Chelsea Handler is sharing insight into her previous relationship with 50 Cent.
“He convinced me to date him after he was on my show,” Handler, 50, told Scott Evans during the December 5 episode of his “House Guest” podcast. “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.”
The comedian added that her assistant told her, “Curtis Cent has called three times.” (The 50-year-old rapper’s real name is Curtis James Jackson III.)
“I was like, ‘Who’s Curtis?’” Handler continued. “She’s like, ‘Fiddy.’”
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Handler said her assistant told her that 50 Cent wanted to call her, but that she didn’t want to talk to him.
“All those guys used to hit on me,” Handler explained. “But Curtis was sweet.”
Handler joked that she didn’t know how 50 Cent was “shot so many times” because of his sweet nature. (The “In da Club” rapper was shot nine times at close range outside of his grandmother’s home in Queens, New York, in 2000, resulting in multiple injuries.)
“So then I was like, ‘Listen, I’m not going out with you,’” she recalled telling 50 Cent. However, she did invite him to see one of her comedy shows in New Orleans and said they could grab a drink afterward.
“He’s a very sweet guy and he doesn’t do drugs, which was the biggest disappointment of all,” Handler joked. “And we only dated for a very short time, but you know, people it blew up because people were like, ‘What are these two doing together?’ But he really was one of the sweetest people.”
Handler and 50 Cent briefly dated in 2011.
“I don’t know if I can handle him, to be honest. I like to have fun, and I’m really trying to not get into anything too serious,” the Chelsea Lately star exclusively told NewsPlop at the time.
Handler later called the Den of Thieves actor her “favorite ex.”
“I love 50 Cent, he was fun. He was just a sweetheart and he was fun to be around,” she told Entertainment Tonight in January 2023. “My friends loved hanging out with him. I loved hanging out with him. It was a pretty short-lived romance, it was only two months. But yeah, I mean, If I saw him I’d definitely have a drink with him.”
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Handler also opened up about her relationship with 50 Cent during her appearance on Alex Cooper’s “Call Her Daddy” podcast earlier this year, revealing why her friends loved him so much.
“All my friends, when I dated him, just f***ing loved it, because he’d come over to our house every night and he’d have like a Lamborghini one day and then like a yellow Ferrari the next day,” she explained. “Meanwhile, I realized he was borrowing all these cars from different dealerships. I was like, ‘You can do that?’ You know? I’m like, ‘Oh.’”
Handler said she then went out and got her own luxury car.
“I got a Bentley. I got a chocolate Bentley because he kept coming over every night, and he had a different car, so as a joke, I went and bought a chocolate Bentley,” she continued. “I didn’t know you could borrow cars as a celebrity. So I went and bought a chocolate Bentley and then we broke up. So there I am stuck with this chocolate Bentley like a f***ing white dumb bitch a**hole driving around like I’m some rapper and I had that Bentley, which was a really nice car, by the way, I had that Bentley for like two years.”