Inside Kelly Osbourne's Relationship With Her Famous Exes

Reality TV star and rock royalty Kelly Osbourne has been involved with various men in various relationships throughout her adulthood and has even been engaged three times. While some of Osbourne's relationships played out relatively low-key and ultimately ended on amicable terms, the reality star has had to weather cheating scandals, explosive short-lived relationships that didn't end up going anywhere at all, and even instances where her family may have accidentally sabotaged a relationship — and the media documented most of these relationships in real-time.

Despite some lows, Osbourne — who also prides herself on being a successful actress, fashion designer, singer, and model — has seemingly been able to come out on the other side and is now celebrating some pretty major highs with her latest beau. Have a look at some of the men with whom Osbourne has been in a relationship and learn all about how things ended up for them.

Kelly Osbourne and musician Bert McCracken's relationship played out on television during the second season of Osbourne's family's show, "The Osbournes." The two certainly had a relationship that can best be described as on and off, and McCracken ultimately admitted to Playboy that he broke up with Osbourne in a pretty terrible way: over the phone. 

McCracken also said that, in the end, he wasn't ready to be in the type of relationship Osbourne wanted. But, as he told the publication, he was ultimately the problem. McCracken said, "She's the most important girlfriend I've ever had. We're best friends. It was always just so pleasant when she was around" (via Metro).

While speaking to MTV News in 2004, it was clear that despite those positive feelings, McCracken was also growing weary of being asked about his ex-girlfriend so often, especially as his band began to achieve success while the two were together. Despite that, in the end, it appears the two parted ways on friendly terms at the very least.

Kelly Osbourne and musician Danny Jones dated in 2008. While things seemed like they were going well for the two, it turns out that Osbourne's father Ozzy Osbourne might have had something to do with their ultimate demise. While speaking to The Mirror in 2008, Jones recalled a night in which he and Kelly had returned to her family's home in Buckinghamshire after a night out.

He said, "She invited me back to her parents' place to stay the night, so I went. We were sitting downstairs chatting and stuff until about 7 a.m. Then Ozzy Osbourne shuffled in wearing only these creased, black Y-fronts." Jones added that Ozzy made small awkward talk before leaving the room, and he opted to leave that night instead of staying over as Kelly wanted him to. He ended up never hearing from her again, adding, "I'm the kind of lad who likes to introduce myself to parents properly before I stay the night. It didn't feel right."

Following her breakup with Danny Jones, Kelly Osbourne entered into a two-year-long relationship with model Luke Worrall, who was five years her junior. Unfortunately, things between Osbourne and Worrall didn't end well, with Osbourne accusing Worrall of cheating on her at the end of the relationship, with both of them turning to social media to speak badly about each other.

As the Daily Mail reported, Osbourne first turned to Twitter to thank fans for supporting her. She wrote, "Thank you all so much for your support but the matter is private and will not be commenting enough damage has already be done." Eventually, she got dragged into discussions about what did or didn't happen with Worrall and ended her day by tweeting, "I have decided to comment through song and I believe En Vogue says it best," before linking to a video for the band's hit 1992 song "My Lovin' (You're Never Gonna Get It)."

A year after her breakup with Luke Worrall, Kelly Osbourne moved on to someone new. She moved in with her boyfriend and musician Rob Damiani this time. During the early days of their relationship, she said that she wanted privacy. She said, "It's true, I'm having fun getting to know someone new. I met Rob over in the U.K. recently, and I want to take things slowly, so that means keeping some things private" (via Digital Spy).

However, things with Daimaini weren't meant to be, and Osbourne soon found herself single again. In March 2011, Osbourne attended the Elton John Aids Foundation and seemed frustrated about her dating life and how the public perceived it. She admitted then, "I don't have a boyfriend right now. What's wrong with people? I stand next to a man and I'm with them. It's boring" (via The Mirror).

Kelly Osbourne announced her engagement to vegan chef Matthew Mosshart in January 2013, telling Hello! that she and her fiance were incredibly close — perhaps to a fault. As she said, "I've never felt this close to another human being, ever. People say we're co-dependent but we just want to be together all the time."

Osbourne and Mosshart were planning to marry at her family's home in England, with Osbourne admitting hopes that her mother would take over the entire event. Osbourne said, "We're thinking, 'Let's just have my mum plan it, and we'll just show up.' She's the best at that kind of stuff" (via People).

A year later, the couple called the whole thing off. As a representative for Osbourne explained to Us Weekly, "The split is amicable, and the pair continue to have nothing but the utmost respect for one another. Kelly is looking forward to a new year full of fresh beginnings."

Months after her ill-fated engagement to chef Matthew Mosshart ended, Kelly Osbourne found herself in a brand-new relationship. She and British model Ricki Hall moved in together in July 2014, and Osbourne was only too happy to share a very intimate photo of the two embracing (via the Daily Mail) for all her fans to see.

However, things between Osbourne and Hall may have moved too quickly, which could have contributed to the couple's ultimate demise. The Daily Mail pointed out that Hall was previously in a relationship with fellow model Lauren Capulet in May of that year, but by June, he and Osbourne connected. A source close to the couple told Yahoo! News, "They recently started following each other on Instagram. He's got a huge beard, which Kelly finds really sexy, she loves guys with beards! She's definitely interested in seeing where it goes with him." The couple, however, would soon break up.

In 2019, Kelly Osbourne stepped with British model Jimmy Q. The Daily Mail noted that the two were spotted at London's All Point East End Festival in May of that year and that the pair attended several events together, including the U.K. premiere of "Rocketman" and the Wedgewood Garden & Tea Conservatory at the Chelsea Flower Show. 

Things between Osbourne and Jimmy Q ended roughly four months later. The Sun published a report that blamed the pair's schedules on the end of their relationship, but a source reportedly close to the relationship shared with the publication that something else was going on behind the scenes, too. As the source put it, "Kelly and Jimmy initially seemed really well suited and were incredibly smitten. But sadly, in the last few months of their relationship, they started to argue a lot."

Kelly Osbourne met cinematographer Erik Bragg after things ended with Jimmy Q. The two dated for a year before breaking up in 2021, but it appears that they remained on good terms following the end of their relationship. While Bragg declined to elaborate on what led to their split, he told Us Weekly, "Kelly rules. That's it. That's all."

Months earlier, in August 2020, Osbourne told "Hollywood Raw with Dax Holt and Adam Glyn" about her dating life. Without naming names, Osbourne said that she was really happy. According to Life & Style, she said, "Someone that I used to date and now we are hanging out again. I don't even know how to explain it. What it is, is perfect. I full-blown love him. That's all I'm saying ... For the first time in my life, I can tell you what happiness is because I've never had it before."

In May 2022, Kelly Osbourne announced that she and Slipknot musician Sid Wilson had gotten engaged and have a baby on the way. Osbourne was clearly thrilled with the news, writing on Instagram, "I am over the moon to announce that I am going to be a Mumma. To say that I am happy does not quite cut it. I am ecstatic!"

The two technically met in 1999 but didn't get into a relationship until decades later. However, in January 2022, Osbourne shared a series of photos of Wilson in honor of his birthday, and a source told People that things between the two were good. As the source put it, "Kelly and Sid met when his band was touring with Ozzfest in 1999. They have remained friends since. They are very happy together."

A month later, Osbourne herself celebrated the relationship on Instagram, where she wrote, "After 23 years of friendship I can't believe where we have ended up! You are my best friend, my soulmate and I am so deeply in love with you Sidney George Wilson."