Kelly Osbourne Sparks New Romance Rumors With Cozy Pics After Failed Engagement

Kelly Osbourne appears to be moving on only two weeks after reports that she had called off her brief engagement to Slipknot DJ Sid Wilson surfaced. Kelly and Wilson share a son, Sidney, born in late 2022. The couple hard-launched their relationship on Instagram earlier that year. Wilson proposed to the former "Fashion Police" judge in July 2025, at her late father Ozzy Osbourne's final show with his band, Black Sabbath. The rock legend died just weeks after witnessing his daughter's magical moment, on July 22. Wilson and Kelly's relationship had reportedly been strained while she navigates her grief, but her April 2026 Instagram post is another red flag in a relationship that was full of them, so maybe they just aren't meant to be. 

On Easter Sunday — April 5, 2026 — the former pop singer posted cozy photos enjoying the holiday with Sidney and tattoo artist Miles Langford. The pair had huge smiles on as they posed with Kelly's son between them for their tea time at The Dorchester Hotel in London. There were also photos of Langford holding Sidney, sometimes with a dog between them. "Had a fantastic time catching up with uncle @mileslangford having afternoon tea @thedorchester," Kelly wrote in the caption. "Baby Sidney had the best time ever!" 

kellyosbourne/Instagram

But people in the comments weren't buying that the outing was platonic. "You already moved on? That quick?" someone said. "Is she ever going to let see Syd his dad? He needs his dad too," another person wrote. "Sid will get mad see this pic got new man not good idea," someone warned. 

Kelly Osbourne has understandably been struggling since Ozzy Osbourne's death in July 2025. Many of her decisions in the aftermath of losing her father have been questionable. In fact, she and Sid Wilson started raising eyebrows with the odd timing of her engagement. It's not Kelly's fault but some people online questioned why Wilson would propose to her on a night that was already emotionally charged. 

Then, after Ozzy died, Kelly's difficult year got even worse, as she lost an alarming amount of weight that had friends and fans worried about her health. Per the Daily Mail report on their breakup, Kelly and Wilson had been having problems for months before tragedy struck the Osbourne family. The former couple attended the 2026 Grammys together in February, but hadn't been seen together in public since. So, it's possible they broke up well before reports were published, making Kelly's reported new romance slightly more acceptable. 

Kelly, Sidney, and Miles Langford had plenty of support in the comments, too. Plus, there was also speculation that she was seeing Kiinicki as recently as April 3. So, people online should try not to put labels on her relationships before she does. She looks happier and healthier with Langford and Sidney than she has in the recent past — that's all that matters.