NEWS'Casual Lover' Chelsea Handler Admits She Doesn't 'Like to Be Tethered to 1 Person' Amid Fling With Younger Guy

'I wouldn’t say I’m in a relationship,' Chelsea Handler spilled.
May 14 2026, Updated 3:39 p.m. ET
Chelsea Handler isn't afraid to spill on her untraditional dating life.
On the Tuesday, May 12, episode of the "Howie Mandel Does Stuff" podcast, the comedian explained why she started playing matchmaker on social media and dished on her own relationship status.
Is Chelsea Handler Single?

The comedian admitted she's a 'casual lover' who prefers to not exclusively date one person.
"I wouldn’t say I’m in a relationship," the star revealed. "I would say I’m dabbling in different areas of my life. I don’t like to be tethered to one person."
"I am a casual lover. So, I find my men in casual," Handler continued, noting she met her "last guy" in Las Vegas while gambling.
Despite not being serious, the former late-night host has shared a few pictures with the younger guy, who even flew to Antartica to hangout with her.
'Something's Wrong'

The comedian feels there's been a 'cultural shift' in dating.
While Handler, 51, isn't looking for a long-lasting romance herself, she knows plenty of people who are.
"It's very hard in today’s world to meet straight guys that have their s--- together," she insisted. "Something’s wrong. I don’t know what’s wrong."
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Chelsea Handler has been casually seeing a younger guy she met in Las Vegas.
"I was initially trying to help straight women meet straight men," she said of using her Instagram page to help single people connect. "But I think with dating apps and social media, there’s just so much abundance and so much choice that nobody really feels like they have to lock it in. They can swipe through 50 women a day, so they’re not making the effort that people used to make to date."
Chelsea Handler said countless men are 'emasculated' by an independent and successful woman.
Handler said she knows numerous "incredible" women who complain to her that there's no "men out there."
"Men are feeling attacked. They can't deal with women's success or women's independence. They don't like that. Not every guy is OK with that. It's emasculating," she said. "So, it's like a shift. We're going through like a culture shift it feels like."
The Star Isn't Interested in Getting Married

The star sees marriage as a 'very patriarchal thing.'
Though the author has never been interested in getting married since it's a "very patriarchal thing," she admitted on an episode of the "IRL With Angie Martinez" podcast that she will never say never.
"It's not something I attain to do... but since I've bemoaned marriage my whole entire public life, it would be really hypocritical for me to get married, which means I'll probably do it," she quipped. "At some point I might just go, OK, f--- it. I'm 50 years old, so I might as well just go get married. What could go wrong at this point?"


