Chelsea Handler Reveals Membership in the “Surprise, a Three-Way and Subsequent Hookups With a Masseuse Led to a Breakup” Club

Let’s play a counting game, shall we?

One: There is one comedian named Chelsea Handler. 

Two: Two people are in a romantic relationship: Handler and former NBC Broadcasting chairman Ted Harbert. (Ed note: This was back from 2006 to 2010, but let’s not get carried away with such large numbers just yet.) 

Three: Handler and Harbert had a threesome with their female masseuse. 

Several: Handler hooked up with the masseuse several more times after their initial encounter, which is “when I knew it was time to break up with the guy,” Handler told Andy Cohen on his SiriusXM radio show Thursday.

OK, so maybe we skipped a few digits, but the premise is there, right? 

Handler, 48, dropped the decade-old tea when Cohen asked her if she’d ever dated a woman. “I’ve slept with a woman, but I haven’t dated a woman, no,” she responded. She then explained that she’d had a threesome with her boyfriend at the time and another woman, calling it “fun” and said, “I was very turned on by this woman, I ended up hooking up with her several times without the guy that I was dating.” She then realized that it was probably not such a great sign for her relationship that she was more attracted to the guest star than her then-boyfriend. 

She then named Harbert specifically as the boyfriend in question, before saying that she hadn’t told him that she’d hooked up with their masseuse beyond the threesome. 

“I don’t think I ever revealed that, but hopefully he’s listening now,” she said, then casually discussed how she’s pretty sure Harbert and his wife are in Portugal, building a new house. 

Handler began hosting her E! talk show, Chelsea Lately, in 2007, then later began dating Harbert, who was technically her boss as the head of the network umbrella. In 2012, she told Marie Claire that she and Harbert had broken up because they couldn’t separate work and pleasure. 

“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 said. “That was the reason it didn’t work out, ultimately. I think.”

And as for those who share late comedian Joan Rivers’ belief that Handler “made it on her back, fucking the president…of the network,” as she said in 2012 on a Howard Stern appearance, here’s another thing you can count on: Handler doesn’t care.

“Not really,” Handler said to Cohen when asked if the speculation bothered her. “That stuff doesn’t matter if it’s not true. Obviously, I’ve had a career now for like 25 years, I don’t really care if anyone thinks that.”

VF wasn’t able to reach Harbert for comment and NBC did not immediately return a request for comment.