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

Episode of Modern Wisdom · September 28, 2026 · 3 h 2 min

Chris Williamson, divorce lawyer James Sexton and comedians Matt McCusker and Rick Glassman riff on marriage, prenups, sex, dating standards, politics in relationships, sitcoms and masturbation.

Summary

In the fourth installment of the Mostly Wise roundtable, Chris Williamson hosted divorce attorney James Sexton and comedians Matt McCusker and Rick Glassman. Sexton opened with a viral story about a client who traced the end of her marriage to her husband no longer buying her granola, mirrored by her own decline in initiating oral sex, and used it to argue that relationships fail when partners stop paying attention. He described tailoring courtroom style to individual judges, said female judges are often harsher on women litigants, and explained why he does not feel guilty about his work, citing faith in the adversarial legal system.

Glassman discussed why he cannot sustain casual sex without a sense of connection, recounting a therapist's suggestion that he experiment with it, and argued that being both attractive and funny is rare because good-looking people have less need to develop social skills. The group reviewed a viral list of dating non-negotiables, and Sexton described prenup trends, including the most extreme enforceable clause he had seen, which reduced alimony for weight gain. Sexton argued couples should openly name changes such as weight gain or declining sex, and said politics, especially after 2016, has driven divorces; McCusker said he largely ignores politics and described learning in marriage counseling to stop keeping score.

Later segments covered Donald Trump's absence from Donald Trump Jr.'s wedding, the decline of multi-camera sitcoms and fragmented audiences, Britain's most-watched broadcasts, "inverse icks," Brazilian jiu-jitsu, post-sex etiquette, Sexton's vasectomy prompted by his ex-wife's prothrombin mutation, and a Playboy survey of Gen Z sexual behavior, whose masturbation figures Glassman doubted. Glassman likened pornography to processed food that requires moderation.

Chapters

  1. 0:32

    Blowjobs and granola

    Sexton recounts a divorce client who realized her marriage was over when her husband stopped replacing her granola, and the group debates asking versus being noticed.

  2. 8:14

    Life as a divorce trial lawyer

    The group discusses client crushes, prenup talks on early dates, Fred Rogers, and how Sexton tailors his style to judges.

  3. 26:28

    Guilt, the legal system and cross-examination

    Sexton explains why he feels no guilt about winning and how lawyers must earn the right to attack a witness.

  4. 30:05

    Rick on casual sex and connection

    Glassman describes experimenting with casual sex on a therapist's advice and why he needs connection to be intimate.

  5. 42:32

    Funny, attractive, and comics' insecurity

    The panel discusses why funny attractive people are rare, comedians dating comedians, reading comments, and McCusker's comedic style.

  6. 54:25

    Dating non-negotiables and wealthy women

    Williamson reads a viral list of dating requirements and Sexton describes what wealthy women want and how men and women marry economically.

  7. 1:02:11

    Prenup clauses and history

    Sexton shares the craziest enforceable prenup clause, women's prenup demands, and the history and popularity of prenups.

  8. 1:13:40

    Weight gain, politics and relationships

    The group debates telling a partner about weight gain, political divides ending marriages, a listener question, and Trump's appeal.

  9. 1:28:20

    Don Jr.'s wedding and keeping score

    Williamson describes Donald Trump Jr.'s lavish wedding, then McCusker and Sexton discuss resentment, anger, sadness and hormones in marriage.

  10. 1:42:09

    Sex, subtext and sitcoms

    Talk moves through women as sexual gatekeepers, framing requests, calling out subtext, improv on set and the decline of multi-cam sitcoms and mass audiences.

  11. 2:06:22

    Inverse icks, basketball and jiu-jitsu

    The group lists satisfying small victories, Glassman discusses natural talents, and Sexton describes the intimacy and trust of Brazilian jiu-jitsu.

  12. 2:31:41

    Post-sex etiquette, vasectomies and masturbation

    Discussion covers aftercare, Sexton's vasectomy, masturbation habits, pornography and a Playboy survey of Gen Z sex lives.

Key points

What was said, by whom, with the exact words. Timestamps jump to the moment.

  • James Sexton

    Sexton says he raises prenups by the third date because couples should discuss the economy of the relationship early.

    “I talk about a prenup on the third date. Like, I think right away that you need to start getting that discourse out there”

    Listen from 9:18 · Prenuptial agreement

  • James Sexton

    Sexton argues that men wrongly assume female judges will favor women, saying women are often merciless toward women.

