James Sexton: A New York divorce lawyer with over 25 years of experience working in the high and ultra-high net worth space, and author of the relationship book 'How to Stay in Love.' A former hospice volunteer whose master's thesis studied the semantics of death and dying.
What this episode covers
Sexton and Steven Bartlett explore why marriages fail, framing divorce alongside death as an inevitable ending people refuse to discuss honestly. Sexton introduces 'slippage', the slow accumulation of small neglects that ends relationships, and argues couples lose connection by forgetting to 'water the plant.' He reframes prenups as a healthy, even romantic, conversation and explains how children, infidelity, money, crypto and hidden wealth play out in high-net-worth divorces. He closes with his controversial view that children should not be a person's greatest accomplishment, and that obsessing over kids while neglecting a partner is a fast track to his office.
The guest's own work
How to Stay in Love
James Sexton
“if you didn't go by the book last time, you have to go buy the book. It's called How to Stay in Love.”— Steven Bartlett
Also referenced (named, not recommended)
The Sun Also Rises
Ernest Hemingway
“Ernest Hemingway said in um The Sun Also Rises, um I I went bankrupt the same way anybody does. Very slowly and then all at once.”— James Sexton
Batman Begins
Christopher Nolan
“you know, like in Batman Begins, you know, sort of in his in his flip-flops and robes sort of wanders up the mountain”— James Sexton
Will & Grace
NBC
“I mean, you know, Will and Grace, like Will couldn't even kiss his boyfriend on TV. He couldn't really even have a boyfriend.”— James Sexton
Big reveals from this episode
- Recounts a case he won that he should have lost, representing an abusive pimp against an inexperienced state-appointed lawyer who couldn't get a photo into evidence.
- Declares 'every single marriage ends in death or divorce' and that society refuses to talk about either.
- States he doesn't believe in the legal institution of marriage, calling it largely performative.
- Calls marriage an 'incredibly dangerous idea,' arguing it has a worse failure rate than skydiving.
- Reveals no wedding expo would rent him a table to promote prenups, they refused his money.
- Says many publicly 'wealthy' people, especially celebrities, are leveraged to the hilt and actually broke.
- His most controversial opinion: children should not be the most important thing or greatest accomplishment in your life.
- Claims people obsessed with their children stop paying attention to their partner, leading straight to divorce.
Worth remembering
- Roughly 86% of people remarry within 5 years of their divorce, despite swearing they never will.
- His fastest case was a marriage that lasted just 72 hours before annulment.
- Cites a 56% divorce rate, plus another 20-30% staying together miserable.
- At least 80% of clients who reach his office had infidelity as a factor.
- Jokes divorce lawyers owe Steve Jobs gratitude, shared Apple IDs surface lovers' texts on family iPads weekly.
- In New York, child support is roughly 17% of gross income for one child, scaling to 31% for four.
- His largest child support case was $65,000 a month, covering security, private school and more.
- Notes Jeff Bezos paid likely the largest divorce settlement in history because his ex-wife was there for Amazon's whole trajectory.
- Shares the Zen idea: 'if you don't learn to find joy in the snow, you will have less joy and precisely the same amount of snow.'
- His single piece of relationship advice: pay attention to three things, the you, the me, and the we.