May27 , 2026

    Chelsea Handler Confirms Split From Cowboy Boyfriend, Reunites With Him as Friend

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    Credit: Instagram

    Chelsea Handler has confirmed she is now single!

    The 51-year-old comedian was dating her cowboy boyfriend for about six months before they decided to go their separate ways, she revealed in a new podcast interview.

    However, they were seen back together just this past weekend!

    While appearing on the Let’s Be Honest with Kristin Cavallari podcast, Chelsea opened up about the split.

    “The last guy I was dating, I met him in Vegas at a blackjack table. That was a really fun, like, adventure,” she dished. “We had a great five, six months together.”

    Chelsea says their breakup was amicable and mostly driven by her lack of interest in a long-term relationship, admitting around the six month mark is when she typically feels ready to move on.

    While they broke up, she did say that they remain friends, and that was evident in a new Instagram post, where they attended the BottleRock Napa Valley festival.

    “Maybe I’ll see him again, maybe we’ll fool around again,” Chelsea told Kristin.

    The comedian also clarified that sharing photos of him earlier this year publicly wasn’t meant to signal anything serious.

    “I post guys all the time that I’m dating,” she says. “I’m not posting them saying, ‘this is my boyfriend.’ It’s like, who I’m spending time with.”

    At this point in her life, Chelsea is not interested in a long-term, committed relationship, preferring a lighthearted and uncomplicated romance instead.

    “I am not a long-term person. I’m not interested in anything that comes after the six-month relationship mark,” she shared. “I’m not interested in dealing with your family or your issues. I am not interested.”

    “I don’t want to be part of a unit. I want to have a good, sexy affair. I don’t want to be a couple,” Chelsea adds.

    Also during the interview, Chelsea name-dropped the celebrity she had a bate date experience with.

    Posted To:Chelsea Handler Split





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