Jack Osbourne recently shared an amusing memory on the Inside of You podcast hosted by Michael Rosenbaum, where he recalled his sister Kelly Osbourne’s unusual first encounter with music mogul Sean “Diddy” Combs.
Kelly, then just 18 years old, had been invited to one of Diddy’s parties. However, their first meeting didn’t exactly go as planned. According to Jack, Kelly was accidentally knocked over by one of Diddy’s bouncers. Despite the awkward start, Diddy extended an invitation to his event, which turned the situation around. Jack jokingly added that Diddy even gifted Kelly some diamonds and invited her to a glamorous party.
The story resurfaced around the same time a throwback clip circulated from The Osbournes reality show, where Sharon Osbourne humorously suggested it would be “cool” if Kelly dated Diddy, joking about becoming his mother-in-law.
Adding context to the story, Sean “Diddy” Combs is currently embroiled in legal troubles, facing charges connected to sex trafficking and racketeering. While he was acquitted of racketeering conspiracy and some sex trafficking allegations, the ongoing case has placed him at the center of public scrutiny.
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