Chelsea Handler Recalls How 50 Cent ‘Convinced’ Her To Date Him, ‘Don’t Know If I Can Handle Him…’

Chelsea Handler recently sat down with Scott Evans, host of the House Guest podcast, and revealed how 50 Cent convinced her to date him. The comedian and actress is immensely loved for her stand-up and acting. Chelsea is known for her stints in Will and Grace, The Practice, Not Dead Yet, Cattle Call, and the Chelsea Handler franchise.

Chelsea Handler reflects on how 50 Cent convinced her to date him

Chelsea Handler recently appeared on the House Guest podcast and talked about several developments in her professional and personal life. However, it was the stand-up comic’s insight into her previous relationship with 50 Cent that caught everyone’s attention. Chelsea was quoted as saying:

“He convinced me to date him after he was on my 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. My assistant said, ‘Curtis Cent has called three times.’ I was like, ‘Who’s Curtis?’ She’s like, ‘Fiddy.'”

In the same conversation, Chelsea Handler revealed that 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.” Chelsea even joked that she didn’t know how 50 Cent was “shot so many times” because of his sweet nature. While she told Cent that she won’t go out with him, the comedian invited him to see one of her comedy shows in New Orleans and said they could grab a drink afterward. She was quoted as saying:

“He’s a very sweet guy, and he doesn’t do drugs, which was the biggest disappointment of all. 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.”

Chelsea Handler on her brief relationship with 50 Cent

Chelsea Handler and 50 Cent briefly dated in 2011. During a conversation with Us Weekly a while back, she called Cent her ‘favourite ex’. She added that he was such a sweetheart and fun to be around during a 2023 conversation with ET. She revealed her friends loved hanging out with Cent, and even she loved hanging out with him. She said, “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.” 

Chelsea Handler bought a Bentley in a relationship with 50 Cent

Chelsea Handler also opened up about her relationship with 50 Cent during her appearance on Alex Cooper’s Call Her Daddy podcast earlier in 2025. She revealed her friends loved Cent a lot because he’d “have like a Lamborghini one day and then like a yellow Ferrari the next day.” She added that she soon realised he was borrowing cars from different dealerships, and then went out and bought her own luxury car. She added:

“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 one. 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.”

What are your thoughts on Chelsea Handler’s revelations? 

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