Comedian, actress, and host Chelsea Handler is spilling the tea on her past romance with rapper 50 Cent. She’s dishing on how he “convinced” her to date him a decade and a half ago, and what ultimately turned out to be the “biggest disappointment” in their relationship.
During a recent chat on Scott Evans’ ‘House Guest’ podcast, Handler, now 50, took fans back to a time when her romantic link to 50 Cent (real name Curtis Jackson) sent shockwaves. Their story began in 2009, right after the Queens rapper graced her show, ‘Chelsea Lately,’ on E!
The couple parted ways in 2010, but they’ve kept things cool and positive ever since. In fact, back in August 2020, Handler gave a shoutout to her “favorite ex” on Instagram. She shared a photo of them at a dinner table, her arms around him, with a sweet caption:
“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
Fast forward 15 years, Chelsea Handler is reminiscing about her time dating the Jamaica, Queens, New York rapper, telling Scott Evans how it all went down:
“He totally won me over after appearing on my show, ‘Chelsea Lately,’” she explained. “It was a Friday, he was a guest. Then, over the weekend, my office was flooded with dozens of roses. My assistant was like, ‘Curtis Cent has called three times.’ I was confused, ‘Who’s Curtis Cent?’ She corrected me, ‘Fitty.’ I was like, ‘Oh, really? Now it’s ‘Fitty’?” She chuckled, adding, “Just two white girls, like, ‘We went from Curtis to ‘Fitty’?’”
As Evans couldn’t stop laughing, Handler pressed on with the story:
“So, I thought, ‘Okay.’ My assistant said, ‘He wants to call you.’ I was hesitant, ‘Oh, I don’t want to talk to him.’ You know, back then, lots of guys would hit on me, but it was usually just playful. But Curtis, he was genuinely sweet. He had that gangster persona, but he wasn’t really a gangster. I mean, the fact he was shot so many times, you just think, ‘How did you get shot? It just doesn’t track.’ So, I told him, ‘Look, I’m not going on a date with you. I have a show in New Orleans this weekend. You’re welcome to come. You can meet me there, at my hotel. Feel free to get a room, come to my show, and we can grab a drink.’”
Handler then recalled one of their early meetups, right there in the Big Easy.
“I asked him, ‘Do you want to go for a walk?’ And he responded, ‘I can’t really go for a walk outside.’ My reaction was, ‘Who do you think you are?’ He repeated, ‘I can’t go for a walk outside.’ I pushed back, ‘I think you can. Seriously, get over yourself.’ So, we went for that walk. And it was wild! Everywhere we went, people were shouting, ’50 Cent!’ I was like, ‘Oh, sh*t.’ I really didn’t grasp it. I didn’t realize. We were in New Orleans, among Black people, and everyone knew him. He was a major, major deal.”
Then, Chelsea Handler dropped the bombshell about one of her ‘biggest disappointments’ during her time with 50 Cent. She confessed:
“He actually came to my show. He was incredibly sweet, just such a sweet guy. And the biggest letdown? He doesn’t do drugs. I was like, ‘Wait, you don’t drink or do drugs?’ We only dated for a short time, but people went crazy over us. Everyone was asking, ‘What are these two doing together?’ But honestly, he was truly one of the sweetest people I’ve ever met.”
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