Modern Wisdom

#1059 - James Sexton - Divorce Lawyer: “Give her a prenup on the 3rd date”

February 14, 2026

Key Takeaways Copied to clipboard!

  • Every married person already has a prenup, which is either the one written by the government (statutory law) or one written by the couple themselves. 
  • The process of negotiating a prenup often reveals the couple's ability to have brave, vulnerable conversations, which bodes well for the relationship, and conversely, some couples break up during the prenup negotiation itself. 
  • Handling bad times, not just enjoying the highs, is the true predictor of a marriage's success, making early, substantive conversations about conflict resolution crucial. 
  • Divorce lawyers possess unfiltered data on relationships because clients do not lie to them, unlike therapists or survey respondents. 
  • Men will often adapt their behavior to meet the standards women set for obtaining sex, suggesting women are the historical gatekeepers of sexual access. 
  • The goal of a great marriage should be for both partners to help each other become the most authentic version of themselves while remaining each other's favorite person. 
  • Divorce is fundamentally a deep disconnection, often occurring slowly over time, mirroring the way people go bankrupt: very slowly and then all at once. 
  • Experiencing the full spectrum of human emotion, including pain like heartbreak, is vital for feeling truly alive, contrasting sharply with emotional numbness. 
  • Long-term successful relationships, like the one exemplified by Piers Brosnan and his wife, demonstrate a beautiful expression of love where partners continue to see the best in each other despite aging. 

