Jack Osbourne reveals Kelly’s awkward first encounter with Sean Diddy

Jack Osbourne has opened up about his sister Kelly Osbourne’s past encounter with Sean “Diddy” Combs, after their mother once urged her to date the disgraced rapper.

During an exclusive interview with Michael Rosenbaum on the Inside of You podcast, the 39-year-old shared details about the first time his sister met Diddy.

He recalled, “Kelly got invited to a Diddy party when she was about 18, and he ran into Kelly. Some weird thing happened where his bouncer knocked her over, and then he invited her to one of his parties.

“I think she ended up winning that. He gave her some diamonds, brought her to a party, and she went, ‘Later’.”

This comes after a video resurfaced online of Sharon Osbourne expressing her wish for her daughter to date Diddy.

In an episode of the reality TV series The Osbournes, Sharon joked that she would like to be P. Diddy’s mother-in-law.

For the unversed, Diddy is currently behind bars on charges of sex trafficking and racketeering while awaiting sentencing for the transportation of prostitutes.