10 Photos of Kelly Osbourne and Sid Wilson Before Their Shocking Split: Did Someone Cheat?

Kelly Osbourne has quietly ended her engagement to Slipknot DJ Sid Wilson in Los Angeles, with the pair calling time on their relationship eight months after his backstage proposal at Ozzy Osbourne's final Black Sabbath concert, according to multiple reports published in late March.

The 40-year-old Osbourne, who shares son Sidney with Wilson and is still deep in grief over her father's death last summer, is now said to be relying heavily on a small circle of friends, including non-binary barber Kiinicki, as she navigates what insiders describe as an 'overwhelming' period.

From Ozzfest to Engagement

The news came after what, from the outside, appeared to be a rare moment of calm and happiness in Kelly Osbourne's often turbulent public life. Wilson, 49, was not a fleeting romance from the celebrity circuit but someone she had known for nearly three decades. They first met 27 years ago when Slipknot joined Ozzfest, the heavy metal touring festival created by Ozzy and Sharon Osbourne.

A backstage friendship slowly evolved into a relationship, and by July last year, Wilson was proposing in Birmingham, presenting Kelly with a large diamond ring in front of her entire family at what would turn out to be Ozzy's final Black Sabbath show.

That proposal now sits uncomfortably close to another life-changing moment. Ozzy Osbourne died just weeks later, on 25 July 2025, aged 76, after a heart attack. He had lived for years with Parkinson's disease and coronary artery disease, but the timing of his death nonetheless stunned the family.

Kelly has repeatedly described her father as her 'best friend,' and reporting in the Daily Mail and People has underlined how central that relationship was to her day-to-day sense of stability.

Kelly Osbourne's Grief and a Relationship Under Pressure

It is within that compressed window of public celebration and private loss that the relationship between Kelly Osbourne and Wilson appears to have come under strain. Sources quoted by the Mail say the couple had been dealing with 'challenges for months' before the split surfaced publicly.

They reportedly tried to hold things together for the sake of their young son Sidney, but ultimately decided that calling off the engagement — at least for now — was the most practical option.

One insider suggested Ozzy's death 'fundamentally changed' Kelly's outlook, claiming her priorities shifted almost overnight. Those same reports point to the impact grief has had on her physically, with friends allegedly worried as she struggled to maintain her weight. Kelly Osbourne or her representatives have confirmed none of those health concerns, and there has been no official comment on her condition, so these claims remain unverified and should be treated with caution.

What is clearer is where her energy is now directed. Kelly Osbourne is said to be concentrating on motherhood and on supporting Sharon, with whom she has a close, if sometimes complicated, bond. The pair have been seen together at several recent events, most notably the BRIT Awards in March, where Sharon accepted a Lifetime Achievement Award on Ozzy's behalf.

That high-profile appearance also exposed another familiar fault line in Kelly's life. Her look on the night sparked a fresh round of commentary about her appearance, with online critics insisting she had 'drastically changed.' Kelly, who has previously spoken openly about addiction and body image, has reportedly chosen not to answer back this time, allowing the speculation to swirl without public rebuttal.

Kelly Osbourne, Kiinicki, and Rumours of a 'Third Party'

If Wilson has taken a step back from Kelly Osbourne's public orbit, another figure has moved sharply into focus. Non-binary barber Kiinicki, 37, has become a regular presence by her side in recent months. The two have been photographed together at multiple outings, including Lily Allen's West End Girl show afterparty at the Broadwick Soho Hotel, where a partygoer told the Mail they were 'all over each other all night' and made little effort to conceal their closeness.

In February, Kelly Osbourne and Kiinicki underlined their bond with matching tattoos, each getting a crescent moon and tooth inked on their hands. On Instagram, Kelly has posted playful clips of the pair looking after Sidney when he developed conjunctivitis, presenting a snapshot of a tight, improvised support unit gathered around a sick toddler.

Inevitably, those images have led to questions about whether this is simply an intense friendship or something edging into romance. Sources cited by HOLA! USA have pushed back at suggestions of scandal, insisting Kiinicki has been a 'source of support' during an especially heavy time rather than a wedge driven between Kelly and Wilson.

At this stage, there is no verified evidence that cheating played any part in the breakup, and multiple reports stress that no 'third party' was involved in the decision to end the engagement. Anything beyond that remains speculation and should be approached with scepticism.