KellyOsbourneand Sid Wilsons Relationship Timeline

A friends to lovers romance. Kelly Osbourne met her boyfriend, Sid Wilson, two decades before they started dating — and it was all thanks to dad Ozzy Osbourne.

The U.K. native met Wilson in 1999 when his band Slipknot toured with Ozzfest — the music festival founded by the “Shut Up” singer’s parents. The pair developed a friendship that lasted for over two decades before officially confirming in February 2022 that their relationship had turned romantic.

“After 23 years of friendship I can’t believe where we have ended up!” the Dancing With the Stars alum wrote in a February 2022 Instagram post. “You are my best friend, my soulmate and I am so deeply in love with you Sidney George Wilson.”

Wilson, for his part, made his own post about the Emmy Award winner.

“There [are] not enough colors to display the palette of Love I have for you in my Heart. Happy Valentines Day my Love XoXo,” the Iowa native wrote to his girlfriend the same day.

In May 2022, Osbourne announced she is expecting her first child.

“I know that I have been very quiet these past few months so I thought I would share with you all as to why… I am over the moon to announce that I am going to be a Mumma,” the Osbournes alum wrote via Instagram at the time. “To say that I am happy does not quite cut it. I am ecstatic!”

The Life as We Know It actress also shared two photos of her sonogram along with the news, including one of her gazing at the photo of her future child by the pool.

The news comes a year after Osbourne opened up about her addiction, explaining during an appearance on Red Table Talk that she feels like she wasted time not focusing on her sobriety.

“I feel very behind. As a woman I would have loved to be married and have children by now,” the Fashion Police star revealed. “My brother [Jack Osbourne] has three daughters, and I would have loved to have a few kids by now, but that wasn’t what was in the cards for me yet.”

She continued: “And I would have been no kind of mother at all because I was that crazy addict who was like, ‘Oh I will just stop doing drugs when I get pregnant because I have to.'”

Before falling for Wilson, Osbourne had a variety of whirlwind romances and heartbreaks. The fashion designer was previously engaged to Luke Worrall in 2008 before calling it quits in 2010 after he allegedly cheated on her with model Elle Schneider.

“He is the worst thing that ever happened to me…I have never felt heartbreak like this in my life. I only came home for Xmas to see him meanwhile he has been f—ing hundreds of girls as well as men behind my back,” the singer tweeted following the incident.

The reality star’s second engagement came a year later in 2011 after meeting vegan chef Matt Mosshart at Kate Moss’ wedding. The two were together for three years before ultimately deciding to part ways in 2014.

“It was a mutual decision,” she explained to E! News at the time. “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.”

The So Undercover star’s last relationship before Wilson was with Eric Bragg, whom she dated for a year before calling it quits in October 2021. The former couple, while typically private, flaunted their relationship via Instagram Story that January when they washed the cinematographer’s car before the TV personality gave her then-beau a few tips.

“You want to make a balloon animal so every time you look at it, it looks like a frog,” she noted at the time, explaining how to correctly store a hose after use.

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Bragg declined to comment on their split, but told Us of his ex at the time, “Kelly rules. That’s it. That’s all.”

Scroll through to see more of Osbourne and Wilson’s friends to lover’s romance:

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