Chelsea Handler Praises Ex-Boyfriend 50 Cent for His 'Relentless' Trolling of Sean 'Diddy' Combs, Jokes She 'Should Probably Revisit' Relationship

Chelsea Handler applauded her former boyfriend for trolling Sean "Diddy" Combs amid the music mogul's fall from grace.

Combs, 56, was convicted on two prostitution-related charges in July 2025, though he was acquitted of racketeering and s-- trafficking. "50 Cent" (born Curtis Jackson III) executive-produced a Netflix documentary about the former rapper's crimes that debuted in December 2025.

During a recent appearance on the "We Might Be Drunk Podcast" podcast, Handler, 50, declared, "I love what Fiddy’s doing to Diddy."

"He’s relentless," the comedian noted," adding, "Fiddy’s great…. I should probably revisit that. People [would] like that a lot."

"H--- yeah!" co-host Mark Normand replied, to which she quipped, "That made a lot of people happy."

Handler went on to boast about being "the only" ex of the "In Da Club" hitmaker that he doesn't "talk s--- about."

"Someone was saying he talks s--- on all his exes, and I'm one of the only ones he talks about respectfully," she said.

Handler "casually dated" the G-Unit rapper, also 50, back in the early 2010s. Revealing how the fling began in another recent interview, she shared that he sent her flowers following a guest appearance on her E! talk show Chelsea Lately.

The stand-up also said that while the relationship only lasted "a very short time," she felt that it "blew up" in part because people didn't know what to make of their pairing.

"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," she recalled.

The My Horizontal Life author has a new man, though, whom she unexpectedly met a blackjack table in Las Vegas in late November 2025.

Recounting the "cute story" to Andy Cohen during an appearance on his radio show on Monday, January 12, Handler shared how she sat next to a guy with "big cowboy hat on" and asked him "to borrow a couple thousand chips."

After he obliged, she won enough money to pay him back, and the pair hit it off.

"I get all these texts from this guy the next day," she spilled. "And he's like, 'That was such a vibe. You're so fun. I want to hang out again.'"

Handler dished, "He goes, 'You seem like a great adventure, and I'm in the mood for some adventure in my life.'"

The This Means War actress subsequently invited him on a nine-day cruise to Antarctica she was about to take, and he showed up.