Chelsea Handler Recalls Threesome With Her Masseuse and How It Caused Her Breakup

The comedian shared the deets on Andy Cohen's SiriusXM show.

Chelsea Handler is revealing the real reason that ended her four-year relationship with Ted Harbert, the former NBC Broadcasting chairman who was president of E! Entertainment when the comedian's late-night show premiered in 2006.

On Wednesday, the 48-year-old comedian spoke to Andy Cohen on his SiriusXM show where she was asked if she had ever dated a woman. Handler answered by saying she had "slept" with a woman but never dated one. This, of course, led Cohen to ask a series of follow-ups, such as wondering whether this was a one-off situation.

"It was like a threesome," she responded.

When asked how it went, Handler said it was "fun" and that she "would for sure" do it again should the opportunity arise. Handler would go on to reveal that the woman who joined her and her then-boyfriend for a threesome was none other than the couple's masseuse.

"I was very turned on by this woman. I ended up hooking up with her several times without the guy that I was dating," Handler revealed. "That's when I knew it was time to break up with the guy."

Handler and Harbert began dating in 2006, the same year The Chelsea Handler Show premiered on E! Network. Just months after they began dating, they moved in together. But in 2012, Handler told Marie Claire that the reason why they broke up was because Harbert couldn't keep business separate from their relationship.  

"I would come home from work, and Ted would be like, 'Do you want to watch your show?' and I'd be like, 'No, I just came from my show. That's the last thing I'd want to do,'" she told the outlet. "That was the reason it didn't work out, ultimately. I think."

Fast-forward to now, and Handler admits the threesome may have actually led to the breakup. What's more, Handler says her hookups with the masseuse without Harbert is something she never revealed to him.

"I don't think I ever revealed that, but I mean, hopefully, he's listening now," she quipped. "His name is Ted Harbert. He's in Portugal though. He might not have access to this ... he and his wife are building a house in Portugal."

For the record, Handler, who most recently dated comedian Jo Koy for nearly a year before their June 2022 split, said if she were ever in a relationship she would "absolutely" gift her man a three-way.

"It's fun," she added.

In the same interview, Cohen also wondered if it ever bothered Handler that some speculated that she found success on E! Network because she was dating the boss.

"Not really because, I mean, it doesn't matter if it's not true. Like, obviously I've had a career now for like 25 years," she said. "I don't really care if anyone thinks that."

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