Comedian Ian Lara joins Lip Service for a brutally honest, hilarious conversation about sex, dating, money, and comedy.

Ian opens up about how Madonna personally approved his comedy special, why dating shifts when women make more money, and how real-life experiences — including getting circumcised at 15 — turn into some of his biggest jokes. He also breaks down the grind behind comedy success, the pressure of the industry, and why performing for small crowds can be harder than sold-out rooms.

The conversation covers dating red flags, modern relationship expectations, posting partners on social media, and why staying humble matters even after major wins like HBO and late-night TV.

A classic Lip Service episode: unfiltered, funny, uncomfortable, and real.