Kelly Osbourne Has Had A Chaotic Relationship History

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As the daughter of rock legend Ozzy Osbourne, Kelly Osbourne's major transformation has been largely chronicled in the spotlight, with her romances making plenty of headlines along the way. The London native broke things off with her longtime partner Sid Wilson, known as the DJ for Slipknot, in March 2026. The two originally went public with their romance in January 2022, going on to welcome a son in November 2022 and becoming engaged in July 2025. 

While experts have weighed in on the best age gap for a successful relationship, the disparity between the duo is enough to turn heads on its own. The Slipknot figure is seven years Osbourne's senior, with their social media hard launch coming on his 45th birthday, but they originally met when he was in his 20s and the TV personality was just 13 years old. The former "Fashion Police" star spoke on "The Osbournes" podcast about how they reconnected in 2013, adding that things really changed after he invited her to a SoFi performance shortly before COVID-19.

"I went to the show, still had no idea that he liked me, and then we just started talking more and hanging out more, and it happened really naturally," Osbourne said. "Because we had been friends for so long and known each other for so long, there was a sense of comfortability that I've never had with anyone else."  While the split marks a major change for Kelly Osbourne, it's only one piece of her relationship history. 

Kelly Osbourne's relationship with Sid Wilson isn't the only one that's featured a questionable age gap detail. While all the timeline specifics aren't known, she became involved with The Used frontman Bert McCracken back in the early 2000s. The two reportedly met at Ozzfest, the heavy metal music festival founded by Sharon and Ozzy Osbourne, in the summer of 2002, when Osbourne was 17 and McCracken was 20.

Their budding romance was witnessed on "The Osbournes," the rock family's hit reality TV show, and was the subject of the episode "Beauty and the Bert." Osbourne avoided introducing the musician to her family throughout the installment, with his eventual introduction to her mom Sharon resulting in major embarrassment for the young Osbourne. Their relationship later unraveled in the Season 2 finale, culminating in McCracken breaking things off over the phone on Valentine's Day. "His excuse was just disgusting," Osbourne said in the episode. "He goes, 'People don't take me seriously because I date you.'"

Meanwhile, McCracken weighed in on the breakup during an interview with Playboy. "I did it over the phone. I'm such a d***head," he said, per Blabber Mouth. While Kelly Osbourne pointed to an oversized ego as the reason for their split, The Used star provided a different reason. "I'm just not ready for a relationship, period, let alone a huge, public relationship," he continued. "I just hope that someday I can maybe be with someone as good and perfect as she is."

Following her televised relationship with Bert McCracken, Kelly Osbourne had a few more relationships throughout the early 2000s. Though it was never confirmed, she was rumored to have linked up with Kevin Zegers in mid-2006. The actor starred in "It's a Boy Girl Thing," a teen comedy that marked Sharon Osbourne's acting debut, and was pictured with Kelly at events like the annual White Tie and Tiara Ball to Benefit the Elton John AIDS Foundation.

The reality TV star was then connected to musician Matty Derham in late 2006, with the pair even sparking wedding rumors after attending an Irish festival together. "Over the weekend a number of rumours circulated very quickly suggesting that Kelly Osbourne had got married at a festival in Ireland," Osbourne's rep Gary Farrow told the Irish Examiner. "This is totally untrue and is as real as the inflatable church that carries out these non-legally binding mock marriages for fun."

Kelly Osbourne was then linked to McFly star Danny Jones in 2008, but the short-lived connection may have been killed by Ozzy Osbourne. Jones shared with The Mirror that he spent an entire night talking to Osbourne after meeting at a club, only to have their conversation interrupted by her rock legend dad in his underwear. "He sat next to me at the kitchen table, wolfed down a couple of buns and grumbled: 'Who are you, then?'" Jones recounted. "I left soon after he returned to bed, even though Kelly asked me to stay ... Weirdly, Kelly never contacted me again."

Kelly Osbourne's relationship with Luke Worrall marks quite the chaotic chapter in the celeb's love life. The model was questionably young for "The View" host at the time, as they began dating in 2008 when he was 18 and she was 23. Regardless, they made headlines when he changed his relationship status to "engaged to Kelly Osbourne" on Facebook in November that year. Kelly spoke highly of her beau in the media during this time, even slapping a reporter who insulted him, until constant rumors of Worrall's infidelity turned things sour.

