Chelsea Handler's Intriguing Love Life: Unraveling Her Romances with 50 Cent and Jo Koy

Chelsea Handler is known for her outspoken nature, and this extends to her personal relationships, including her romantic ones. Not shy to share her love for marijuana and the freedom that comes with not having children, the comedian is bold in discussing all facets of her life. In fact, she even candidly revealed to Andy Cohen in June 2023 that her breakup with ex-boyfriend Ted Harbert was a result of a threesome involving a masseuse.

"I found myself incredibly aroused by this woman," she reminisced during a Radio Andy interview, 13 years after her separation from Harbert. "I ended up engaging in multiple encounters with her, even while I was dating someone else. It was at that moment when I realized it was necessary to end things with my then-partner."

In 2021, the ex-host of Chelsea Lately disclosed that marriage may not be a possibility for her, despite her relationships with well-known comedians like Jo Koy and 50 Cent.

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"I'm not sure if I'm the type of person who wants to get married," she shared with NBC, hinting that her perspective might evolve in the future. "I always seem to contradict myself. Whenever I claim I won't do something, I usually end up doing it the following weekend, so I've decided to stop making such statements."

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

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

Chelsea Handler is known for her outspoken nature in various aspects of her life, including her romantic relationships. The comedian openly discusses her affinity for marijuana and the freedom that comes with not having children. Additionally, Handler has not shied away from discussing her sex life, revealing to Andy Cohen in June 2023 that her involvement in a threesome with a masseuse played a role in her breakup with former boyfriend Ted Harbert.

The woman's statement on Radio Andy, 13 years after her separation from Harbert, revealed that she was greatly attracted to this woman. They engaged in multiple encounters while she was still in a relationship with another man. It was at this point that she realized it was necessary to end her relationship with the guy. However, in 2021, the former host of Chelsea Lately disclosed that she may not pursue marriage, despite having notable relationships with comedian Jo Koy and 50 Cent.

"I'm not sure if I'm the type of person who wants to get married," she shared with NBC at that time, playfully hinting that she might have a change of heart in the future. "It's hard to say for certain, as I often find myself going back on my words. Whenever I claim I won't do something, I always end up doing it shortly after, so I won't make such declarations anymore."

Continue scrolling to discover Handler's romantic journey over the years.

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Ted Harbert

Handler and Harbert were in a relationship for four years before they ended things in 2010. While Handler admitted to Cohen that her attraction towards their third partner contributed to the breakup, she later revealed to Marie Claire in 2012 that their professional responsibilities also played a role in the split. (At the time, Harbert held the position of president at E! Entertainment while Chelsea Lately was still on the air.)

Upon returning from work, Ted would routinely ask, "Would you like to watch your show?" To which I would reply, "No, I just finished watching my show. That's the last thing I would want to do." Ultimately, this was the reason for our relationship not working out, I believe," she expressed at the time.

Credit: Desiree Navarro/WireImage

Dave Salmoni

Handler was romantically involved with the Animal Planet star in 2010. She casually mentioned their split during a monologue on Chelsea Lately that same year.

"I've made the decision to collaborate with other networks. I worked closely with Animal Planet until a few weeks ago, but regrettably, that contract came to an end," she cleverly remarked. "Nonetheless, I had a great time partnering with them and might occasionally collaborate on future projects."

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50 Cent

Handler had a short-lived romance with the rapper in 2011. "To be honest, I'm not sure if I can handle him. I enjoy having a good time and I'm determined to avoid getting too serious," she shared exclusively with We during that period.

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After twelve years, she referred to 50 Cent as her "preferred former partner".

"I have a great affection for 50 Cent, he was enjoyable to be around. He was genuinely kind and a delight to spend time with," she shared with Entertainment Tonight in January 2023. "My friends truly enjoyed his company as well. Although our romance was brief, lasting only two months, I would definitely share a drink with him if I ever saw him."

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Andre Balazs

Handler described her brief relationship with the businessman — whom she dated for roughly a year between 2011 and 2012 — as draining.

Handler discussed her challenges in maintaining a long distance relationship during an interview on Marc Maron's "WTF" podcast in 2012. She expressed how incredibly time-consuming and difficult it was for her to concentrate on anything. The constant back and forth between New York and Los Angeles drained her both physically and emotionally. Despite the exhaustion, Handler admitted a preference for long distance relationships as it allowed her to avoid dealing with someone on a daily basis. However, she acknowledged that the romance had a negative impact on her career and work, leaving her feeling drained and unable to focus.

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Jo Koy

When Handler finally got together with Koy in 2012 — after 20 years of friendship — even she thought she found The One.

"Do not compromise who you are or diminish yourself in your search for a partner. Have patience and refuse to settle for less than you deserve," she shared on Instagram. "The person meant for you may already be by your side, even if you haven't realized it yet." Despite numerous affectionate Instagram posts and professions of love from both parties, the couple ultimately ended their relationship in July 2022.

"We had disagreements over certain behaviors, and it seemed like I would have to sacrifice my true self – something I might have been willing to do in my younger years, but not anymore," Handler later explained to Brooke Shields. "No matter how much I cared for this person, and I cared deeply, I refused to lose sight of who I am. I wasn't willing to change myself to make them more comfortable. I made the difficult decision to walk away from what I believed could have been a lifelong partnership."