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Chelsea Handler is dishing all the dirt surrounding her relationships with famous men.
In a recent interview on Kristin Cavallari’s podcast, “Let’s Be Honest,” the 51-year-old comedian shared she once went on a date with an unnamed famous A-List actor, noting “he was so boring.”
“We were flirting, and then I made the move,” she explained. “So I made the move, and he was receptive, and we were hanging out, and I saw him, and we went on a date, and it was unbearable. And I worked hard.”
She went on to explain that part of the problem was that “he was so serious about himself as an actor” and spent a lot of time “talking about acting in a way I can’t take seriously.”
Handler shared she went on a date with an A-List actor, who she called “boring” and “unbearable.” (Kevin Mazur/Getty Images for Netflix)
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Handler said that “he was very much about himself and his process and his acting,” and after carving out time in her schedule to meet with him while abroad, Handler ended the date disappointed with the outcome, saying “he didn’t ask me one question about myself.”
“I felt like I was 25 years old and had to like make up a lie you know to get away cause I had really pursued him, but then so once I sat down with him I was like no,” she said. “Immediately I was like you’re so boring and you’re so annoying – like anyone who talks about themselves for that long on a date is just that’s exactly what’s wrong with men.”
Earlier in the interview she also shared that she “had a nice little affair” with a well-known celebrity for a few months, but also refused to name that star.
During a recent appearance on the “Howie Mandel Does Stuff” podcast, Handler commented on the current dating culture, noting, “It’s very hard in today’s world to meet straight guys that have their s— together.”
Handler recently slammed the current dating culture, blaming dating apps for creating unlimited options. (Leon Bennett/GA/The Hollywood Reporter)
“So, I was initially trying to help straight women meet straight men,” she explained. “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.”
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When speaking about her own love life, Handler told the “Not Skinny But Not Fat” podcast in January that she “love[s] all drugs,” and whoever she dates needs to as well.
Handler then went on to explain that she and her friends often gather at parties and measure out the different drugs. When asked if she could be friends or date someone who is sober, Handler says she tries not to.
“No. Like if I’m gonna date a guy, they’re gonna have to party,” she said. “I wanna party. I like to get loose. And by the way, I’m 50 years old. Years. Years. I’m a perfect shining example of drugs being an enhancement to my life. Yeah. Like what, what are you gonna say? I’m a mess. I’m a loser. I don’t have it together? I do.”
Handler explained she is not trying to chase men and called marriage an “outdated” idea. (Kevin Winter/Getty Images for Critics Choice Association)
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Most recently, Handler was in a public relationship with comedian Jo Koy, who she dated for around one year from 2021 to 2022, telling the “Now What?” podcast in December 2022 she decided to end the relationship after “it just became clear that this was not my person.”
While she is currently dating someone, the former “Chelsea Lately” host said on the “Angie Martinez IRL Podcast,” that she thinks marriage is “outdated” and that she prioritizes her freedom.
“I’m here for women, and I’m here for myself,” she said. “I’ve never been very thirsty for a man or a partner. You’ve got to really kind of get my attention for me to pay attention in a serious way, because otherwise it’s a bunch of casual encounters. You know what I mean? I like that. 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. I just am not interested in that.”
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