Chelsea Handler says 50 Cent was one of the "sweetest people" she ever dated and discussed their brief relationship during an appearance on House Guest with Scott Evans. She revealed that the two met on her iconic talk show, Chelsea Lately, and started dating days later.
"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 said, as caught by Complex. "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.'"
When Did Chelsea Handler & 50 Cent Date?
50 Cent and Chelsea Handler's relationship began in the early 2010s. Further in her interview with Evans, she explained that she was scheduled to perform in New Orleans at the time and told 50 he was welcome to join her on the trip. "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. She recalled suggesting they go for a walk, despite 50 warning her that he might be too famous to do so. "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."
Handler concluded that they only dated for "a very short time," but recalled there still being plenty of public backlash. "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.
Chelsea Handler's interview with Scott Evans comes as she'll be performing across the United States for her High And Mighty tour in 2026. 50 Cent, on the other hand, just executive-produced the new documentary for Netflix, Sean Combs: The Reckoning.
