Judson counsels Brian on his continuing saga of the hookup that just won’t happen. The two are then joined by Dr. Israel Martinez, author of the new book, “Enhancing Pleasure for Gay Men: A Clinical Guide for Healing and Acceptance Through Better Sex.” Israel talks to Judson and Brian about shame and validation, the concept of Responsive Arousal, his own Daddy issue around the pressure to have kids, and what self care looks like for him. Israel also joins the two in helping a listener process how his lack of a father figure growing up impacted his masculinity.

Judson analyzes his recent ambivalence about sex and reveals he’s having a “Bottom Autumn.” Brian shares his daughter’s follow-up questions on the sex talk and comes clean about why he may have sounded so jealous on the recent Jealousy episode. The two then compare how they each answer the age-old question asked on the apps, “Into?,” and dive into an exploration of kinks. They end by offering advice to a listener who’s having trouble getting the last guest to leave at the sex parties he throws.

Judson receives some unwanted attention. Brian has “the talk” with his 8 year-old. Then, Bob Levine, celebrating 69 years as both drag icon Rose Levine and as a denizen of Cherry Grove, sits down with Judson and Brian at the Belvedere Guest House for Men as he prepares for Rose's Green Room 42 debut next month. Subject of the documentary “Roseland: The Ballad of Bob Levine,” Bob lets Judson and Brian in on the secret to his happy life, and recounts seven decades of gay history through the lens of Fire Island. To close, a listener asks what tips for visiting the Island our Dad and Daddy might suggest for a first-timer who finds it intimidating.