Chelsea Handler Spills Secrets Playing “Who’d You Rather?”

Comedian Chelsea Handler joins the Modern Wisdom podcast for a candid and often humorous discussion about her dating life, culminating in a playful game of “Who’d You Rather?” Handler, who is currently single, begins by articulating a strong stance on the empowering nature of singledom, emphasizing the importance of treasuring independence rather than constantly seeking a relationship. She asserts that she enjoys not being “tethered to somebody” and encourages women to embrace their individual journeys, actively focusing on what they have rather than what they lack.

Handler, self-professedly “promiscuous,” shares her highly unconventional approach to dating, stating she is “open” to sleeping with someone on the first night. She frames this as a practical and efficient strategy, explaining, “I mean, that’s a quick way to find things out.” She prefers to assess chemistry and compatibility immediately, rather than enduring a potentially awkward two-hour dinner only to discover a lack of connection, noting, “I’d rather have that happen and then find out like then then I know if we have anything to talk about at a 2-hour dinner, not do the dinner first.” This informal approach, she says, allows for “nice accidents” to happen without the pressure of a traditional dating setup.

The bulk of the episode centers around a rapid-fire game of “Who’d You Rather?” designed to pinpoint Handler's ideal partner. She makes quick work of initial choices, consistently picking Chris Martin over names like Michael B. Jordan and Lenny Kravitz (who she humorously notes “already happened”). Her preferences shift as the game progresses; she rejects Harry Styles due to his youth, calling it “like a molester move,” and expresses a clear affinity for “older men,” leading her to consider Richard Gere. The game ultimately narrows her choices through a series of celebrity match-ups, with Handler weighing factors like age, appearance, and perceived personality.

After contemplating Idris Elba, The Weeknd, and Prince Harry (dismissing him with “I’m not into redheads”), Handler ultimately lands on John Stamos as her preferred celebrity partner, noting that he “likes to party” and is “age appropriate.” Though she briefly misses Richard Gere, she expresses satisfaction with Stamos, humorously anticipating a future setup. Listeners gain an intimate, unfiltered look into Chelsea Handler’s unique personality, her pragmatic yet playful take on modern dating, and her specific (and often surprising) romantic tastes.