About this episode
James Sexton is a New York-based divorce attorney and author, known for his expertise in family law and insights on marriage and divorce. What does it actually take to avoid divorce? In a world where most marriages don’t last, it’s easy to assume you’ll be the exception, until reality hits. So how do you prepare for a great marriage… and, if things don’t work out, make sure you’re equipped to handle a clean separation? Expect to learn what kind of marriages athletes and actors mostly have, the most difficult profession to navigate divorce with, the worst marriage advice to give someone, how prenups actually work, how to set your relationships up for success at the start, how to argue well as a couple, how to know when it's time to quit and much more… Timestamps: (0:00) Why Pro Athletes Make the Worst Divorce Clients (8:45) The Most Misunderstood Truths of Prenups (16:46) Do You Actually Need a Prenup? (25:43) Why Avoiding Hard Conversations Ruins Relationships (38:39) What Healthy Disagreement Looks Like (47:51) How to Set a Relationship Up for Success (53:55) Will Men Do Anything For Sex? (01:00:00) How to Help Your Partner Level Up (01:17:46) The Biggest Sign It’s Time to Leave a Relationship (01:31:08) How Children Shape Your Relationship Decisions (01:40:13) The Right (and Wrong) Way to Get Over Someone (01:51:56) Why Real Love Goes Deeper Than Appearances (01:56:31) Where to Find James Sponsors: Get my free Valentine’s Review with 75 life-changing questions to ask your partner: https://chriswillx.com/valentines See discounts for all the products I use and recommend: https://chriswillx.com/deals Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom New pricing since recording: Function is now just $365, plus get $25 off at https://functionhealth.com/modernwisdom Get a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom Sign up for a one-dollar-per-month trial period from Shopify at https://shopify.com/modernwisdom Extra Stuff: Get my free reading list of 100 books to read before you die: https://chriswillx.com/books Try my productivity energy drink Neutonic: https://neutonic.com/modernwisdom Episodes You Might Enjoy: #577 - David Goggins - This Is How To Master Your Life: lnkfi.re/SN-Goggins #712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: lnkfi.re/SN-Peterson #700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: lnkfi.re/SN-Huberm - Get In Touch: Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx YouTube: https://www.youtube.com/modernwisdompodcast Email: https://chriswillx.com/contact - Learn more about your ad choices. Visit megaphone.fm/adchoices
Episode summary
Valentine’s Day is adorable and professionally chaotic; love is in the air, proposals are everywhere, and I can already see which of today’s bold choices will walk into my office down the line.
What patterns do you see in marriages and divorces for pro athletes?
Elite athletes live like monks for one craft, which can help in marriage, but career shape matters; NFL players often marry young, earn huge money fast, skip prenups, and then crash into identity loss when the short career ends, while longer‑tenure leagues face a gentler slope.
I’ve seen estimates near seventy percent divorce for pro athletes, with about half happening within a year of retirement.
Retirement replaces a regimented life with silence and too much freedom; without support, restlessness turns inward and then onto partners, so tiny quirks start to feel like big betrayals because you’re unhappy with yourself.
Who’s toughest to face on the other side of a divorce?
In New York, aggressive finance types love risk and want to roll the dice in court; most divorces need a scalpel, but my lane is the sledgehammer for when someone comes hard and the courtroom becomes the great equalizer.
People don’t get prenups: every marriage already has one—either the state’s default rules or an agreement you two design—yet we invite the government in without even a brochure about how legally huge marriage is.
Every state has oddities, like looser hearsay for child‑services reports in New York or archaic bans on consensual acts, which launched us into an unplanned, highly spirited hand‑versus‑mouth bit that probably peaked with a Papa John’s callback.
I still say there’s a case for bringing back the classics.
If you need a third party for that, we’ve lost the plot, but point taken.
Do prenups correlate with divorce risk?
There’s no clean dataset, but after decades of doing hundreds of prenups, very few of those couples ever return for a split with me; my hunch is the candid, brave talks you must have to sign one make breakups less likely, though some couples do split in the process.
When should someone raise it?
Early—third date isn’t crazy; float it through pop‑culture chatter, then fold it into real life questions like kids, pets, geography, and family, because love requires safety, and a prenup is two people designing safety for each other, especially where one partner pauses a career and loses earning power.
How do you pitch it without killing romance?
Normalize it as choosing your own rulebook while goodwill is high; I love you enough to protect you, even from future me, so tell me what would help you feel safe and I’ll do the same.
Are in‑marriage behavior agreements becoming common?
More people try them, but enforcement is tricky; better to treat marriage like an economy of value and aim for fairness over sameness so strengths can shine without scorekeeping.
Does writing rules up front box you in later?
Set a baseline, not a cage; the twin mistakes are thinking marriage will fix someone or freeze them, so track changes together—yes, even how often you’re intimate—and notice drift before resentment builds; also, fine, pizza and a throwback hand job might count as cardio.
I’m seeing more couples talk transparently from the start; the lows, not the highs, decide the future.
Totally; paradise dates prove nothing—stress does—and real romance is letting someone see the messy parts you fear make you unlovable, then being chosen anyway.
If the lows matter most, how do you fight well?
Argue about the real issue, not the dish in the sink; never turn shared vulnerabilities into ammunition, and agree on fight rules in advance so you both know how to step back from the ledge.