Segments

Valentine’s Day and Divorce
Copied to clipboard!
(00:00:00)
  • Key Takeaway: Valentine’s Day generates a significant influx of future divorce clients due to increased proposals and subsequent poor choices.
  • Summary: The speaker notes that Valentine’s Day is the best holiday for his profession because it leads to a large number of future divorce filings. High confidence levels on this day often result in proposals, statistically increasing the likelihood of future legal separation. The host offers a free resource of 50 viral questions to connect deeply or 25 questions to determine if a relationship should end.
Athlete Marriages and Discipline
Copied to clipboard!
(00:00:59)
  • Key Takeaway: Professional athletes’ monastic discipline focused on a single task can be a useful skill in marriage, but short careers often lead to post-retirement marital instability.
  • Summary: Athletes’ ability to focus intensely on one task can translate well into marriage, preventing distraction. However, NFL players often marry early, acquire massive wealth during the marriage without a prenup, and face high divorce rates (near 70%) upon retirement due to feeling unmoored by the sudden silence after a structured career.
Difficult Divorce Professions
Copied to clipboard!
(00:06:28)
  • Key Takeaway: Hedge fund managers and traders are the most difficult professionals to negotiate with during divorce due to their high risk tolerance and aggression.
  • Summary: In New York City, finance professionals, particularly hedge fund guys, are nightmare adversaries in divorce litigation because they lack risk aversion and prefer to roll the dice by going to trial. Conversely, quantitative analysts (quant guys) are easier to deal with as they rely on math and risk versus reward calculations to determine settlement offers.
Understanding Prenuptial Agreements
Copied to clipboard!
(00:08:46)
  • Key Takeaway: A prenup is simply a contract defining the rule set for asset division if a marriage ends in divorce, which is inevitable alongside death.
  • Summary: Everyone has a prenup; it is either the one dictated by state law or a contract written by the couple. Marriage is the most legally significant act a person undertakes, affecting property rights and support obligations, yet couples receive no guidance on these state-imposed rules. Discussing a prenup early establishes safety and clarifies the rule set before conflict arises.
Prenups and Divorce Likelihood
Copied to clipboard!
(00:16:46)
  • Key Takeaway: The speaker theorizes that people who get prenups are statistically less likely to divorce because the necessary open conversation builds relationship strength.
  • Summary: It is impossible to track prenup correlation with divorce because contracts are not publicly filed, and clients rarely return to the same lawyer for divorce if they had the prenup done elsewhere. The act of having the brave, vulnerable conversation required to negotiate a prenup, while optimism is high, seems to foster a skill set that promotes long-term relationship success.
Broaching the Prenup Conversation
Copied to clipboard!
(00:19:44)
  • Key Takeaway: The prenup discussion should be introduced early, perhaps by the third date, by framing it as a conversation about mutual safety and aligning on major life questions.
  • Summary: The speaker suggests broaching the topic by gauging the partner’s general feelings about prenups while discussing other major life questions like children and geography. A prenup is fundamentally about ensuring both partners feel safe, especially in relationships with significant wealth disparity, by defining how assets will be divided if trust is broken.
Setting Relationship Success
Copied to clipboard!
(00:38:39)
  • Key Takeaway: Good disagreement is substantive, focusing on the merit of the issue rather than using personal vulnerabilities as leverage.
  • Summary: Couples must never weaponize intimacy—the knowledge of a partner’s soft targets—as this causes irreparable harm to the connection. It is wise to pre-agree on how to argue, such as establishing a code word for a break or determining if immediate resolution or time apart is preferred when conflict arises.
Divorce Lawyer’s Unique Data Access
Copied to clipboard!
(00:55:24)
  • Key Takeaway: Divorce lawyers see unfiltered client data, including texts and receipts, because clients cannot lie under attorney-client privilege.
  • Summary: People do not lie to their divorce lawyer because they must reveal everything necessary for legal representation. This access provides a unique, unvarnished view into personal conduct, unlike data gathered by therapists or surveys. The lawyer has seen every side of every issue in thousands of unhappy marriages.
Men’s Hunger for a Code
Copied to clipboard!
(00:56:36)
  • Key Takeaway: There is a current hunger among men for a defined ‘code’ or set of expectations to guide their behavior.
  • Summary: The speaker believes men aspire to figures who operated with a strict code, like literary samurai or protectors. This code provides clarity on what is expected and what is forbidden in their conduct. Women historically acted as gatekeepers of sex, requiring men to demonstrate discipline and seriousness to earn intimacy.
Masculinity and Presentation
Copied to clipboard!
(00:57:47)
  • Key Takeaway: Traditional masculine presentation, like wearing a suit, signals seriousness and commitment, which is appealing to women.
  • Summary: The speaker notes that his professional attire signals he takes the world and his role seriously, attracting positive attention from women. This presentation contrasts with the casualness of hoodies, suggesting formality communicates reliability. The combination of traditional masculinity (like tattoos) and formality (like a suit) appeals as a ‘Clark Kent/Superman’ archetype.
The Gentlemanosphere and Social Land Acknowledgement
Copied to clipboard!
(01:01:36)
  • Key Takeaway: The need to constantly preface points with social disclaimers (’throat clearing’) stifles direct conversation on important topics.
  • Summary: The speaker laments the necessity of adding social land acknowledgments or disclaimers before discussing topics like birth rate decline or gender dynamics. This constant qualification makes discussions feel hackneyed and prevents getting to the core issue. The ‘gentlemanosphere’ aims for civilized discussion while maintaining masculine rigor.
Ideal Marriage Goal and Relationship Skills
Copied to clipboard!
(01:06:40)
  • Key Takeaway: The highest goal of marriage is helping a spouse become their most authentic self while remaining their favorite person.
  • Summary: Marriage should function as a vehicle for mutual transformation, where partners facilitate each other’s authentic development. Relationship skills, like how to argue well or communicate difficult truths, are rarely taught despite their critical importance. Winning an argument with a spouse is a net loss because it diminishes the other person.
Storytelling Through Vulnerability
Copied to clipboard!
(01:14:20)
  • Key Takeaway: Effective storytelling, especially in high-stakes situations like court, requires incorporating the full range of human experience, including failure.
  • Summary: Great storytelling involves dynamic imagination and presenting a narrative that includes both strengths and weaknesses. The ‘Eight Mile approach’ involves proactively revealing known weaknesses to control the narrative and build sympathy. Presenting oneself as a flawed but striving hero makes a character relatable and sympathetic.
