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

In this podcast episode, James Sexton, an experienced divorce lawyer based in New York City, dives deep into the complexities of marriage, relationships, divorce, and modern masculinity. The conversation covers a broad range of topics including the dynamics of professional athlete marriages, the misunderstood nature of prenuptial agreements, how couples can argue and connect better, and the evolving challenges men face today. Sexton also shares personal insights and practical advice on navigating love, breakup, and self-growth.

Marriages and Divorces Among Professional Athletes

Sexton discusses the unique pressures professional athletes face in their relationships. Athletes often dedicate their youth to monastic discipline centered on their sport, which can help in marriage due to their focus and avoidance of distractions. However, particularly in leagues like the NFL with short career spans, athletes often accumulate massive wealth early while married to partners from their early days, typically without the legal savvy to secure prenups. This sets the stage for complicated and costly divorces, with rates among professional athletes reaching nearly 70%, significantly higher than the general population. The sudden loss of structure, purpose, and daily routine after retirement is a major strain leading to divorces within the first year post-retirement. Sexton likens their experience to soldiers coming home from war, requiring extensive transition support that unfortunately is lacking for many athletes.

The Difficulty of Negotiating with Different Professions

Sexton identifies finance professionals, especially hedge fund managers, as among the toughest adversaries in divorce negotiations. Their high risk tolerance and aggressive mindset make them willing to go to trial, making them challenging to negotiate with. Contrastively, quantitative analysts are more methodical, providing detailed calculations and risk assessments that are easier to work with. Sexton's courtroom specialization involves "full contact storytelling," where he aggressively advocates for clients in trial situations—akin to wielding a chainsaw rather than a scalpel in contrasts to typical divorce mediations.

Understanding Prenuptial Agreements

One of Sexton's core teachings is that every marriage effectively has a prenuptial agreement, either implicitly through government-imposed laws or explicitly through contracts written by the couple. He stresses the importance of recognizing marriage as a legally binding contract with significant consequences regarding property, support obligations, and inheritance rights—none of which are adequately communicated at the time of marriage. Contrary to popular belief, prenups are not a sign of mistrust or pessimism; Sexton argues that couples who negotiate prenups often engage in open, brave discussions about safety and vulnerability, which predict healthier relationships. His recommendation is to normalize prenups and discuss them early—even suggesting the "third date" as a potential moment to broach the topic gently, gauging partner attitudes through discussions about famous couples or hypotheticals.

Marriage as an Economy and Behavioral Agreements

Sexton reframes marriage as an economy involving exchanges of value, where equity rather than strict equality matters. He advocates for open conversations about how partners contribute differently, whether through childcare, financial support, or emotional labor, emphasizing that relationships should avoid patterns of exploitation or imbalance. Establishing baselines for expectations early in the relationship helps couples notice and address changing dynamics as time passes. He notes that assumptions that marriage will change fundamental traits or behaviors of a partner are flawed, as is the belief that marriage freezes people in time. Openly discussing these realities helps couples manage gradual shifts while preserving connection.

The Legal Quirks of Divorce and Jurisdictional Differences

James highlights peculiarities in divorce law across different states, such as New York's unique evidentiary rules allowing hearsay testimony from child protective workers without the opportunity for cross-examination. He mentions surprising laws that still exist, like some states criminalizing consensual sexual activities often taken for granted elsewhere, exposing the inconsistencies and idiosyncrasies within family and criminal law. This reinforces the complexity and unpredictability individuals face navigating divorce and marital legal matters.

Arguments, Weaponized Intimacy, and Healthy Disagreements

Sexton teaches couples that "lows, not highs" define relationship longevity and success. Healthy arguments are substantive, addressing underlying feelings rather than surface issues like chores or sex frequency. He warns strongly against weaponizing intimacy—using vulnerable knowledge about a partner to inflict emotional pain—which causes irreparable damage. Instead, couples should have meta-conversations about how they argue, establish mutual "code words" or breaks to de-escalate conflicts, and aim to resolve disagreements quickly (ideally within minutes) to avoid long-term emotional harm. Sexton recommends thoughtful communication methods, including writing emails to articulate tough feelings clearly without triggering defensiveness.

The Role of Progressive Revelation and Courtship

The importance of "progressive revelation" in dating—gradually disclosing deeper aspects of oneself rather than rushing intimacy—is emphasized. Sexton laments its loss in hookup culture, where fast exposure to all facets can erode mystery and anticipation. He refers to tools like viral relationship question lists or card games that promote meaningful conversation and discovery between partners, aiding connection building. Drawing on evolutionary science, he also discusses male bonding mechanisms and the value of "good boy points" earned through gestures that nurture connection and signal seriousness.

