Inside Kelly Osbourne's Dating History

Sun Jun 25 2023
By   tashi

Kelly Osbourne's romances over the years: The singer-turned-fashionista is a mother to one!  

Best known as the daughter of power couple Ozzy Osbourne and Sharon Osbourne, Kelly Osbourne has more credit to her name than just being a famous scion. She is a television personality, actress, singer, model, and fashion designer.  

Throughout her life in the spotlight, Osbourne has attracted attention on several occasions; be it her various endeavors, or unfiltered, and often problematic remarks in interviews. The actress recently sparked a massive fiasco for calling Prince Harry a "f---ing t---".  

Inside Kelly Osbourne's Dating History!   

Kelly Osbourne has never been far away from some A-level controversy and unfortunately, her past romantic endeavors had a lot to do with the actress's built-up image as a disputed royalty. The Fashion Police star dated musician Bert McCracken on and off for a brief time. The couple's romance was even showcased in the Osbourne family's show, The Osbournes.   

Kelly Osbourne is an actress and singer.
Kelly Osbourne is the daughter of Ozzy and Sharon Osbourne. Photo Source: Instagram

The duo's split sent the media into a frenzy after The Used frontman revealed that he broke up with Osbourne over the phone. "I'm just not ready for a relationship, period, let alone a huge, public relationship," McCracken said while seemingly insinuating that their televised romance was the problem.  

After getting her heart broken by the musician, Kelly had a short-term romance with musician Matty Derman in 2008. The Dancing with the Stars alum was next linked with Danny Jones, who she allegedly dated in 2008. Although fans didn't hear much of their romance or how it ended, Jones hinted at Ozzy's involvement in their split.  

Kelly Osbourne has been engaged twice.
Kelly Osbourne has been engaged twice. Photo Source: Instagram

According to the little muddled info revealed by Jones, the Black Sabbath hitmaker probably sabotaged his daughter's budding romance with Jones. Kelly's first notable relationship was with model Luke Worrall, who she even got engaged at one point.    

But the pair's romantic stint couldn't have ended any worse, with Osbourne accusing Luke of cheating on her, and the model, five years her junior, throwing shade at her on social media. The Project Catwalk alum, who now had cemented a reputation as a serial dater, took a year off the dating pool before jumpstarting another stint.   

Osbourne was looking forward to marrying Matthew Mosswart before abruptly calling it quits with him!  

Kelly dated and even moved on with musician Rob Damiani in early 2011. But it wasn't long before the actress-turned-designer realized that it wasn't meant to be. Love knocked on Kelly's door again and the actress started seeing chef Matthew Mosshart in early 2013.   

Kelly Osbounre dated Rob Damiani.
Kelly's first fiance, Luke Worrall, cheated on her. Photo Source: Instagram

The duo's whirlwind romance escalated into an engagement. Gushing about her incoming wedding with the chef, the Shut Up crooner said, "I've never felt this close to another human being, ever", only to find herself back at square one after a year of engagement. "The split is amicable," said a source.  

The Osbournes star weathered a few more heartbreaks before landing the one. She was with British model Jimmy Q in 2019. The duo seemed smitten at first but the romance fizzled out after a few months. Kelly's other noteworthy relationship was with cinematographer Erik Bragg, who she dated for a year. Bragg is one of the few exes, who Kelly shares a cordial bond with. 

Kelly Osbourne Found Love Again!  

Kelly has found love again and this time, fans have a feeling that it'll last. The So Undercover actress started dating DJ/musician Sid Wilson in 2022. The duo had known each other for over two decades after meeting at the 1999 Ozzfest. Kelly and her new beau sparked dating rumors after Osbourne wished Sid his 45th birthday last year.    

Kelly Osbourne is dating Sid Wilson.
The singer started dating musician Sid Wilson last year. Photo Source: Instagram

Osbourne has since been regularly updating fans on her healthy romance with Wilson. Kelly commemorated their first Valentine last year with a loved-up snap of the two, made more romantic with her sweet caption. "After 23 years of friendship, I can't believe where we have ended up," the singer wrote.  

The Brit even opened up to the idea of motherhood with her new beau and revealed her pregnancy in May 2022. "I am over the moon to announce that I am going to be a Mumma," Kelly wrote alongside a picture of a sonogram. The pair became first-time parents in October 2022, with the birth of their son, Sydney.   

Kelly welcomed a son with Wilson.
Osbourne and Wilson welcomed their firstborn in October 2022. Photo Source: Instagram

The Osbournes star is still over the clouds with her son's arrival and often posts him on her social media. Fans are now looking forward to the actress announcing her engagement with Sid. Kelly's boyfriend and the father of her son, Wilson, is best known for headlining the heavy metal band, Slipknot.  

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