NEWSKelly Osbourne Raved Over Meeting 'Gentleman' Sean 'Diddy' Combs Years Before His Trafficking Trial: 'He's So Put Together'
On an old episode of 'The Osbournes,' Kelly Osbourne said disgraced star Sean 'Diddy' Combs was 'such a gentleman' when she met him.
Sept. 8 2025, Published 11:56 a.m. ET
Before Sean "Diddy" Combs' reputation and career went south due to his s-- trafficking trial, Sharon Osbourne lusted over the idea of the rapper dating her daughter Kelly Osbourne.
In a resurfaced clip from MTV's reality show The Osbournes, the matriarch, 72, was giddy when she learned Kelly and Diddy were going to the same party.
Sharon and Kelly Osbourne Praise Sean 'Diddy' Combs
Before Sean 'Diddy' Combs' scandal, Sharon Osobroune wanted daughter Kelly to date the rapper.
"Wouldn't it be cool if Kelly went out with Puff Daddy? And I was Puff Daddy's mother-in-law? Puff Mummy," she quipped. "I think they would be so cute together."
Later in the episode, Kelly, 40, came home from the bash and revealed Sean, 55, gifted her a pricey watch. "Mum, he's so manicured, he's such a gentleman, he's so well put together," the Fashion Police alum raved.
Kelly Osbourne called Sean 'Diddy' Combs 'such a gentleman' when they met years ago.
"I bet he's got a nice old willy and all!" Sharon shockingly declared. "I bet it's smooth. I bet it's oiled. I bet it's just perfect."
"Stop, it's making me sick," Kelly shot back at her mom's NSFW remarks.
Kelly and Diddy never wound up dating.
Inside Sean 'Diddy' Combs' Scandal
- 'H--- No!': Usher Reveals He'd Never Let His Children Live With Sean 'Diddy' Combs in Resurfaced 2016 Interview
- Everything to Know About Aubrey O'Day and Sean 'Diddy' Combs' Relationship Amid the Embattled Music Mogul's Trial
- 'Tensions Are Skyrocketing': Sean 'Diddy' Combs' Family Feuding Over Disgraced Rapper's $400 Million Empire
Want OK! each day? Sign up here!
Sean 'Diddy' Combs has been in jail since September 2024.
While Sean was a huge star in his heyday, he suffered a fall from grace when he was arrested in September 2024 on s-- trafficking allegations. On July 2, after a messy trial, he was found not guilty on charges of trafficking and racketeering conspiracy, but was found guilty of transportation to engage in prostitution.
He's still behind bars, as judge Arun Subramanian denied his bail requests several times, noting the music mogul's lawyers failed to prove he wasn't a "danger to any person," as there was an act of violence toward a woman in June 2024.
The rapper was found guilty of transportation to engage in prostitution but escaped trafficking and racketeering charges.
In a filing, the judge ruled the court must "find by clear and convincing evidence that the person is not likely to flee or pose a danger to the safety of any other person or the community if released" — however, Combs poses a risk of "flight or danger."
His sentencing is set for October 3.
The Rapper Abused Ex Cassie Ventura
Sean 'Diddy' Combs was caught abusing ex Cassie Ventura.
Despite getting off on the most serious charges, Sean still faces dozens of sexual assault lawsuits from both men and women. Several of them claimed they were drugged and raped at one of his sexual parties, which he referred to as "freak offs."
His ex Cassie Ventura testified that she willingly participated in the gatherings, as she wanted to please her then-boyfriend and feared how he could react if she said no, as he was physically abusive toward her.
The mother-of-three, 39, was one of the people who asked the judge not to let her ex out on bail, as she believes he's likely "to pose a danger to the victims who testified in this case, including herself, as well as to the community."
