Chelsea Handler's Dating History: From 50 Cent to Jo Koy

Chelsea Handler is outspoken about all areas of her life — and her romantic relationships are no exception. The comedian frequently gets real about her penchant for weed and the luxury of living a child-free life. Handler has also been open about her sex life, telling Andy Cohen in June 2023 that a threesome with a masseuse led to her split from ex-boyfriend Ted Harbert. “I was very turned on by this woman,” she recalled on Radio Andy 13 years after her split from Harbert. “I ended up hooking up with her several times without the guy that I was dating. That’s when I knew it was time to break up with the guy.” In 2021, the former Chelsea Lately host revealed that marriage might not be in the cards for her, despite high-profile romances with fellow comedian Jo Koy and 50 Cent. “I don’t know that I’m the marrying kind,” she told NBC at the time before teasing that she might change her mind down the road. “I feel like, who knows, I doubt it, but usually when I say I’m not going to do somet

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Chelsea Handler's Dating History: From 50 Cent to Jo Koy

Chelsea Handler is outspoken about all areas of her life — and her romantic relationships are no exception.

The comedian frequently gets real about her penchant for weed and the luxury of living a child-free life. Handler has also been open about her sex life, telling Andy Cohen in June 2023 that a threesome with a masseuse led to her split from ex-boyfriend Ted Harbert.

“I was very turned on by this woman,” she recalled on Radio Andy 13 years after her split from Harbert. “I ended up hooking up with her several times without the guy that I was dating. That’s when I knew it was time to break up with the guy.”

In 2021, the former Chelsea Lately host revealed that marriage might not be in the cards for her, despite high-profile romances with fellow comedian Jo Koy and 50 Cent.

“I don’t know that I’m the marrying kind,” she told NBC at the time before teasing that she might change her mind down the road. “I feel like, who knows, I doubt it, but usually when I say I’m not going to do something, I end up doing it like the next weekend, so I’m not going to say that anymore.”

Keep scrolling to see Handler’s love life throughout the years:

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