"It's a big pill to swallow in the beginning, but when you warm up to the idea, and you pick the right candidate, right?" Handler said of anal sex. "Small or medium, you know, you're not going to, like, do that with 50 Cent."
"Yo she is so crazy 😆😆😆," 50 responded, calling Handler "hand[s] down the funniest."
Handler and 50 Cent briefly dated over a decade ago.
The comedian spoke with Keshia Chanté for ET Canada earlier this year about a 2020 Instagram post where she referred to the mogul as her "favorite ex."
"Yeah, I guess he’s my favorite ex. I mean, I don’t have a favorite ex. I love 50 Cent, he was fun," Handler said. "He was just a sweetheart and he was fun to be around. My friends loved hanging out with him. I loved hanging out with him. It was a pretty short-lived romance, it was only two months."
Handler called out 50 Cent in 2020 after he seemingly endorsed Donald Trump for president on Twitter over alleged state tax increases proposed by Joe Biden. The comedian not only offered to pay Fif's taxes in order to change his mind, but declared he was no longer her favorite ex.
Handler later shared that she spoke privately with 50 Cent about his public support of Trump, revealing he was allegedly joking and vowed to be in Biden's corner.