Chelsea Handler Reflects On What It Was Like Dating 50 Cent

NEW YORK, NEW YORK - SEPTEMBER 30: Curtis "50 Cent" Jackson visits "Fox & Friends" to discuss his new Fox Nation show "50 Ways to Catch a Killer" at Fox News Channel Studios on September 30, 2025 in New York City.
NEW YORK, NEW YORK – SEPTEMBER 30: Curtis “50 Cent” Jackson visits “Fox & Friends” to discuss his new Fox Nation show “50 Ways to Catch a Killer” at Fox News Channel Studios on September 30, 2025 in New York City. (Photo by John Lamparski/Getty Images)

Chelsea Handler is spilling the tea on what it was like to date 50 Cent.

Handler says she and 50 dated briefly in the early 2010s. While on House Guest with Chris Evans, Handler describes 50 as one of the “sweetest people” she’s ever dated.

Handler says the two met on her former talk show, and soon after began dating. “It was like a Friday that he was a guest, I think. And then I came in over the weekend and there were like dozens and dozens of roses in my office,” Handler explained. “And my assistant was like, ‘Curtis Cent has called three times.’ And I was like, ‘Who’s Curtis?’ She’s like, ‘Fiddy.’”

“He was sweet ’cause he seemed gangsta, but he wasn’t a gangsta,” Handler continued. “Like, the fact that he was shot so many times, you’re like, ‘How did you get shot? Like that doesn’t even make any sense.’”

Handler says she once had a show in New Orleans where she invited 50 to.  She explains, “he comes to the hotel. He checks in. And my assistant’s like, ‘Okay, well, now you’re really going to deal with him. And I was like, ‘Oh sh*t, what did I get myself into?’” Handler joked.

“Black people and everyone knew him and he’s like a major deal,” Handler recalled. “He came to my show. He was very sweet. He’s such a sweet guy and he doesn’t do drugs which was the biggest disappointment of all.”

Despite the relationship being short lived, Handler says she enjoyed it and ignored the backlash she got because of it. . “I don’t allow myself to get upset about things like that. But I think at that point in my career, people were just, like, I mean — it was just kind of racist, this backlash,” she said.


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