Knowing When to Quit Relationships
Copied to clipboard!
(01:17:46)
  • Key Takeaway: A relationship may need ending if one consistently feels empty and alone while with the partner, or if one would feel relieved if the relationship ended suddenly.
  • Summary: The humorous adage that ‘winners never quit’ fails if one never wins and never quits, indicating foolish persistence. A unique hell is feeling profoundly lonely while physically present with a partner. Recovery from divorce only truly begins once the legal process is officially finalized, marking the end of the relationship’s death.
Reversing Sexual Monotony
Copied to clipboard!
(01:19:25)
  • Key Takeaway: Sexual monotony in monogamy results from playing ’the hits’ repeatedly without introducing novelty or open communication.
  • Summary: Couples often fall into routine by sticking to what they initially discovered both partners liked, creating a predictable pattern. Deviating from this routine can cause unspoken suspicion if communication is lacking. Introducing novelty can be achieved non-confrontationally, such as by describing a fantasy dream to initiate dialogue.
Free Relationship Advice vs. Commercial Incentives
Copied to clipboard!
(01:24:58)
  • Key Takeaway: Actionable, free advice on improving relationships and friendships is rarely promoted because there is no commercial incentive for it.
  • Summary: Simple, free actions like texting friends when you think of them create deep connection but lack commercial viability. Similarly, learning to be good at love is a teachable skill that should be valued, as poor relationships derail even successful careers. The value of a good partner is an incredible asset in all areas of life.
The Impact of Children on Relationship Endings
Copied to clipboard!
(01:33:44)
  • Key Takeaway: Women often leave relationships after a child is born because they cannot tolerate seeing their child potentially mistreated by an incompetent partner.
  • Summary: While a woman might endure personal mistreatment, the potential suffering of her child becomes an insurmountable factor. Watching a parent’s dynamic sets a template for future partners, meaning a daughter learns what treatment is ’normal’ from her parents’ relationship. The urge to fix another’s pain is often a false face for the urge to rule.
Importance of Social Connection
Copied to clipboard!
(01:47:09)
  • Key Takeaway: Divorce is the ultimate manifestation of deep disconnection, underscoring the human need for connection through pets or friends if a primary relationship fails.
  • Summary: Humans are social creatures who require connection; divorce represents a profound failure in this area. Falling out of love often happens gradually, similar to how one goes bankrupt, leading to a sudden, painful realization. This process can feel like falling off a roller coaster, initially feeling like flying before hitting the ground.
Value of Life’s Painful Experiences
Copied to clipboard!
(01:48:13)
  • Key Takeaway: Major life pains, including loss and relationship endings, are highly formative experiences that provide significant emotional material and learning.
  • Summary: Looking back on life’s great pains, such as losing a parent, reveals the immense emotional material contained within those events. The journey through hardship leads to substantial personal learning and shapes one’s identity. Truly romantic stories often involve riding the full spectrum of connection and subsequent disconnection.
Therapy and Self-Reflection
Copied to clipboard!
(01:49:10)
  • Key Takeaway: Therapy serves two primary functions: crisis management during life fires and proactive self-improvement by identifying personal blind spots.
  • Summary: Therapy is sought both when life is on fire (e.g., divorce, death) and for ongoing self-improvement to see blind spots and improve one’s being. Switching therapists after 15 years forces one to summarize life events, revealing how intense past ’epic tales’ shrink into brief summaries upon gaining perspective. The intensity of past crises often diminishes when viewed with distance.
Feeling Alive Through Intensity
Copied to clipboard!
(01:50:48)
  • Key Takeaway: People seek to feel alive, and intense emotional states, whether joyful or painful like heartbreak, provide this necessary aliveness, which is preferable to numbness.
  • Summary: The feeling of being alive is sought through intense experiences like closing a deal, selling a business, or experiencing love and heartbreak. Painful experiences are better than the ‘dead mode’ of a forgettable Wednesday afternoon. One should aim to earn all their scars rather than dying without having experienced significant life events.
Action as Anxiety Antidote
Copied to clipboard!
(01:51:44)
  • Key Takeaway: Establishing a routine and taking action is the direct antidote to anxiety because anxiety struggles to target a moving object.
  • Summary: After a major event, rediscovering lost routines and maintaining activity helps manage anxiety. Anxiety is effectively countered by action, as it ‘hates a moving target.’ This principle applies to recovering from emotional turmoil.
Marriage Success vs. Aging Critique
Copied to clipboard!
(01:52:05)
  • Key Takeaway: Critiques of long-term partners aging inappropriately reveal the critic’s shallowness, as aging appropriately alongside a partner is a sign of a flourishing, successful marriage.
  • Summary: The viral image critique of Piers Brosnan’s wife aging was best countered by framing it as an advertisement for marriage, showing how well he flourished alongside her. In long-term relationships, partners often don’t notice gradual changes in each other, similar to how a mother still sees her child as young. Choosing to stay with a partner through aging is a beautiful expression of enduring love.
The Value of Long-Term Commitment
Copied to clipboard!
(01:54:45)
  • Key Takeaway: Love deepens as a partner ages and faces challenges, exemplified by the speaker’s increased love for his aging, deaf dog.
  • Summary: The speaker loves his 16-year-old dog more as it ages and loses faculties, contrasting sharply with the desire to replace an old dog with a puppy. Long-term partners who have navigated difficulties together can look back and appreciate their journey, recognizing they have achieved ’escape velocity’ together. Admiration for a long, happy marriage should supersede shallow critiques based on physical appearance.
Need for Dialogue and Masculinity
Copied to clipboard!
(01:56:49)
  • Key Takeaway: There is a critical need for a serious, meaningful dialogue, particularly concerning non-toxic masculinity, as the current state of relationships is failing many people.
  • Summary: The speaker advocates for a necessary dialogue within the ‘gentlemanosphere’ to address what constitutes non-toxic masculinity, noting that femininity is not the answer. The high divorce rate, despite no one intending to divorce, proves the current system is not working for individuals. Fixing the individual components of relationships is necessary before meaningful dialogue can resume.
Guest Contact Information
Copied to clipboard!
(01:58:00)
  • Key Takeaway: James Sexton’s book, ‘How to Stay in Love,’ is available everywhere, and he can be found on Instagram and his website.
  • Summary: James Sexton’s book, ‘How to Stay in Love,’ can be purchased where fine books are sold or listened to on Audible. He posts content on Instagram under the handle NYC Divorce Lawyer. Further information and appearances are available on sextonshow.com.