(Handler and the rapper dated for two months in 2011.)
“Meanwhile, I realized he was borrowing all these cars from different dealerships.
I was like, ‘you’ve got the option to do that?’

Chelsea Handler and 50 Cent.Credit:Jamie McCarthy/Getty;Theo Wargo/Getty
I’m like, ‘Oh.'”
Gotham/GC
The relationship may have been short-lived but Handler got more than just a good story out of it.
“Then I got a Bentley.

Chelsea Handler at the 2024 US Open Tennis Championships.Gotham/GC
“I love 50 Cent, he was fun.
He was just a sweetheart and he was fun to be around,“she toldEntertainment Tonightin January 2023.
“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.
But yeah, I mean, if I saw him Id definitely have a drink with him.”