Chelsea Handler Shares the Sweet Story Behind Dating 50 Cent
So, Chelsea Handler has opened up once again about her brief but unforgettable romance with 50 Cent, and the way she tells it, the whole thing started in the most unexpected — and charming — way. While chatting on Scott Evans’ “House Guest” podcast, she explained that 50 Cent basically convinced her to date him right after he appeared on her show. It was a Friday taping, nothing out of the ordinary, and then she walked into her office over the weekend to find dozens and dozens of roses waiting for her. Her assistant then informed her that “Curtis Cent” had called three times — and Chelsea, not realizing “Curtis” meant 50 Cent, just asked who on earth that was.
Once she figured it out, she still wasn’t exactly jumping at the chance to talk. She joked that plenty of guys in the industry hit on her back then, so she brushed it off at first. But she also admitted that what stood out about 50 Cent was how genuinely sweet he was. She even laughed about how surprising that sweetness felt, considering his reputation and the fact that he had survived being shot multiple times. It didn’t match the tough image she had in her head.
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Even after telling him she wasn’t going to go out with him, she still invited him to one of her comedy shows in New Orleans and suggested they could grab a drink afterward. That simple plan eventually led to their short-lived but widely talked-about relationship back in 2011. She now looks back on him as “one of the sweetest people,” and says her friends absolutely loved having him around.
Chelsea also retold one of the funniest parts of that time in her life — how 50 Cent would show up every night in a different luxury car, from a Lamborghini to a yellow Ferrari. At first she thought he owned them all, until she realized he was borrowing them from dealerships. She joked about not knowing celebrities could do that, and in response, she bought her own “chocolate Bentley” as a playful gesture. Then the relationship ended, and she was left driving that Bentley for two years, laughing at the whole situation in hindsight.
Even now, she calls him her “favorite ex,” saying he was fun, thoughtful, and loved by everyone around her. And although the romance only lasted two months, she insists she’d happily grab a drink with him today if their paths crossed again.
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