Chelsea Handler reveals how ‘threesome’ ended her relationship

Comedian Chelsea Handler has revealed the surprising way a threesome ended her long-term relationship – and it’s not why you’d think.

Chelsea Handler. Picture: Alberto E. Rodriguez/Getty Images

Chelsea Handler realised she had to break up with her ex-boyfriend Ted Harbert after having a threesome with him and her masseuse.

“I was very turned on by this woman,” the comedian told Andy Cohen of the massage therapist during Wednesday’s episode of SiriusXM’s Andy Radio, clarifying that she has “slept with a woman” but “hasn’t dated a woman”.

She added, “I ended up hooking up with her several times without the guy,” reports Page Six.

The ménage à trois caused Handler, 48, to realise she was more into the unidentified masseuse than Harbert, which ultimately led to the demise of their relationship.

“That’s when I knew it was time to break up with the guy,” she said.

The stand-up star dated the former TV executive, now 67, for four years before calling things off in 2010. He married Lisa Medrano the following year.

Handler admitted she never told Harbert that she was sleeping with the masseuse on the side, but she called their threesome “fun” and said she would have one again.

“I don’t want to get double-teamed by a guy, but I would like another girl in the situation,” she said. “You know? She can do all the stuff that I’m too f**king lazy to do.”

Handler and Harbert broke up after a threesome. Picture: Jesse Grant/Getty Images

Handler shared that she doesn’t love the idea of a man she is dating wanting to add another guy into the equation.

The former Chelsea Lately host also said that she would “question” why a male partner would want to have “penetration” with another man.

“Maybe oral is less questionable. I don’t know,” she pondered. “I’ve never been up against this kind of conundrum.”

The former TV host spoke frankly about her love life. Picture: Mark Davis/Getty Images

Handler is seemingly single after revealing that she ended her one-year relationship with Jo Koy in July 2022.

“It’s nice to bend for people. It’s nice to learn how to compromise. It’s nice to learn how to demonstrate my love publicly. … I believe Jo needed that,” she shared on the We Can Do Hard Things with Glennon Doyle podcast after their split.

“I was so inspired by us, but Jo didn’t crack me open. My psychiatrist cracked me open, and then I was open, and then I was able to bend for somebody. …. But you can’t change somebody intrinsically.”

Handler said she was working on processing her trauma in therapy but Koy, 52, wasn’t willing to follow her on her journey.

“I love him, and he’s on his own path. If I have to choose one person, I have to choose myself,” she added.

Handler also emphasised that neither had cheated and that it “just didn’t work out”.

“I did everything I could to make it work, but it didn’t work out. I wanted to make sure that everybody knew that this is a different me. This is the first time that I’ve ended a relationship where I’ve felt like an adult,” she said.

It seems that this time around, she ended her relationship for her therapist instead of her massage therapist.

This article originally appeared in Page Six and was reproduced with permission

Originally published as Chelsea Handler reveals how ‘threesome’ ended her relationship