    “A lot of men think, oh shit, we've got a female judge. And they're completely wrong. Because women are merciless to women a lot of the time”

    Listen from 21:51 · Courtroom advocacy

  • Chris Williamson

    Williamson claims female judges give women harsher and longer sentences on average.

    “dish out harsher sentences, longer sentences, to women on average”

    Listen from 24:24 · Courtroom advocacy

  • James Sexton

    Sexton says facts tend to win in court, so a mediocre lawyer with real facts will beat him.

    “Like a mediocre at best lawyer armed with real facts is going to kick my ass because the facts just have a way of coming out sometimes”

    Listen from 27:34 · Courtroom advocacy

  • James Sexton

    Sexton says he tells young lawyers they must earn the right to aggressively cross-examine a witness.

    “you have to earn the right to beat up a witness. I tell young lawyers who work for me that all the time”

    Listen from 29:29 · Courtroom advocacy

  • Rick Glassman

    Glassman says that without a felt connection he is physically unable to sustain sexual arousal.

    “But if I don't feel a connection with the person, I'm literally not able to maintain an erection”

    Listen from 30:29 · Casual sex

  • Rick Glassman

    Glassman theorizes that people who were attractive when young had less need to develop social skills, making funny attractive partners rare.

    “the better looking somebody is in their developmental years, the less need, not that it's impossible, but the less need it is for them to learn how to connect”

    Listen from 42:51 · Dating standards

  • Matt McCusker

    McCusker argues comedians dating each other would be difficult because comedians tend to be jealous of one another.

    “Because comedians are inherently jealous of each other usually. And then if you're in a relationship”

    Listen from 44:34 · Dating standards

  • James Sexton

    Sexton says the craziest enforceable prenup clause he has seen reduced a wife's alimony by $50,000 for every 10 pounds gained.

    “The craziest thing that was enforceable was if for every 10 pounds that she gained during the marriage, she lost $50,000 in alimony”

    Listen from 1:02:14 · Prenuptial agreement

  • James Sexton

    Sexton says prenups have been meaningfully enforceable since the 1960s but became popular with the general public only about 20 years ago.

    “They've been enforceable in a real way since the 1960s. They really didn't get super popular with the general population until maybe like 20 years ago”

    Listen from 1:10:57 · Prenuptial agreement

  • James Sexton

    Sexton argues couples should openly name changes in their relationship, distinguishing designed relationships from ones on default.

    “I think it's the difference between a relationship that's designed and a relationship that's on default”

    Listen from 1:15:02 · Marriage and long-term partnership

  • James Sexton

    Sexton says his firm saw a wave of divorces in 2017 and 2018 driven by one spouse moving sharply right politically.

    “we got a lot of people in like 2017, 2018 getting divorced because it was like somebody went very far right”

    Listen from 1:17:28 · Political polarization in the United States

  • Matt McCusker

    McCusker says he has ignored politics all his life and has not been affected by doing so.

    “Like I don't, politics, I don't really care at all. And it hasn't affected me”

    Listen from 1:18:45 · Political polarization in the United States

  • James Sexton

    Sexton argues that many right-leaning voters are drawn to Trump's bluntness rather than a cult of personality.

    “They like that this is a person who just says what they're thinking. instead of being full of shit”

    Listen from 1:23:45 · Political polarization in the United States

  • James Sexton

    Sexton recounts a therapist advising him never to yell at a teenager because it signals loss of control.

    “whatever's coming out of your mouth, if you're yelling, what you're telling a teenager is I'm out of control”

    Listen from 1:36:48 · Marriage and long-term partnership

  • James Sexton

    Sexton argues that women have always been the gatekeepers of sex, using leg shaving as an example.

    “have always been the gatekeepers of sex, like 100% of the time. And the example I've always given to this is that women don't like shaving their legs”

    Listen from 1:42:28 · Marriage and long-term partnership

  • Rick Glassman

    Glassman explains that in multi-camera filming, repeated takes get smaller laughs from the live audience because they have already heard the joke.

    “The second take you do it again, it doesn't get as big of a laugh because they heard it already”

    Listen from 1:52:36 · Multi-camera sitcom

  • James Sexton

    Sexton suggests a new Friends-style multi-cam show could feel fresh to young viewers who did not grow up with the format.

    “for young people who didn't grow up on that, they might be like, oh, this is something different”

    Listen from 1:57:49 · Multi-camera sitcom

  • James Sexton

    Sexton describes Brazilian jiu-jitsu as a form of physical intimacy and trust between men.

