Episodes featuring Rick Glassman

Browse episodes where Rick Glassman appears as host or guest. View all episodes →

Chris Williamson
The Craziest Prenup A Divorce Attorney Has Ever Seen

Divorce attorney James Sexton joins Chris Williamson, Rick Glassman, and Matt McCusker to discuss unusual prenups and how they can be used as a tool for designing relationships, not just planning for divorce.

Chris Williamson
James Sexton, Matt McCusker & Rick Glassman - Mostly Wise #4
Chris Williamson · with James Sexton, Matt McCusker, Rick Glassman · Sep 28, 2026 · 2 recommendations

Divorce attorney James Sexton joins Chris Williamson, Rick Glassman, and Matt McCusker to discuss what makes relationships work or fail, from prenups to courtroom strategy.

Chris Williamson
The Case Against Condoms & Fake Friendship - Rick Glassman (4K)
Chris Williamson · Feb 16, 2026 · 1 recommendation

Comedian Rick Glassman joins Chris Williamson to talk about authenticity in friendships and relationships, and how being upfront about your quirks prevents resentment.

Chris Williamson
A List of Things That Kill Your Aura - Rick Glassman
Chris Williamson · Feb 13, 2026

Chris Williamson and Rick Glassman riff on everyday moments that kill your dignity, then dig into why social conversation rules are so much harder to navigate than formal game rules.

Chris Williamson
The innocence of silly humor - Rick Glassman
Chris Williamson · Feb 10, 2026

Rick Glassman and Chris Williamson discuss silly humor, why finding fart jokes funny signals emotional openness, and how humor can defuse shame in difficult conversations.