James Sexton, Rick Glassman, Matt McCusker - Mostly Wise #4 - #1156

What It Covers

Divorce attorney James Sexton joins comedians Rick Glassman and Matt McCusker for a wide-ranging roundtable covering relationship deterioration signals, prenuptial agreements, courtroom psychology, sexual compatibility, political disagreements in partnerships, and the unspoken economic dynamics that shape modern marriages and divorces, drawing on Sexton's 27 years of New York family law trial experience.

Key Questions Answered

• •Relationship Deterioration Signals: Small, unsolicited acts of care function as the most reliable early indicators of a relationship's health. Sexton describes a client who recognized her marriage was failing when her husband stopped automatically restocking her granola — something he had done without being asked. When partners stop performing these spontaneous, unrequested gestures, it signals a fundamental shift in attentiveness and emotional investment before larger problems become visible.
• •Prenuptial Agreement Framing: Sexton argues prenups should be introduced by the third date, framed not as legal protection but as a mutual conversation about what each partner needs to feel safe. The productive question is not "how do we divide assets" but "what would you need if this ended?" This reframe transforms a transactional document into an early compatibility test that surfaces expectations around economics, sacrifice, and long-term commitment before emotional investment deepens.
• •Courtroom Persuasion Strategy: Sexton's principle — good lawyers know the law, great lawyers know the judge — translates into concrete behavioral adaptation. He researches each judge's interests and adjusts argument language accordingly, using sports metaphors for sports fans and deferential language for formality-preferring judges. He also deliberately cultivates goodwill with court reporters and officers, reasoning that their informal post-session commentary to the judge can influence perception outside formal proceedings.
• •Wasteful Dissipation of Marital Assets: In divorce proceedings, one spouse secretly spending shared marital funds — such as $150,000–$200,000 in a single Las Vegas night — constitutes a legally actionable claim called wasteful dissipation of marital assets. The injured spouse can pursue recovery of up to half those funds. This legal mechanism applies to any unilateral, non-consensual spending of joint money on personal indulgences, including luxury goods like Birkin bags purchased without the other partner's knowledge.
• •Sexual Compatibility and Intentionality: Glassman describes discovering through therapy-assigned casual sex experiments that his arousal functions as a reliable signal of genuine connection rather than physical attraction alone. When he felt obligated rather than genuinely interested, he experienced performance issues. His practical solution is explicit pre-encounter communication — stating directly that sex is possible but not assumed — which he reports functions as an effective filter, eliminating partners incompatible with his relational needs before physical encounters create awkward obligations.
• •Political Disagreement in Relationships: Sexton observes a measurable spike in divorce consultations following the 2016 election, driven by ideological incompatibility between right-leaning men and left-leaning women. His parents — a Reagan conservative Naval Academy graduate and a near-Marxist — maintained a 50-plus-year marriage by separating political disagreement from shared family values. The actionable takeaway: couples should distinguish between surface-level political positions and the underlying values driving those positions, which are often more compatible than the positions themselves suggest.
• •Relationship Design vs. Default: Sexton identifies the core failure pattern across his divorce cases as couples operating on relational default rather than intentional design. When behaviors change — frequency of sex decreases, weight changes, emotional distance grows — most couples avoid naming it directly. His prescription is to verbally acknowledge changes as they occur, without assigning blame, and jointly determine whether the change is acceptable or requires adjustment, treating the relationship as an ongoing negotiation rather than a static agreement made at the altar.