NEWSChelsea Handler Reveals How She First Started Dating 'Sweet' 50 Cent: 'What Did I Get Myself Into?'
Chelsea Handler called 50 Cent 'sweet' and a 'gangsta.'
Dec. 9 2025, Published 4:40 p.m. ET
Chelsea Handler opened up about her relationship with 50 Cent and how their unusual pairing went down.
The comedian, 50, discussed her past love affair with the G-Unit rapper, also 50, joking that he "convinced" her to date him back in the early 2010s.
Chelsea Handler and 50 Cent Met in the Early 2010s
Chelsea Handler and 50 Cent dated in the early 2010s for a brief period of time.
Handler recently appeared on an episode of House Guest where she described how her fling began.
50 was a guest on her E! talk show Chelsea Lately back in the day, and he sent her flowers after his appearance.
"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 host Scott Evans.
The Comedian Said the Rapper Was 'Gangsta'
50 Cent was a guest on her E! talk show 'Chelsea Lately' back in the day.
"And my assistant was like, 'Curtis Cent has called three times.' And I was like, 'Who's Curtis?' She's like, 'Fiddy,'" she recalled.
"He was sweet 'cause he seemed gangsta, but he wasn't a gangsta," the funnywoman noted. "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 then invited him to her comedy show in New Orleans at the time during one weekend — and the rest is history.
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The rapper and the comedian's relationship earned backlash.
She also invited him to get a drink with her after the show. "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 s---, what did I get myself into?'" Handler quipped.
Handler then asked the "In Da Club" singer to go for a midnight stroll with her, however, he was apprehensive due to the amount of wild screaming fans that would swarm him.
"Black people and everyone knew him and he's like a major deal," the Are You There, Chelsea? producer 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."
Chelsea Claimed People Were Racist About Their Romance
The couple's romance 'blew up' at one point.
Despite the relationship only lasting "a very short time," she felt that their romance "blew up" because people were unsure of what to make about their chemistry.
She noted how the couple received "backlash," adding, "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."
