Take Your Jeans Off w/ Rick Glassman | Your Mom's House Ep. 857

In this episode of Your Mom's House, Tom Segura welcomes comedian Rick Glassman for a raucous, boundary-pushing conversation that veers from sexual innuendo to cultural commentary. The duo dives into taboo topics like nipple and ball play, with Glassman sharing personal insecurities about his left testicle and his openness to unconventional sexual experiences in hypothetical scenarios. They explore the absurdity of online content, including extreme kinks and viral videos, while debating the ethics of sharing such material. Glassman also shares a poignant story about a fleeting, unspoken connection with a beautiful Asian woman at a Denver comedy show, turning it into a public plea for a missed romantic opportunity. The conversation shifts to broader themes—Jewish identity in comedy, the algorithmic obsession with certain content, and the performative nature of online personas. Throughout, the hosts blend crude humor with genuine vulnerability, reflecting on regret, connection, and the strange ways people seek intimacy in the digital age.