Chelsea Handler is opening up more about her brief early-2010s romance with 50 Cent.
The comedian revisited their relationship during her appearance on Scott Evans’ House Guest. Around the 46-minute mark, she joked that Fif actually “convinced” her to date him.
Handler explained that 50 asked her out after appearing on her former E! show. “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,” she told Evans. “And my assistant was like, ‘Curtis Cent has called three times.’ And I was like, ‘Who’s Curtis?’ She’s like, ‘Fiddy.’”
She noted that plenty of celebrity men had tried to hit on her before, and at first she almost ignored him. But Fifty eventually won her over. “He was sweet ’cause he seemed gangsta, but he wasn’t a gangsta,” Handler said. “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 said she invited 50 Cent to her stand-up show in New Orleans that same weekend so they could grab a drink afterward. “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 shit, what did I get myself into?’” she joked.
She suggested they take a walk, but The Massacre rapper tried to warn her they’d get mobbed by fans — which is exactly what happened.
“Black people and everyone knew him and he’s like a major deal,” Handler said. “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 said they only dated for “a very short time,” and that the situation “blew up” because people didn’t understand their chemistry.
She also touched on the “backlash” their brief romance sparked. “I don’t allow myself to get upset about things like that. But I think at that point in my career, people were just… I mean — it was just kind of racist, this backlash,” she said.
Earlier this year on Call Her Daddy, Handler also shared that she once bought a “chocolate Bentley” to impress Fifty before realizing artists often rent flashy cars.
