Chelsea Handler, 51, isn’t sticking to traditional dating expectations, especially when it comes to age.
On Thursday’s episode of the “IRL podcast,” the comedian spoke about dating and the reason she doesn’t want to build her life around a partner.
Handler told host Angie Martinez that she’s seeing a man 14 years her junior, whom she met at a casino in Las Vegas. When asked about their age gap, Handler said she doesn’t “really feel anything” about it, but added that she initially wasn’t looking to date someone younger.
“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,” Handler said.
But when she turned 40, she began rethinking that pattern, and decided she didn’t want to date 60-year-olds.
“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,” Handler said. “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.”
She added that once she got to know the man she’s been seeing better, that “age thing went out the window.”
Still, Handler said she values her independence.
“I like traveling 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,” she said.
She added that her “whole vibe” is about freedom. Even though she sees marriage as “outdated,” Handler said she’d do it for the irony.
“But, you know, since I’ve bemoaned marriage my whole entire public life, I would be really hypocritical for me to get married, which means I’ll probably do it,” Handler said.
Handler has long been candid about her approach to dating.
During an appearance on “Call Her Daddy” in February 2025, Handler said she prefers to live life on her own terms.
“I’m not interested in long-term commitments, to work, to people, to anything. I am a free spirit and I want to remain and soar like an eagle,” she told host Alex Cooper.
She isn’t the only Hollywood star who has embraced relationships with younger partners.
In 2024, Cher said she prefers to date younger men because older ones are often intimidated by her. The singer has a 40-year age gap with her boyfriend, Alexander Edwards.
In 2025, Tracee Ellis Ross said she dates younger men because men her age are often “steeped in toxic masculinity.“
“And anything that starts to smell of that for me — I did enough of it where I was controlled and felt like I was a possession or a prize — I just have no interest in it. And I will not do it again,” Ross said.
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