Chelsea Handler recently spoke candidly about her experiences with dating as she advances in age. On March 27th, the 51-year-old comedian and actress appeared on the IRL podcast with host Angie Martinez, where she delved into her romantic life and evolving preferences.
During the conversation, Handler revealed that despite currently being in a relationship with a man 14 years her junior—whom she met at a Las Vegas casino—she avoids structuring her life around a partner. When Martinez asked if the age gap ever posed challenges, Handler admitted she initially hesitated to date someone younger but ultimately does not let it affect her emotionally.
Reflecting on her past, Handler shared that in her 20s and 30s she typically dated older men, often significantly older. She explained, “When I was in my 20s, I dated men 20 years my senior; in my 30s, I dated men in their 50s.” However, this pattern shifted as she reached 40, deciding to no longer date men in their 60s. She humorously noted, “I’ve got to flip it and reverse it. Now I’m heading in the opposite direction because I’m too hot to be dating a 65-year-old. Let’s be honest.”
Handler emphasized her commitment to maintaining independence, stating, “I don’t work this hard on myself and take such good care of myself so that I can’t have fun and have a good time. I enjoy traveling and casual relationships but prefer to avoid anything too serious or someone constantly in my space.” Notably, she regards marriage as an outdated institution and has previously been linked to well-known personalities such as 50 Cent, Jo Koy, Ted Harbert, Dave Salmoni, and Ralph Fiennes.
