Are Kelly Osbourne, Sid Wilson Together Again? Here's Why Their Engagement 'Ended In Pain'

Kelly Osbourne has said her engagement to Slipknot DJ Sid Wilson 'ended in pain', but the TV personality insisted she still has 'hope for real love' as she stepped out at a friend's wedding in the weeks after their split was revealed.

The 41‑year‑old TV personality is reported to have split from Wilson last month, seven months after he proposed. The pair, who had been together for more than three years, share a son, Sidney, born in November 2022, and were widely seen as settling into family life before the engagement was quietly called off, according to accounts given to the Mail.

'Hope For Real Love' After Sid Wilson Split

Despite the recent upheaval, Kelly Osbourne has been unexpectedly candid about how she feels now. This week she attended the wedding of actor Bradley Riches, a friend she made after her mother Sharon Osbourne appeared alongside him on Celebrity Big Brother.

In a clip from the celebration, later posted on Riches' Instagram, Kelly appears visibly moved as she talks straight to the camera about the ceremony she has just watched. 'It's so real. Like, real love!' she says. 'It gave me hope because I'm like, It's still out there!'

The moment was brief, but it carried weight. After a broken engagement and a year marked by personal loss, Osbourne was not presenting herself as untouched by any of it, only as someone still willing to say love remains possible.

Away from the wedding, her social media activity has added to the sense that she is edging into a new phase of her life. Kelly has recently begun spotlighting Los Angeles‑based barber and creative Kiinicki, 37, the founder of Hella Good Hair, who uses they/them pronouns.

She has shared photos of Kiinicki on Instagram, then reposted a close‑up selfie of them with a thinking‑face emoji. In another story, she uploaded a candid shot of them at an event and joked: 'buy one, get one @leandraearl' with a winking emoji.

According to the Mail, Kelly and Kiinicki were seen 'all over each other' at an exclusive after‑party for Lily Allen's London Palladium shows at the Broadwick Hotel in Soho, laughing together in a tucked‑away corner among the hotel's sofas, and the same outlet has also reported that they now share matching crescent‑moon‑and‑tooth tattoos said to have been done in the US during the same month Osbourne was last seen publicly with Wilson at the Grammys.

None of this has been confirmed by Osbourne or Kiinicki, and Kelly has not explained the tattoos or their timing, so any link between these details and the end of her engagement remains unverified.

Kelly Osbourne, Sid Wilson And A Relationship Under Strain

Behind the current speculation sits a relationship that, on paper, looked like rock‑royalty symmetry. Kelly Osbourne and Sid Wilson's romance grew out of the world both came from. The Slipknot musician is said to have proposed backstage at what was billed as Ozzy Osbourne's final Black Sabbath gig, in a quiet moment witnessed by Kelly's parents.

For a while, it appeared to be a straightforward story: the daughter of a metal legend building a family with another musician, a baby son arriving, an engagement in place. But sources quoted by the Mail suggested the reality was more fragile than the public image.

'In truth, she and Sid have been facing challenges in their relationship for some time, and things were not as they appeared,' one source told the Mail. The same report said that, although the couple tried to persevere for the sake of their child, they eventually decided to end the engagement.

The pressure of grief sat heavily alongside those tensions. Kelly's father, Ozzy Osbourne, died on 22 July 2025 after years of health issues, including Parkinson's disease. Those close to her told the Mail that losing him had been a major strain.

'Kelly has been struggling following the loss of her father,' one insider said. 'The grieving process has been incredibly difficult, and she's been doing everything she can to cope. They tried to make it work, particularly for the sake of their child, but ultimately decided that separating is the best path forward.'

Kelly has not publicly detailed what led to the split with Wilson. She has, however, made clear how heavily the past year has weighed on her, telling followers, 'I am ill right now.'

Around the time their split became public, she also shared a cryptic Instagram reel referencing 'abuse' on her stories. She did not add commentary, did not name Wilson and has not, in any subsequent statement, tied that post to him or to their relationship. With no direct confirmation from Kelly, any connection between the reel and her former fiancé remains unproven and should be treated cautiously.

Sid Wilson has not publicly commented on the breakup or on Osbourne's recent posts. There is nothing in the available reporting to suggest a reunion is on the cards. What remains is a relationship that did not survive grief and pressure, and a Kelly Osbourne still insisting, with surprising bluntness, that real love is out there.