-absorbedness, the changing when stability was called for, the not changing when evolving was
called for . . . I’ve had a ringside seat to countless ruined or doomedfrom-the-start relationships.
After two decades of performing this profoundly intimate service for so many ex-spouses-to-be, as well as for people in myriad other relationship permutations (e.g., living together; having a child in common), the sheer bulk of these observations has turned into a wisdom of sorts. Not long ago— about the time my own marriage was dissolving—I started to think that there was practical value in sharing what I had learned; that people in marriages and other romantic relationships who really want things to work in the long term might be at least as well served by the not-to’s as by the words of those who claim to know the “secret” of creating a “strong” or “good” relationship, those mystical truths that fill so many magazines and books.*
Let me say right here: In my practice, I have not gained insight into what makes a relationship “good,” and I won’t really opine on the subject. It may be, quite simply, that from where I’m sitting, there appear to be countless ways that something can be good but a finite and more easily identifiable set of ways things go bad. In my professional life, I do not see the good marriages, the great marriages, the solidly pretty okay marriages. The people in those marriages never set foot in my office.
I know that—just as an oncologist is aware that not everybody has cancer, though everyone who comes to see him does.
No, everybody is not fucking everybody. (Most divorce lawyers adopt this dark worldview pretty quickly.) No, not everyone is cheating their spouse out of money or trying to use the kids as leverage to minimize child support obligations. I am guessing— though I believe this is an educated guess— that in the good relationships, the ones I don’t see, many of the recommendations I make throughout this book are already in use, resulting in incredibly rewarding, enduring unions. I know this: In twenty years of practice, I have never—not once, not ever—met a person who was cheating on their spouse and who also appeared genuinely in love with that spouse. I have never met a happily married
* As a divorce lawyer who got divorced, I have learned at least as much about love and honesty from the latter condition as from the former.
person—not once—who was involved in massive financial impropriety. If you know you’ve got something special, you don’t out of nowhere start behaving in ways to jeopardize that.
But do you really want insights into love and romance and successful partnership from a divorce lawyer? Yes, and here’s why: The therapists and women’s magazines and television and radio “experts” who claim to offer the keys to a great relationship have shared them for decades— and somehow my business and that of my colleagues is still booming. If there’s a shortcut to the happy marriage, somebody would have found it by now.
Maybe we need a different approach to the challenges of marriage, commitment, long-term happiness, monogamy, and the rest. Because as a species we certainly seem to suck at it. Maybe if we focus on how we break things, we can figure out how to keep them from breaking.
I did not set out to write a how-not-to book. My original aim was to give a candid, witheringly honest look into the world and perspective of a divorce lawyer, especially the parts of that world that most people don’t normally see and hear, much as Anthony Bourdain showed us what being a chef is really about. Not the make-believe. I didn’t want to hold anything back.
The more I wrote, though, the more I realized that there was utility, not just drama, in the unique view I had of relationships:
• Virtually all the unions I see are damaged beyond repair.
• I have heard the stories of these relationships in their entirety, from promising beginning to unhappy end.
• I am given virtually unprecedented access to even the tiniest details of these stories. (In many ways, I am privy to more of a person’s true life than any therapist: I am told what you tell your therapist + your accountant + your best friend + your fi nancial advisor + your parole officer + your spiritual leader + [if you’re a parent] your child’s school guidance counselor or shrink.)
• I am tasked with an act of reparation/improvement that demands yet more brutal honesty (if I am to help my client build the best next steps).
I thought, Why not leverage what I’ve learned to provide value for the many, many people who will never set foot in an of ce like mine? I was motivated to do this for two reasons, the second of which you’ll laugh at: One, I’m a realist and, two, I’m a romantic. (I am. I’ll explain more in Chapter 1.) A new book emerged, though it still includes just as many of the revealing (and, I hope, entertaining) details of the life of a divorce lawyer.
I have not watered things down. As I just wrote, I’m a realist. Show me a divorce lawyer who is not a realist, and I’ll show you someone who is no longer a divorce lawyer.
What I say may sometimes sound pugnacious, nihilistic, perhaps offensive. I believe it takes great courage and hard work to make a relationship last, and to make a good relationship even better. I believe it’s preferable to confront what may not be working so that you can make your strong marriage or relationship stronger (or yourself stronger). I believe this is far better than the illusory comfort provided by not confronting issues, pretending there are none, and letting that denial gradually and inevitably drag things down, then trying to yank the relationship back up to where it had been. I believe in living in the real world. A friend once emailed me a clip of an episode of Real Housewives of Some American City, and one of the wives, to prove how solid and secure and “divorce-proof” her marriage was, boasted that, “In our house, we don’t use the D-word.” My honest opinion? That’s just fucking stupid. The existence of divorce is out there whether you acknowledge it or not. I may decide we won’t “use the C-word” in our house, but it doesn’t mean no one’s getting cancer.
