Chelsea Handler confirmed she’s single after about six months of dating her cowboy boyfriend, but she also revealed they’re still friends—and were seen together again over the weekend.
Chelsea Handler’s love life hit a familiar rhythm: a fun, fast romance—and then a clean cut that didn’t turn bitter.
The 51-year-old comedian confirmed she is now single after dating her cowboy boyfriend for about six months. sharing that they decided to go their separate ways. Speaking on the Let’s Be Honest with Kristin Cavallari podcast. Handler described how the relationship began. saying she met him in Vegas at a blackjack table.
“We had a great five, six months together,” she said.
In Handler’s telling, the breakup was amicable. Their split, she explained, was mostly driven by her own shifting interest as the relationship hit its six-month mark—exactly when she tends to feel ready to move on.
Even with the status change, Handler made it clear the cowboy boyfriend hasn’t been erased from her world. She said they remain friends, and recent social media offered a glimpse of that connection. The pair appeared back together just this past weekend.
She also attended the BottleRock Napa Valley festival, with Handler’s new Instagram post reflecting that they’re still in each other’s orbit. When Cavallari pressed for what happens next, Handler didn’t shut the door. “Maybe I’ll see him again, maybe we’ll fool around again,” she told Kristin.
Handler used the interview to address another potential misconception, too—photos she shared of him earlier this year. She said she wasn’t trying to signal anything serious, explaining that she posts men she’s dating all the time.
“I post guys all the time that I’m dating,” she said. “I’m not posting them saying, ‘this is my boyfriend.’ It’s like, who I’m spending time with.”
At this stage of her life, Handler said she doesn’t want a long-term relationship at all. She described a preference for something lighthearted—without commitments that come later.
“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,” Handler added.
The conversation also included a personal detail from Handler’s dating experiences, including the celebrity she name-dropped after a “blind date” experience.
For now, the story isn’t about a dramatic fallout—it’s about Handler’s boundary lines, and the way she keeps her door open for friendship (and maybe more) even after the label changes.
Chelsea Handler cowboy boyfriend split single Let’s Be Honest Kristin Cavallari podcast Instagram BottleRock Napa Valley dating six months