Chelsea Handler gets honest about dating in her 50s

2026-03-27 - 09:30

Chelsea Handler recently opened up about her dating life and how advancing age impacted it. On March 27th, Handler appeared in the episode of the IRL podcast, where she sat with host Angie Martinez and talked about her romantic life. As the conversation went deeper, the 51-year-old American comedian and actress revealed why she avoids building her life around a partner despite having a relationship with a 14-year-old younger man, whom she first crossed paths with at a casino in Las Vegas. Martinez inquired if she ever felt the age gap between them was a negative aspect of their relationship, to which she admitted that she was not ready to date someone younger than her; however, she doesn’t “really feel anything” about it. She further told, “When I was young, 20s, 30s, I always dated older guys. 20s, like 20 years older than me. I always dated 40-year-olds when I was 20, 50-year-olds when I was 30”. Lifestyle News – Latest Entertainment News, Celebrity Gossip The visible change in her preferences came when she turned 40 and made a firm decision not to date 60-year-old men. Handler noted, “Like, I’ve got to flip it and reverse it, you know? So, now I’m heading in the opposite direction because I’m too hot to be dating a 65-year-old. Let’s be honest”. The Girls Behaving Badly star confessed, stating that she prioritises her independence, “I mean, I don’t work this hard on myself and take such good care of myself so that I can’t have fun and, you know, have a good time. I like travelling a lot. I like hooking up with guys. I don’t like to get too serious. I don’t want someone in my space all the time”. It is important to note that Chelsea Handler, who considers marriage an “outdated” practice, has been in relationships with notable figures such as 50 Cent, Jo Koy, Ted Harbert, Dave Salmoni, Ralph Fiennes, and others.