Kelly Osbourne Dating History: Boyfriends, Exes and More

Kelly Osbourne has a preference for musicians when it comes to relationships and she is now happily dating her longtime friend, Slipknot band member Sid Wilson.

The two have known each other for over 20 years, according to People, which likely helped them solidify a friendship first before they started dating.

“Kelly and Sid met when his band was touring with Ozzfest in 1999,” a source told the publication in January 2022. “They have remained friends since. They are very happy together.”

The former Osbournes reality star and the Slipknot turntablist typically avoid commenting on their romance, but they gave fans a small hint upon uploading photos via Instagram of custom-made pillows designed with their faces.

“Thank you @thatpillowguy (not to be mistaken for that other guy) for our amazing pillows,” the daughter of Ozzy and Sharon Osbourne captioned a carousel post on Instagram that month. “We are #obsessed!!!! There are so many things I want to turn into pillow. I will be hounding you! Sorry in advance.”

Before sparks started flying with Sid, Kelly was in a relationship with cinematographer Erik Bragg for nearly one year. Several sources confirmed to Us Weekly that they called it quits in October 2021. While Erik declined to comment on the matter, he simply gave his ex-girlfriend a polite shout-out.

“Kelly rules. That’s it. That’s all,” he told the outlet.

In January of that year, Kelly shared an Instagram Story video that featured her and her then-beau washing his car. The TV personality was giving the filmmaker helpful tips on how to properly clean it.

“You want to make a balloon animal so every time you look at it, it looks like a frog,” she said in the clip at the time.

She previously kept Erik’s name under wraps when she credited an unnamed boyfriend during an August 2020 interview on the podcast “Hollywood Raw with Dax Holt and Adam Glyn.”

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“Someone that I used to date and now we are hanging out again,” Kelly said. “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.”

Kelly revealed that she’s expecting baby No. 1 and is “over the moon” to become a mom. “To say that I am happy does not quite cut it,” her May 2022 Instagram announcement read. “I am ecstatic!”

Scroll through the gallery to see Kelly Osbourne’s dating history.

Bert McCracken

Kelly didn’t publicly mention how long she dated the lead singer of the band, The Used, but Bert commented on why he broke up with her in a 2003 interview with Playboy magazine.
“I did it over the phone,” he confessed at the time. “I’m such a d—khead. She’s the most important girlfriend I’ve ever had. We’re best friends. It was always just so pleasant when she was around … I want to be with her, but I just can’t. I’m just not ready for a relationship, period, let alone a huge, public relationship.”

Danny Jones

The Osbournes alum was spotted hanging out with the British singer at a London nightclub in 2008. However, their bond didn’t last long, as Danny told The Mirror that year he was invited to stay at her parents’ home, leading to an awkward encounter with her father.
“[Ozzy] sat next to me at the kitchen table, wolfed down a couple of buns and grumbled, ‘Who are you, then?’ I left after he returned to bed, even though Kelly asked me to stay.”

Luke Worrall

After dating for a brief period in 2008, the male model and the former Fashion Police presenter were engaged in November of that year. Unfortunately, the engagement ended in 2010 after Kelly heard rumors of Luke cheating on her. Kelly recalled the split in a 2011 interview with Glamour UK.
“Everyone kept telling me that Luke was cheating on me, but I never believed them,” she admitted at the time.

Matthew Rosshart

After meeting the chef in the summer of 2011, the two developed a relationship and announced their engagement in July 2013, according to Us Weekly. However, they called it quits in January 2014.
“Kelly Osbourne and Matthew Mosshart have decided to end their engagement,” Kelly’s rep told the publication that month. “The split is amicable and the pair continue to have nothing but the utmost respect for one another.”

Erik Bragg

The Masked Singer alum started dating the cinematographer amid the onslaught of the COVID-19 pandemic in early 2020. While they ended their relationship in October 2021, Erik had nothing but positive comments about his ex-girlfriend.
“Kelly rules. That’s it. That’s all,” he told Us Weekly that month.

Sid Wilson

After ending her romance with the filmmaker, Kelly began a romance with her friend of over 20 years, Sid, by the start of 2022.

She even wished her new beau “Happy Birthday” via Instagram Stories in mid-January of that year.

“Kelly and Sid met when his band was touring with Ozzfest in 1999,” an insider told PEOPLE that month. “They have remained friends since. They are very happy together.”

They were last spotted in February 2022 while attending a birthday party for Kelly’s niece. While it is unclear if they are still together, she shared a tribute to him that same month. He has not yet commented on her pregnancy.