Attachment science suggests cooling things within a few minutes so it doesn’t encode as threat.
Speed can trigger defenses; I like a “hit send now” email you both recognize as a thoughtful de‑escalation, plus positive framing in the bedroom—invite, don’t indict.
I love asking couples how they met.
It melts tension fast by returning you to the spark when you felt interesting to each other.
What sets up a new relationship for success?
Keep talking, even about how you’re talking; use good question decks and enjoy the slow reveal instead of sprinting past discovery.
Men wire in with rewards; praise and clear targets pull us toward effort.
Challenge fuels me too; courtship standards and paced novelty help everyone, and if I know your underwear color but not your siblings, we’re out of order.
Women set the standards, men rise to meet them—or sink when the bar is low.
From the divorce trenches, I agree; men need a code and should signal seriousness, women are the gatekeepers, and the mission is self‑mastery over shortcuts.
Even talking about this draws fire, which is why a softer, saner lane for men has been emerging.
Call us gentlemen, not gentle men; be civil in mind and formidable when needed.
I’m tired of constant throat‑clearing disclaimers just to make a point.
We joked about a ritual preface and then moved on, because the work matters more than the preamble.
I’m soon sitting down with Gloria Steinem to talk modern masculinity; my north star for marriage is simple—help each other become your truest selves—and schools teach fractions, not this, even though in love you never really win by beating your partner.
The gentler men’s lane values emotions, striving, and relational skill; the right partner is someone you’ll love talking to for a lifetime, who helps you become.
Becoming yourself is the real grind; mix of traits is healthy, rigid identity is suspect, and my job is storytelling under fire—guiding every emotion in the room toward a just outcome.
What makes for great storytelling?
Deep empathy and full arcs—strengths and flaws; I preempt the ugly texts on direct, own the humanity, and make cross work hard for the other side, which is tougher on video than in person.
How do you know when to leave a relationship?
If you’ve truly tried and still feel alone most of the time, it’s a loud signal; but many spirals are reversible—sexual ruts come from playing the hits, so re‑introduce novelty with a playful dream confession and send warm, unprompted notes that shift momentum.
A great friendship habit is to text people when they pop into your head with a tiny memory.
Old photos nudge me to reconnect, and these free gestures deepen bonds, which is probably why they’re not splashed across headlines.
Deliberate relating is an acquired taste, but it forges deeper friendships and steadier love.
We should normalize training for love; people assume tools mean trouble, just like they assume not drinking means a problem, but being skilled at love boosts everything else.
What questions help decide if it’s over?
A powerful lens is parenting: your kids absorb your dynamic, so ask whether you’d want your child to date someone like your partner—and what advice you’d give a friend in your shoes.
Post‑birth breakups often come from mothers no longer tolerating risk to the child.
You can choose pain for yourself, but it’s different when your choices cause a child to suffer.
Don’t rush to fix; sit with them and offer simple empathy like, that must be hard, how did it make you feel.
My work is asking people in crisis to make big choices, so I’ve learned to deliver hard truths, sit with pain without inflating or dismissing it, and have uncomfortable conversations that protect the relationship.
That’s real alchemy, turning mess into growth, so tell me the worst and best ways to move on after a breakup.
The worst is sprinting into a new romance or a rebound without honesty, because you’re grieving and you can’t skip the stages that lead to acceptance; real recovery starts when the divorce is actually final. The best is a physical or spiritual practice that reconnects you with yourself, not a new partner.
I went back to martial arts after my split, and it gave me focus and a place to put the energy.
Brazilian jiu-jitsu builds trust, community, and safe physical intensity, which is healing when life feels uprooted; it’s you and a room full of people who keep their promises when you tap. More broadly, sweat, routine, and becoming a beginner again steady you, especially when the house goes quiet after the kids leave.
I coped by resetting my sons’ rooms after each handoff to remind myself they’re coming back, then giving myself permission to build my own life in the in‑between; my mom’s rule holds up—have somewhere to go, something to do, and something to love.
I’ve felt that slow slide and then the sudden drop, like a roller coaster tipping over the edge.
The fall can feel like flight until the landing, but there’s wisdom in the wreckage, and therapy helps you find it. Switching therapists showed me how catastrophes shrink over time into a few calm sentences.
People chase aliveness, and movement calms anxiety, which is why a viral photo of Pierce Brosnan and his wife hit me as a pro‑marriage message, not the opposite.
In an industry full of messy splits, a long, happy marriage that raised kids is a win, and aging is part of the deal; we barely notice gradual changes in the person we love. I think of my old dog—his value to me only grew with time—so why wouldn’t two people look at their younger selves and say, we made it, and choose each other again even with other options around.
Beautifully put, man—your framing is generous and clear.
We need a gentle manosphere that defines healthy masculinity without turning it into femininity, because the current setup isn’t working and rising divorces prove it, so let’s fix the parts and get back to real dialogue.
Until next time—appreciate you.
You can find my book How to Stay in Love wherever books or audiobooks live, I’m at nycdivorcelawyer on Instagram, and more of my work is at sextonshow dot com.
Quick final note before we go—if you want a curated list of one hundred books that actually land, I’ve put it together free on my site.