![Sean Diddy Combs performing in a black outfit at VMA'S 'Club Love'.](https://www.cheatsheet.com/wp-content/uploads/2025/02/Sean-Diddy-Combs-Chelsea-Handler.webp)
Sean ‘Diddy’ Combs Chased Down Chelsea Handler Until Someone Had to Rescue Her
Sean ‘Diddy’ Combs’ past has been looked at in a new light ever since Cassie filed the first lawsuit against him. His infamous parties with celebrities have especially been reevaluated with intense scrutiny thanks to his allegations. One celebrity, Chelsea Handler, experienced firsthand how persistent Diddy could be when he saw someone he wanted at these parties.
Chelsea Handler told Sean ‘Diddy’ Combs he ‘looked like a rapist’ when they partied
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Diddy and Handler got to know each other when the music mogul stopped by to chat with her on her old talk show Chelsea Lately. One of the most famous parts of the interview was Diddy immediately trying to charm Handler the moment he arrived on set.
“Chelsea, I have been waiting to get here. I’m talking about, man, it feels so good to see you face to face,” he told her.
But Diddy already rubbed Handler the wrong way when he showed up an hour late to the episode. And Handler was quick to call out Diddy for his punctuality.
“It’s interesting that you’ve been waiting to get here, because I’ve been waiting for you for a f***ing hour,” she told him.
Handler would continue to throw barbs at Diddy during the interview, although Diddy spent a good chunk of the segment trying to woo her. Eventually, Diddy joked that he’d expose himself to Handler after Handler called him a girl.
“The girl thing, I’m not really feeling that,” Diddy said. “I will pull out my schlong right here, right now.”
Although Handler and Diddy seemed to share a lot of chemistry, Handler’s opinion on Diddy might’ve lowered when she attended one of his parties. In an interview on The Howard Stern Show (via Classicalite), Handler was very candid about her feelings towards certain celebrities. Stars like baseball player Alex Rodriguez was one of many that got on the comedian’s bad side.
“I just find him gross,” she said about Rodriguez. “The way he conducts himself. He has a centaur of himself in his house, yeah, him and a horse COMBINED into one person. We’ve shown it on the show…He just sleeps around…He is a pile of s***.”
But talking about Rodriguez only reminded Handler of Diddy. The comedian was yet another person who described an uncomfortable and perhaps scary encounter with the music mogul.
“The same thing with P.Diddy. He was chasing me around at that party last year. He saw me around this bush and he said, ‘Oh, I’m gonna get you.’ I go, ‘No you’re not. You’re never gonna get me. Get away from me, you’re never going to get anything.’ He was literally chasing me around a bush. I was like, ‘Look at you. You look like a rapist right now, chasing a woman around a bush at a party.’ And someone came and rescued me,” she said.
Chelsea Handler considers her old boyfriend 50 Cent an ally against Sean ‘Diddy’ Combs
Whereas Handler’s opinion on Diddy only got worse, her opinion on 50 Cent might’ve only gotten higher. Handler and 50 Cent briefly dated in 2011 after she met the “In Da Club” artist on her show. Incidentally, 50 Cent has been one of Diddy’s most outspoken critics for decades. On an Instagram video, Handler revealed that she was well-aware of Diddy’s rivalry with her ex-boyfriend. Handler seemed proud of the way the rapper was continuing his crusade against his longtime nemesis.
“My ex-boo, Curtis ’50 Cent’ Jackson, is in the news, and not surprisingly, to me at least, he’s an ally,” Handler said. “As you probably heard, Diddy is in deep doo-doo, facing quite a slew of allegations. Well, Mr. Cent has come forward to say that he is not only going to produce a documentary about the allegations, he’s going to donate the proceeds to victims of sexual assault. Do I know how to pick a rapper or what?”
Handler also quipped that she still held a grudge against Diddy for showing up late to Chelsea Lately more than anything else.
“But like I always say, in a world full of Diddys, be a Fiddy. If, for no other reason, than Diddy was once more than a f***ing hour late to a taping of Chelsea Lately. And Fiddy always showed up to my Candy Shop on time,” she said.
How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area.