The duo initially called off their engagement in July 2010. Though they seemingly tried to amend things later in the year, their relationship was dealt the final blow when the model's continued cheating was exposed in December, prompting Osbourne to go on a Twitter rant about the situation. "I am and always will be 2 good 4 @ luke_worrall darling ur pretty face will only get you so far because u don't have the brains to back it up," she wrote, per Today.

Additionally, the media sensationalized the fact that Worrall cheated with a transgender model named Elle Schneider, with Osbourne's transphobic comments only fueling the campaign. Despite previously positioning herself as an LGBTQIA+ advocate, she used a transphobic slur and made insensitive comments in an interview with Glamour UK. "Up until then, I'd always thought that the worst way to get cheated on would be with an ugly girl," she said, per TransAdvocate. Osbourne has since apologized for her comments, but it marked a messy end to her relationship with Worrall, either way.

Kelly Osbourne was linked to motocross racer Josh Hansen in August 2010 amidst her initial split from Luke Worrall. The two reportedly spent time together during Ozzfest before being pictured leaving a Hollywood restaurant together. The celeb also fueled public speculation by shouting out her potential beau on Twitter (Now X). "Please follow @joshhansen100 if he does not get 10,000 followers buy [sic] the end of the day he is going 2 get Sid for a day this can't happen," she wrote, referring to her dog.

Osbourne wasn't the only one on the rebound, though, as Hansen had recently split from reality TV star Stephanie Pratt. The star of "The Hills" shared her side of the story in her memoir "Made in Reality," alleging some shifty behavior on the part of Osbourne. In the 2015 release, Pratt recalled being comforted by the "Fashion Police" host at a party, quoting her as saying, "I'm so sorry. Josh is the worst, such a total d***head. Sleep on it tonight — just keep hanging out with us, you can do so much better, forget about him."

Osbourne's camaraderie was seemingly short-lived, though. "One week later — one! — I look at Perez Hilton's website and see an article about Kelly Osbourne and Josh Hansen on a date," Pratt wrote. While Osbourne's relationship with Hansen seemingly fizzled out pretty quickly, the brief fling wasn't without its own share of drama.

From there, Kelly Osbourne had another serious relationship with chef Matthew Mosshart. The two met in July 2011 at the wedding of supermodel Kate Moss and The Kills guitarist Jamie Hince, with the budding romance going public in December 2011 when they were pictured together in New York City. When the duo announced their engagement in July 2013, Osbourne shared that Mosshart had also made a cross-country move for her.

"Matthew made the biggest sacrifice anyone's ever made for me, to move away from everything that he knew to be with me in LA," she told Hello! Magazine. "Long-distance relationships often don't work out. We'd dated for a year and knew we wanted to be together." The two were consistently photographed looking head-over-heels in love throughout 2012 and 2013, attending events like the Costume Institute Gala and New York Fashion Week together.

Still, Osbourne and Mosshart ultimately went their separate ways in 2014, with "The Osbournes" star speaking about the split to E! News. "It was a mutual decision," she explained. "We love each other very much. It just wasn't the right time for us, and I think if we weren't as mature and adult than we are, then we could have gone down a road that wasn't really nice." She added that they remain great friends, with the relationship's end avoiding the drama of some of her other notable romances.

Before finding stability with Sid Wilson in 2022, Kelly Osbourne had another smattering of rumored romances throughout the 2010s. In June 2014, Us Weekly reported that the "Dancing with the Stars" contestant was having fun with actor and singer Quincy Brown, but was also interested in spending time with British model Ricki Hall. "Kelly is single, but she's having a lot of fun. She's been hooking up with Quincy, her really good friend lately," a source told the outlet. About Hall, they added, "She's definitely interested in seeing where it goes with him."

Throughout 2016, Osbourne was linked to country star Dustin Lynch and creative director Kes Glozier, with the latter relationship initially looking like it was getting serious. "They want to do things the right way and are taking it slow, getting to know each other," an insider told Us Weekly. "They are going on dates and talking a lot." Still, things appeared to eventually fizzle out between the two Brits.

Osbourne then dated model Jimmy Q in 2019. The two made some notable appearances together, but ultimately went their separate ways after four months of dating. "Kelly and Jimmy initially seemed really well suited and were incredibly smitten," said a source, per The Daily Mail. "It just made sense for them to go their separate ways as they wanted different things." For more content about the reality TV star, check out Kelly Osbourne's drastic transformation, as highlighted with side-by-side pics.