I’m not so arrogant (some who know me may take issue with that assessment) as to believe that following the advice in this book will turn a bad relationship into a good one. Nor is this book just about steering (more) clear of divorce. It’s about life outlook. It’s not so much “I don’t
want you to divorce me” but “I want you to be happily married to me.” Those are two totally different ideas. You’re not interested in whiteknuckling it through until death does one of you part. You’re interested in having the best, most mutually enriching, joy-filled, good-sex-filled life with someone who wants to stay married to you. A marriage that makes you both better people, on a continuing basis. Isn’t that what you signed up for, or thought you had?
It’s not even about marriage. It’s about meaningful connection. That’s something I learn over and over and over. Ask most people to name the two top reasons for divorce, and they’ll almost always guess correctly: cheating and ruinous money issues. But those are never the reasons for divorce—rather, they’re the symptoms of a bad marriage. Lack of meaningful connection and proper attention and enduring affection led to those lapses, not the fact that someone in Accounts Payable happened to be wearing an incredible outfit one day when the weather turned warm. (Damn you, Heather!)
As the title suggest, this is a how-not-to. How not to stifle your happiness. How not to stifle your partner’s. How not to sabotage the connection that made you want to get into a romantic relationship to begin with. How not to fuck things up. If you think you see occasional contradictions in the advice that follows, you’re right. Marriage is full of contradictions. Same with love. Same with life. But there are some basic truths that can’t be contradicted, some actions you can absolutely take. The pillars. If I enunciated them in five or six bumper stickers, though, I wouldn’t have a book. I’d have five or six crappy bumper stickers. And you’d still have a relationship that’s not as fulfilling as it could be. My profession has made me pragmatic, but it hasn’t taken away my faith in the power of love. If anything, it has shown me how deeply we all yearn for connection and romance. I never set out to learn what makes a relationship strong. But I have witnessed, up close and always personal, what makes it weak. No single raindrop is responsible for the flood. But if you look hard enough, you can reverse engineer, pretty easily, how the flood came, and when the first drops started falling.
Let’s try to find, and keep, some clear blue skies.
HOW NOT TO F*CK UP YOUR MARRIAGE
Chapter 1
WHAT IS THE PROBLEM TO WHICH MARRIAGE IS THE SOLUTION?
If you’ve thought long and hard about what marriage means, congratulations: You’re different from many of my clients. (That may be one reason they’re not still married.) I’m forced by professional necessity to think deeply about marriage. I get to analyze it, though in its broken, Humpty-Dumpty-after-the-fall form, from so many angles— the psychological/emotional, the sexual, the fi nancial, the parental, the practical/logistical. If we can stand back for a moment from an institution so rich with powerful associations—many very good, some not so good—it’s helpful to recognize that marriage is a technology. Like every technology, or tool, it solves certain problems, intentionally, and creates new problems, unintentionally.
What is the problem to which marriage is the solution? Take a minute to think about it. Or three. Is it the problem of being alone? Nope. You can find ways to not be alone without being married, nor does being married solve the problem of loneliness all the time, or for many people, even most of the time.
Does marriage solve the problem of being uncommitted to anyone? No; you can feel committed to people and not be married. You’re certainly committed to your children, your biological parents, your coworkers, your religious community, even your softball or cricket team (bonus points if it’s a team associated with your religious community).
What about the problem of not getting enough regular sex? Come on. Sex is everywhere. From Tinder to Grindr to Hinge, it’s in the palm of our hands anytime we want it (no pun intended). And countless married people will tell you that marriage is not, in fact, the solution to the problem of not having a satisfying sex life. Rather, it’s often the primary cause. Being married doesn’t guarantee a regularly accessible, satisfying sex partner any more than living near a restaurant guarantees being well-fed.
No matter how much you love love, if you want to stay in a marriage or long-term commitment and, more important, if you want to keep it vital, you’re strongly advised to acknowledge that the relationship solves certain problems while causing others. What problems does it inadvertently create? Lots of people, including many of my clients, were or are reluctant even to ask this question. Or maybe they asked it but, confronted with the answer, failed to do anything about it.
