Jania Ashlynn
Chelsea Handler had a realization that it was time to call it quits with her ex-beau, Ted Harbert. When she decided to have a threesome with him and her masseuse.
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Trying New Things
Handler shared the story on Andy Cohen’s podcast Andy Radio. “I was very turned on by this woman,” Handler shared. She went on to clarify that she has “slept with a woman” but “hasn’t dated a woman.”
She continued: “I ended up hooking up with her several times without the guy.”
Handler, 48, found herself drawn to the unidentified masseuse in her threesome, causing her to realize that she was more interested in the masseuse than in Harbert. This realization ultimately led to the end of their relationship.
“That’s when I knew it was time to break up with the guy,” she shared.
The comedian had a four-year romantic fling with the ex-chairman of NBC Broadcasting, who is now 67-years-old. However, things between them eventually came to an end in 2010. The following year, the stand-up performer tied the knot with Lisa Medrano.
Handler didn’t inform Harbert that she was having an affair with the masseuse, but she did describe their threesome as “fun” and expressed her willingness to have another one.
“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 revealed that the thought of a man she’s currently seeing suggesting the addition of another guy to their relationship doesn’t sit well with her. It’s not something she’s particularly fond of.
She also expressed confusion with why her male partner would like to experience “penetration” with another man. “Maybe oral is less questionable. I don’t know,” Handler mused. “I’ve never been up against this kind of conundrum.”
Going Separate Ways
Handler has recently revealed that she is back to being single. Her one-year relationship with Jo Koy ended 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.
“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 shared that she was actively working through her trauma, but unfortunately, Koy, who is 52, was not willing to support her on this journey.
“I love him, and he’s on his own path. If I have to choose one person, I have to choose myself,” she continued.
She also added that neither of them cheated in the relationship, 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 shared.
