Let’s face it: Kelly Osbourne’s dating history has been nothing short of a roller coaster. We can only image how confusing this must’ve been, with several whirlwind romances and heartbreaking breakups. Kelly, on the other hand, has always bounced back from her previous failed relationships, and she’s now wiser for it.
Currently, the media personality and singer appears to be seeing a fellow musician. Let’s take a peek at her relationship history before we get into those updates.
In 2002, Kelly dated Bert McCracken
Remember Kelly Osbourne and her family from the MTV reality show The Osbournes? During season two of the show, Kelly began dating Bert McCracken, the lead vocalist of The Used. The fact that his family did not approve of him added to the strain. Bert decided to call it quits by the season’s end. He truly broke up with Kelly over the phone on Valentine’s Day.
In 2003, when asked about it, he said: “I’ve been in a bad mood. I desperately want to be with her, but I can’t. I’m just not ready for a relationship in general, much less a big, public one.”
Bert’s pregnant ex-girlfriend Kate and their unborn child were tragically killed by a heroin overdose the following year. But things have improved for the singer since then. He and Kelly have reconciled, and he now resides in Australia with his wife, Ali Schneider, and their daughter, Cleo Rose McCracken.
In 2006, Kelly had a relationship with Matty Derham
Matty Derman, a member of the band Fields, is said to have dated the TV celebrity for a short time and even attempted to marry him. Her parents were furious when word of their wedding spread during the Electric Picnic Festival in Ireland. The ceremony, however, wasn’t legally binding, according to her spokesman.
Gary Farrow, her publicist, stated: “Kelly Osbourne was rumored to have married at a festival in Ireland over the weekend, according to a number of rumors that circulated swiftly. This is completely false, and the inflatable church that performs these non-legally binding mock marriages for entertainment is as real as it gets.”
Maybe it was for the best, for the couple divorced in January 2007.
In 2006, she was thought to be dating Kevin Zegers
Although neither of them publicly announced if they were dating, they were seen together on several occasions and appeared to be a pair. They were spotted running errands and hanging out in Los Angeles, according to multiple sources. But, if they were together, it was most likely simply a flirtation.
In 2008, the singer moved on to Danny Jones of McFly
She was observed at a nightclub with British musician Danny Jones, and a source claimed that at the end of the night, they were “all over each other.” Danny, on the other hand, revealed that nothing happened that night. Kelly invited him back to her apartment after the club, and things went south from there.
He didn’t appear impressed when he met Kelly’s father, Ozzy.
“We were downstairs till about 7 a.m. chatting and whatnot,” Danny recalled. Then Ozzy Osbourne walked in, simply wearing these crumpled black Y-fronts. ‘Who are you, then?’ he snarled as he sat next to me at the kitchen table, wolfing down a couple of buns.
“I Ieft soon after he returned to bed, even though Kelly wanted me to stay,” he added. I’m the type of kid who prefers to fully introduce himself to parents before staying the night. It wasn’t quite right…. Kelly, for whatever reason, never contacted me again. She’s become too cool for me.”
Kelly and Luke Worrall got engaged
The couple got engaged in November 2008 after dating for a few months in 2008. Kelly, on the other hand, was not in a hurry to marry the British model, opting to take her time with the arranging.
This proved to be an excellent decision, but for the worst conceivable reason. In 2010, Jessica called off their engagement after reports circulated about Luke cheating on her with model Elle Schneider.
She said: “It was quite humiliating. Everyone kept telling me Luke was cheating on me, but I was never convinced.”
Kelly allegedly had a five-second relationship with Josh Hansen
Kelly was pictured at a restaurant with motocross rider Josh Hansen just a month after ending her relationship with Luke. They left in the same vehicle, which naturally sparked romance suspicions. Despite the fact that neither of them declared they were dating, it was claimed that they were spending more time together.
Stephanie Pratt, Josh’s ex-girlfriend (who also happens to be Kelly’s best friend), was not pleased to hear the reports.
She claims she found out about them allegedly dating only a week after Kelly had consoled her through the breakup. She said: “I saw a news story about Kelly Osbourne and Josh Hansen dating! Part of me was relieved to have decided that this guy was worthless, but the majority of me feels heartbroken.”
Kelly and Josh’s supposed affair ended almost as fast as it had begun.
In 2011, she reportedly had affairs with Rob Damiani and Quincy Combs
It’s unclear how long these purported relationships lasted, but tabloids claimed Kelly was dating two men.
“Kelly was basically in a state of depression at the beginning of the Christmas season, but went out one night over the holiday break and met a new guy who really turned her around… [Rob] seemed genuinely interested in getting to know her, and this brought her out of her shell,” one source revealed about Rob.
Another report stated she was hooking up with Quincy, Diddy’s stepson. Kelly, on the other hand, stated that these were only hearsay.
She said: “I had two boyfriends when I woke up yesterday morning. ‘Oh, that’s cool!’ I said. That’s fantastic! Thank you for making me appear cool.’ But where do they acquire this information? According to the media, I have not one, but two boyfriends.”
In 2011, she began dating Anton Lombardi, a longtime friend
In May, the former Australia’s Got Talent judge was photographed holding hands with the photographer in New York, and yep, it looked precisely like that.
According to one source: “Kelly and Anton Lombardy had been friends for a long time, but their relationship only turned serious about a week ago. The events unfolded naturally. They became friends in New York and have recently moved to Los Angeles together. Kelly’s pals are ecstatic for them; he’s a fantastic, talented individual.”
Despite the fact that their burgeoning romance sounded good, it ended prematurely.
Kelly and Matthew Mosshart got engaged
Kelly initially met the vegan chef in 2011 during Kate Moss’ wedding, and they hit it off right away. They got engaged after two years together, and Kelly said, “We simply want to be together all the time.”
However, by 2014, they had both decided to end their relationship.
“It was a joint decision,” she explained. We are deeply in love with one other. It simply wasn’t the right moment for us, and I believe that if we hadn’t been as mature and adult as we are, we would have ended up on a less than pleasant path.”
Despite the separation, she said they remained “very close friends.”
In 2014, Kelly began dating Ricky Hall
Six months after Kelly and Matthew announced their split, news of their new romance broke. According to one source: “Kelly thinks his beard is quite attractive. She’s very curious to see how things progress with him.”
This romance, however, was short-lived.
In 2016, Kelly went on to Kes Glozier
She met Kes, the editor-in-chief of The New British magazine, through common friends, and after a few months of getting to know each other, they began dating. It was never stated when this relationship ended, but given how they simply stopped hanging out together, it’s safe to assume it ended discreetly.
Kelly had a four-month relationship with Jimmy Q
Kelly and the model began dating in early 2019 and were seen together at a number of events. Unfortunately, this relationship did not last.
“Kelly and Jimmy Q originally seemed wonderfully well suited and were incredibly infatuated,” a source added. However, in the last few months of their relationship, they began to fight often. It was only natural for them to separate because they desired different things.”
Is Kelly Osbourne dating someone else now?
“[I’m] taking the’me’ time,” she declared after her separation with Jimmy Q. I can’t be good to anyone unless I’m good to myself. I believe that love takes a lot of effort. It’s a lot of work, and I want to [find love again] one day.”
She began dating Erik Bragg not long after the divorce. They had been dating for about a year.
Kelly looks to have found love once more, this time with Slipknot’s Sid Wilson. In an Instagram post, she acknowledged their relationship by wishing him a happy birthday.