Modern Masculinity and the Gentleman Sphere

A recurring theme is the need to redefine masculinity in non-toxic terms that integrate emotions and relational skills. Sexton joins voices like Scott Galloway and Richard Reeves advocating a "gentleman sphere" that balances strength, discipline, and emotional openness. He challenges toxic suppression of feelings and highlights men's hunger for codes of conduct centered on integrity and respect. Discussing male sexuality, he underscores women's historical role as gatekeepers of sex and the importance of mutual standards fostering healthy relationships. Sexton critiques contemporary cultural trends that stigmatize masculinity or obscure men's roles, instead promoting a vision where men can pursue authentic growth while valuing deep partnership.

The Power and Complexity of Storytelling in Court and Relationships

Given his experience as a trial lawyer, Sexton reveals how storytelling shapes human perception. Effective narratives balance strengths and weaknesses, making clients relatable by exposing vulnerability alongside heroism. This principle extends to relationships, where honest storytelling about feelings and failures can foster empathy and deepen bonds, though it requires courage. Sexton compares courtroom dynamics to high-stakes performance, where emotional manipulation aims to paint the fullest picture. He warns that many problems emerge from miscommunication or defensive storytelling, recommending mindful dialogue as a remedial tool.

Recognizing When to Leave a Relationship

Deciding whether to stay or leave is one of the hardest choices partners face. Sexton offers reflective questions that help individuals assess their emotional state, such as whether they would feel relief or disappointment if the relationship ended suddenly, or if the predominant feelings are negative enough to sustain long term. Another powerful measure is imagining whether one would want their child to date their partner, highlighting concerns for family welfare. He notes that breakups often follow childbearing due to added pressures, and that witnessing potential harm to children motivates many to exit toxic environments. Sexton also stresses that loneliness while being with someone—feeling disconnected despite proximity—is a unique and painful signal.

Managing Breakups and Moving On

Sexton advises against immediately entering new relationships after a breakup, emphasizing the importance of grieving and processing loss akin to stages of death and dying. He observes that healing commonly begins only after finalizing divorce, highlighting the prolonged emotional toll. To recover healthfully, reconnecting with one's body through physical practices—whether martial arts, yoga, or other sports—is crucial for mental and emotional well-being and fosters community bonds. Sexton shares his personal experience returning to Brazilian jiu-jitsu after divorce, highlighting trust and physical connection in male camaraderie. Routines, caregiving activities, and finding new sources of connection also help rebuild identity post-separation.

Love, Vulnerability, and the Fear of Not Being Worthy

Sexton explores the paradox of vulnerability and intimacy in love, expressing that deep connection requires revealing one's "ugly" or uncomfortable truths and still being accepted. He discusses the challenging internal narrative many face—believing they are unworthy of love due to their flaws and weaknesses. True love, to him, embraces the full human messiness rather than just idealized versions. Sexton sees love as an act of bravery because it entails risk of loss and hurt but promises profound human transformation. This vision contrasts sharply with performative social media personas where authenticity is often sacrificed.

Practical Relationship Advice: Small Gestures and Communication

Throughout, Sexton emphasizes the power of simple gestures: texting partners or friends just to say "I was thinking of you," reminiscing about how couples met to rekindle softness, or playful acts like sending nudes or affectionate messages midday. These low-cost behaviors enhance connection and prevent emotional drift. He also recommends creating meta-communication about how to debate, set boundaries, and navigate challenges collaboratively. Sexton encourages couples to periodically assess and talk about changes, needs, and expectations, thus maintaining transparency and preventing resentments from festering.

Public Perceptions and Cultural Resistance to Relationship Advice

Sexton notes that unlike diet advice or fitness, relationship advice is often stigmatized; people assume those seeking it have problems, rather than it being a proactive self-improvement tool. Similarly, he observes that social discourse around masculinity and romantic standards is fraught and frequently misunderstood, with many fearing frank conversations will be seen as misogynistic. Sexton advocates for culturally normalizing open, honest dialogue about love, sex, and masculinity without defensiveness or polarization. He underscores the value of recognizing emotional needs and relational skills as fundamental parts of a fulfilling life.

The Aging Couple and Enduring Love

The podcast closes with Sexton reflecting on iconic images of long-term couples like Pierce Brosnan and his wife, challenging shallow societal standards focused on youth and attractiveness. Sexton highlights the beauty in aging together, accepting physical changes, and flourishing through shared history and mutual support. He likens this to caring for a beloved aging pet—an act of love emphasizing presence, acceptance, and gratitude for the time granted rather than futile attempts to resist change. This mature love stands as an aspirational model amid a culture often obsessed with novelty and appearance.

Resources and Closing Notes

James Sexton's book How to Stay in Love is available widely, offering an extended exploration of many themes discussed. Listeners are invited to follow him via Instagram and his website for more insights. The conversation underscores the importance of fostering a "gentleman sphere" of thoughtful modern masculinity, cherishing relational depth, and approaching love as a lifelong skill requiring practice, honesty, and courage.