This appeal to be clinical may seem jarring. After all, marriage is the triumph of faith over reason. That’s not just a divorce lawyer talking— I mean, look at the statistics: 56 percent of American marriages end in divorce. (The divorce rate for first marriages is a bit under 50 percent; with each subsequent marriage, the divorce rate increases, hence the over-50-percent total.) Let’s say another 5 percent hang on for the kids’ sake. (The percentage is considerably higher than that, but let’s say 5.) Say another 5 percent hold on for religious reasons. (Eternal damnation is a terrifying, powerful incentive!) Say 2 percent hang in just because the sex is still phenomenal, though nothing else is. We’re up to 68 percent of marriages that either end because of unhappiness or continue unhappily. Two in three. If I told you that when you walk out the door there’s a two in three chance you’ll get hit by a falling bowling ball, would you ever leave the house? Would you at least wear a helmet? In 2010, Toyota discovered a .003 percent failure rate on a vehicle they produced with certain brake pads; the company immediately recalled the vehicle as unsafe. So here’s an institution that fails roughly 70 percent of the time, yet remains a legal, wildly popular endeavor and multibilliondollar-per-year industry, regardless of the massive financial and emotional
costs of failure. As a divorce lawyer, you sometimes ask yourself, Is any married person happy? Is anyone happy in a committed, long-term, nonplatonic relationship? (Yes, they are. I don’t want you to think I believe it’s an enterprise doomed to fail from the start.) Given a divorce rate of 50-plus percent, meaning the two people strolling down the aisle are “more likely than not” (a legal term) to someday end up in a matrimonial law office, and given that divorce almost always causes profound harm to the parties and their infant issue (kids), one could reasonably argue that the act of getting married is legally negligent! If you think the US is simply an anomaly, the divorce rate in the UK is well above 40%, and Australia is only slightly lower.
Okay, that’s depressing—but it’s the preamble. Now for the encouraging part. While divorcing parties are generally not inclined to work at making things better for their partner— often to their own detriment, too— those in decent marriages or relationships are motivated precisely to do so. Both parties can and probably will work toward improving and deepening the relationship, so long as they identify what needs improving and they carve a clear path to doing so. Because it’s better to stay in love, to stoke existing love, than to slowly fall out of love and try to find it again. The process is something that you control, and that the person you love controls. How great is that? My incredibly astute former office manager, Annmarie, believes that the marriage contract should be renegotiated every seven years. Agree with her or not, the idea shines a light on the need to stay conscious and motivated and excited, on a very regular basis, about this unbelievably important, consuming relationship to which you’re committed. I can’t count how many times I’ve heard some version of this sentiment from clients, particularly wives who were cheated on: “But I was perfectly happy with our miserable life!”
So that you don’t think my work has totally jaded me: I’m a romantic. Don’t laugh. I get misty-eyed at weddings, every time, during the ceremony and the toasts. (I don’t bother to dissuade those sitting next to me who assume I’m tearing up at the prospect of future business.) How do you not get choked up looking at the two of them up there, as public and operatic as can be, staring at each other unbroken for so
long? The moment the bride appears, I always look to the groom, whom almost no one is watching. This is (supposedly) the first instant he’s seeing her in her wedding gown. At that moment, he’s more in love with her than anyone is in love with anyone else in that big room. Every wedding I go to, I want so badly for it to work for those two.
Whenever I help to facilitate the demise of an especially long-standing marriage, there’s a moment, usually right before the final dissolution, when I am overcome by a desperate urge to see the wedding album. I want to climb up to their attic or open their closet, dig out the album in its cardboard box in the corner, dust it off, and make my way slowly through its pages. I want to see my client and their ex when they were completely in love and nothing mattered but each other. When the idea of “grounds” and “alienation of affection” and “interlocutory order” and “grandparent visitation” and “community property” and “irretrievable breakdown” and a litany of depressing Latin terms would have been laughable, unimaginable, so “Not us!” When the parties’ “infant issue” or “the child of the marriage” (as I call them in written pleadings) was just yellow-highlighted possibilities in a book of baby names. I want to see the faces of the newlyweds on that day, one image after another, in mutual bliss. (Maybe I want it so badly, have always wanted it so badly, because as kids, my sister and I were forbidden to look at our parents’ wedding album: If we did, Dad, a former pilot in Vietnam, would start to cry, because so many of the groomsmen and other young men in the photos, buddies from the Naval Academy who also became pilots in Vietnam, were dead.)
I want to see that album because inside so many bad marriages is something good and hopeful that, at one time, was absolutely salvageable.
I’ll be candid: I’m secretly a pretty sensitive soul. I love puppies. I adore my kids. I love courtship and holding hands and music and sunsets and Russian poetry. Dammit, I’ve seen Love Actually fifteen times. I love love.