    “it's physical intimacy between two men and a tremendous amount of trust in each other physically”

    Listen from 2:22:01 · Brazilian jiu-jitsu

  • James Sexton

    Sexton says his vasectomy did not change any aspect of his sexual experience.

    “It just cuts off the production. It doesn't change anything about any aspect of your sexual experience”

    Listen from 2:39:46 · Vasectomy

  • Linked moment · 2:53:45Skip to 2:53:45 using a listen link in the info box.

    Rick Glassman

    Glassman compares pornography to processed food, saying it serves a purpose but is dangerous and requires moderation.

    “I think that pornography, much like processed foods in the cabinet, serve a purpose and I understand its want. I think it's dangerous”

    Listen from 2:53:45 · Pornography

  • Chris Williamson

    Williamson cites Playboy's 2026 survey finding that one in five Gen Z respondents are virgins and most recent sex occurs with a single partner.

    “One in five Gen Zers are virgins. 45% of those who had sex in the last three months had just one partner”

    Listen from 2:54:33 · Playboy 2026 Gen Z sex survey

  • Rick Glassman

    Glassman doubts the survey's masturbation figures, arguing young respondents lie about it.

    “I think young kids won't admit that they jerk off and they're lying to the testers”

    Listen from 2:54:54 · Playboy 2026 Gen Z sex survey

  • Matt McCusker

    McCusker says that as he ages he wants to avoid porn, and skipping porn makes skipping masturbation easier.

    “If I'm not going to watch porn, if I, you know, I can, if I can skip porn, I can probably skip”

    Listen from 2:56:55 · Masturbation

People

In the conversation

Discussed

  • Fred RogersAmerican children's television host of Mister Rogers' Neighborhood
  • Donald Trump Jr.Son of Donald Trump, reportedly discussed as Apprentice host
  • Donald TrumpPresident of the United States whose conduct of the Iran war is the episode's main subject
  • Lindsay ClancyMassachusetts mother whose criminal case divided public opinion
  • Brooke LeBlancTech executive whose viral list of dating requirements was discussed
  • Lily PhillipsBritish adult content creator and guest on Glassman's podcast
  • Bonnie BlueAdult content creator mentioned as Lily Phillips' competitor
  • Shane GillisAmerican comedian and co-creator of the Netflix series Tires
  • Mikey MusumeciBrazilian jiu-jitsu competitor

Topics

More from Modern Wisdom

From the publisher

In the fourth episode of Mostly Wise, we explore: If there is any sexual tension between clients and divorce lawyers. Why Rick can't hook up with someone he isn't in love with. Where all the hot goth girls up and disappeared to. The craziest clauses found in James' clients' prenuptial agreements. How to talk to your partner about gaining weight. Gen Z's big problem with being the most sexless generation. And much more... Guests James Sexton is a New York-based divorce attorney and author, known for his expertise in family law and insights on marriage and divorce. Matt McCusker is a comedian, writer, author and podcaster. Rick Glassman is a comedian, actor, and podcaster. Sponsors: See discounts for all the products I use and recommend: ⁠https://chriswillx.com/deals⁠ Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom Get up to $350 off the Eight Sleep Pod 6 at https://eightsleep.com/modernwisdom Get 160+ lab tests for just $365 and save an extra $25 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 Get ChatGPT to explore ideas, solve problems, and learn faster at ⁠https://chatgpt.com Timestamps: (00:00) The Problem With Blowjobs and Granola (08:16) Why Being a Divorce Lawyer Is Surprisingly Sexy (13:39) Who Is Fred Rogers? (17:07) Do People Hide Their Friendship With James? (20:29) Why James Tailors Every Case to the Judge (26:28) Does James Ever Feel Guilty About Winning? (30:06) Does Rick Need to Have More Casual Sex? (42:13) Why Funny and Attractive Is So Hard to Find (54:31) Are Modern Dating Standards Getting Ridiculous? (58:50) The Craziest Prenup Clause James Has Ever Seen (01:04:31) What Are Women Demanding in Prenups? (01:13:42) Can You Tell Your Partner They’ve Gained Weight? (01:17:06) Are Personal Politics Ruining Relationships? (01:28:19) Did Donald Trump Really Miss His Son’s We…

Summary, chapters and key points were generated from the episode transcript on October 3, 2026. Quotes are checked word for word against the transcript.

Categories: Relationships·Sexuality·Comedy Interviews