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Chelsea Handler's relationship ended after a threesome. But not for the reason you may think.

Comedian Chelsea Handler is getting real about her relationship with Ted Harbert. 

Handler dated the American businessman for four years before calling it quits in 2010 and now she's explaining just why she chose to end their relationship.

Speaking on Andy Cohen’s SiriusXM show, Andy Cohen Live, Handler shared that she called it quits with Harbert after the couple had a threesome with their masseuse.

But it wasn't because of jealousy like you might think. 

And it wasn't because she didn't enjoy the sex, either.

Watch Mamamia Confessions: Relationship Dealbreakers. Post continues after video. 


Video via Mamamia. 

In fact, Handler enjoyed the sex with her masseuse very much – and her masseuse only.

"I was very turned on by this woman," she said, clarifying that she has "slept with a woman" but "hasn’t dated a woman".

"I ended up hooking up with her several times without the guy," she later added.

The sexual encounter resulted in an awakening for Handler, who realised that she actually enjoyed having sex with her masseuse more than her partner. 

Handler abruptly ended the relationship a short while later. 

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

Handler dated Harbert from 2006 until 2010. He married Lisa Medrano, a former human resources exec, the following year. 

Chelsea Handler and Ted Harbert, 2008. Image: Getty.

Handler admitted she never told the TV executive that she continued 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 explained. "You know? She can do all the stuff that I’m too f**king lazy to do."

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Handler also admitted she would "question" if her male partner wanted to have a threesome with a man, saying the idea of him having "penetration" with another man confused her.

"Maybe oral is less questionable. I don’t know," the comedian pondered. "I’ve never been up against this kind of conundrum."

Handler most recently dated American comedian Jo Koy for a year before the pair announced their split on Instagram. 

Chelsea Handler and Jo Koy, 2022. Image: Getty.

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She shared later on the podcast Now What? With Brooke Shields, that it became clear he "was not my person".

"I just discovered some stuff. I discovered that there were just behaviours that I felt that we couldn't agree on," she shared. 

"It felt to me like I would have to abandon myself, which maybe I would have been okay to do if I were 20 or 25, but I wasn't willing to do that. No matter how much I loved this person – and I loved him so much – I was not going to abandon myself."

Listen to Sealed Section, Mamamia's sex podcast hosted by sexologist Chantelle Otten. Post continues after audio. 


Handler also told Glennon Doyle on the podcast We Can Do Hard Things that their breakup was eye-opening. 

"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 said.

"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 also emphasised that neither had cheated; it simply "didn’t work out" between them.

"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," she explained. 

"This is the first time that I’ve ended a relationship where I’ve felt like an adult."

Feature Image: Getty/Mamamia.

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