Handler and Fif previously dated, but called it quits following a convo between Handler and R&B star Ciara.

Jamie McCarthy/Getty Images; Frazer Harrison/Getty Images

50 Cent has shared his reaction to being mentioned in a seemingly flattering manner by Chelsea Handler as part of a comedy bit discussing anal sex.

On Sunday (May 21), Fif, who dated Handler over a decade ago, shared a clip of one of the multi-hyphenate’s stand-up comedy sets, in which she attempts to destigmatize anal sex by extolling its joys and pleasures.

“Anal sex is not just for homosexual men anymore, okay?” Handler says in the reel. “Ladies and gentlemen, it’s trending. And don’t knock it until you try it. You might f**king like it.” The Chelsea Lately host continued, subtly complimenting the size of 50’s “magic stick” by suggesting that someone interested in trying the sex act may not want to experiment with a man that’s well-endowed sexually. “It’s a big pill to swallow in the beginning but when you warm up to the idea, and you pick the right candidate, you know…small or medium, you’re not going to do that with, like, 50 Cent,” Handler joked. “You want to pick the right candidate.”

In the caption of the post, Fif appeared to enjoy Handler’s reference to him, as he praised the 48-year-old’s sense of humor. “Yo she is so crazy, @chelseahandler is hand down the funniest,” he wrote, adding an “LOL” and plugging his Branson Cognac and Le Chemin du Roi brands.

Rumors swirled around 50’s romance with Handler in the early ’10s, with a picture of the two kissing each other surfacing in 2012. Both parties ultimately confirmed that they dated, but that the fling was short-lived and ended due to unresolved feelings between 50 and his ex-girlfriend, R&B star Ciara.

The rapper opened up about his relationship with Handler in his 2020 book Hustle Harder, Harder Smarter, revealing he met Handler while appearing on her show and immediately began pursuing her. Despite admitting that the pair were an “odd couple” on the surface, he says it was Handler’s ambition and independence that caught his attention.

Chelsea Handler attends The Hollywood Reporter’s Women In Entertainment Gala presented by Lifetime on December 07, 2022 in Los Angeles, California. Jon Kopaloff/Getty Images

“What really attracted me to her was how she moved professionally,” Fif said of Handler in his book. “In addition to her talk show, she also had a reality show and was best-selling books. She was a real boss. With all of her various hustles, she was probably pulling in over $30 million a year.

That was sexy as **** to me. Most important, she made it very clear she didn’t need anything from me. Chelsea had way too much going on to ever look to me for making something happen for her. If anything, I was probably trying to soak up a little bit of her energy. Ultimately, it never went anywhere serious. There was a bit of a miscommunication before my ex-girlfriend Ciara was scheduled to appear on Chelsea’s TV show and we stopped talking after that.”

Despite the end of their romance, the two appear to have remained cordial, as they have both spoken glowingly about one another publicly on numerous occasions.