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Divorce Lawyer: “Give her a prenup on the 3rd date” - James Sexton

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… -- 0:00 Are Finance Bros the Worst Divorce Clients? 8:45 The Most Misunderstood Aspects of Prenups 16:46 Does Everyone Actually Need a Prenup? 25:43 Why Avoiding Open Conversations is Costing You 38:39 What Does Good Disagreement Look Like? 47:51 How to Set a Relationship Up for Success 53:55 Will Men Do Anything to Obtain Sex? 01:00:00 How to Help Your Partner Level Up 01:17:46 The Biggest Sign It’s Time to Walk Away 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 - 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 - Get access to every episode 10 hours before YouTube by subscribing for free on Spotify - https://spoti.fi/2LSimPn or Apple Podcasts - https://apple.co/2MNqIgw Get my free Reading List of 100 life-changing books here - https://chriswillx.com/books/ Try my productivity energy drink Neutonic here - https://neutonic.com/modernwisdom - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: https://chriswillx.com/contact/

Chris WilliamsonhostJames Sextonguest
Feb 14, 20261h 58mWatch on YouTube ↗

CHAPTERS

  1. Valentine’s Day confidence, proposals, and why divorce lawyers love the holiday

    James Sexton and Chris Williamson open with a Valentine’s Day framing: romance spikes, confidence rises, and so do future divorce cases. They use it as a springboard to talk about how optimism and big commitments can mask legal and relational realities.

  2. Pro athletes and divorce: money timing, identity loss, and retirement shock

    Sexton explains why professional athletes—especially NFL players—face uniquely high divorce risk. Fast wealth accumulation during marriage, short careers, injuries, and the identity collapse after retirement create conditions that strain relationships.

  3. The hardest divorce personalities: finance ‘risk-takers’ and why they go to war

    Chris asks who is toughest to negotiate against; Sexton points to hedge fund and high-aggression finance types. Their low risk aversion makes them more willing to litigate, prolong conflict, and treat divorce like a high-stakes bet.

  4. Prenups demystified: the government already wrote yours

    Sexton reframes prenups as unavoidable: everyone has one, either drafted by the state or by the couple. Marriage is portrayed as the most legally significant act besides death, yet people enter it with little education about consequences.

  5. Why you can’t measure prenups vs divorce—and why Sexton thinks they reduce breakups

    They discuss why prenup data is hard to track: agreements aren’t publicly filed and celebrity narratives are often false. Sexton shares an experience-based theory that couples who can negotiate prenups tend to build skills that prevent divorce.

  6. ‘Third date prenup’: when and how to raise it without blowing up the romance

    Sexton argues the conversation should happen early—before engagement pressures and sunk costs. He suggests testing attitudes indirectly first, then framing prenups as mutual safety, especially in relationships with financial asymmetry.

  7. Marriage as an economy: roles, equity, baselines, and the myth that commitment ‘fixes’ people

    The conversation broadens into relationship design: marriage involves exchanges of value and changing roles over time. Sexton warns against two opposite mistakes—believing marriage will change someone, and believing marriage will freeze them in place.

  8. Conflict skills that predict longevity: avoid weaponized intimacy and plan your fights

    They explore how successful couples handle lows: arguing about substance, not surface issues, and protecting vulnerability. Sexton’s key rule is never weaponize what your partner confided, and to pre-negotiate how you’ll fight before conflict hits.

  9. De-escalation tactics: ‘deal with it fast’ vs ‘Hit Send Now’ (the email method)

    Chris cites attachment research suggesting rapid repair prevents threats from becoming long-term memory. Sexton agrees on the principle but questions speed in the moment, proposing a written ‘Hit Send Now’ email to reduce defensiveness and improve clarity.

  10. Courtship, standards, and sexual leverage: what men will do to obtain sex

    They discuss modern dating incentives, courtship decline, and how standards shape behavior. Using Roy Baumeister’s work, they argue women’s mate choices can raise or lower the ‘requirements’ men adapt to, and that many men hunger for a clear code and mission.

  11. Helping your partner ‘become more themselves’: emotional integration and the ‘gentlemanosphere’

    The episode shifts to relational growth: partners should help each other become more authentic, not more compliant. They discuss a cultural need for non-toxic masculinity that isn’t simply ‘be more feminine,’ plus the social penalty for discussing gender honestly without constant disclaimers.

  12. When it’s time to walk away: loneliness-with-someone, relief fantasies, and integrity checks

    Sexton offers signs a relationship may be over: persistent emptiness, chronic loneliness, and ongoing desire to escape. Chris adds diagnostic questions, and Sexton emphasizes a powerful lens—what you’d want for your child or best friend in the same situation.

  13. Children amplify decisions: leaving for the kid, not for yourself—and the ‘fixing’ trap

    They explore how parenthood changes tolerance for dysfunction: people may endure mistreatment personally but won’t risk it for a child. They also discuss the misguided urge to ‘fix’ others’ pain and how validation and presence often work better than solutions.

  14. Recovering from breakups: grief stages, body practice, community, and rebuilding routines

    Sexton warns against immediately replacing the relationship and skipping grief. He recommends physical practice and community (e.g., martial arts), reconnecting to neglected parts of self, and building stabilizing routines—especially when co-parenting creates alternating silence and intensity.

  15. Real love vs appearances: the Pierce Brosnan photo, aging, and the ‘bonus rounds’ mindset

    They respond to a viral image mocking long-term marriage by reframing it as evidence of success and devotion. Sexton compares enduring love to caring for an aging dog: attachment deepens with time, shared history, and awareness of finite ‘bonus rounds.’

  16. Wrap-up: where to find James Sexton and his work

    Sexton and Williamson close by reiterating the importance of improving relationship skills and normalizing these conversations. Sexton shares where to get his book and follow his content.

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