Comedian, actress, and host Chelsea Handler is recalling the once upon a time story of her dating rapper 50 Cent, revealing how he “convinced” her to date him 15 years ago and what the “biggest disappointment” was once they were in a relationship.
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While appearing a recent episode of Scott Evans’ ‘House Guest’ podcast, Handler, 50, recalls shocking fans everywhere when she became romantically linked to 50 Cent, real name Curtis Jackson, 50. The two started dating after he appeared on her show, ‘Chelsea Lately,’ in 2009 on E!
The two would then split in 2010. However, they have remained amicable ad things have always been positive between the two. In August 2020, Handler even gave a shoutout to her “favorite ex.” She took to her Instagram with a photo of them at a dinner table with her arms around him. She captioned the post:
“Special shout out to my favorite ex @50cent (and the only ex-boyfriend I am still asked about in every interview) who gets an extra special shout out in my @hbomax special. Now, everyone will know that you’re one big fat teddybear. Xx.”
Chelsea Handler Recalls 50 Cent ‘Convincing’ Her To Date Him, Reveals ‘Biggest Disappointment’ While Dating
15 years later, Chelsea Handler recalls dating Jamaica, Queens, New York rapper 50 Cent, telling Scott Evans:
“He convinced me to date him after he was on my show [Chelsea Lately]. 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. And my assistant was like, ‘Curtis Cent has called three times.’ And I was like, ‘Who’s Curtis Cent?’ She’s like, ‘Fitty.’ I’m like, ‘Oh, really? Now it’s ‘Fitty?” Two white girls. I’m like, ‘We went from Curtis to ‘Fitty?””
As Evans continues uncontrollably laughing, Handler continues with her story. She said:
“So, I was like, ‘Oh.’ And she goes, ‘He wants to call you.’ I go, ‘Oh, I don’t want to talk to him.’ He’s like, you know, all those guys used to hit on me. But, it was just kind of like play But, Curtis was sweet. He was sweet. ‘Cause he seemed gangster, but he wasn’t a gangster. 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.’ So, then I was like, ‘Listen, I’m not going out with you. I have a show in New Orleans this weekend, you’re welcome to come. You can meet me in New Orleans. This is my hotel. You’re welcome to get a room and you can come to my show. And you know, we’ll go and have a drink.'”
Handler went on to recall one of their first meetups, which happened in New Orleans.
“I go, ‘Do you want to go for a walk?’ And he goes, ‘I can’t really go for a walk outside.’ And I was like, ‘Who do you think you are?’ He’s like, ‘I can’t go for a walk outside.’ And I was like, ‘I think you can.’ Like, get over yourself. So, we go for a walk. And it was crazy. Like, every person we saw was like, ’50 Cent!’ I was like, ‘Oh sh*t.’ I didn’t get it. I didn’t know. We’re in New Orleans and it’s Black people, and everyone knew him. And he’s like a major deal.”
Chelsea Handler then revealed one of the ‘biggest disappointments” with dating 50 Cent. She admitted:
“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. I was like, ‘You don’t drink or do drugs?’ 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.”
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