How Kelly Osbourne battled two broken engagements to find love with ‘best friend'…and why proposal may raise red flags

Scottish Sun

07-07-2025

Click to share on X/Twitter (Opens in new window)
Click to share on Facebook (Opens in new window)
SHE'S battled her fair share of heartache - including two failed engagements and very public battles with addiction.
But over the weekend, Kelly Osbourne took one almighty step towards her happy ever after, when her boyfriend of three years - Slipknot rocker Sid Wilson - got down on bended knee and asked her to marry him.
13
Sid got down on bended knee in front of Kelly's friends and family
Credit: instagram/kellyosbourne
13
Proud parents Sharon and Ozzy Osbourne looked on - shortly after Ozzy brought the house down at Villa Park in Birmingham
Credit: instagram/kellyosbourne
13
The happy couple share two-year-old Sidney
Credit: Getty
And, clearly not one to shy away from a very public proposal, Sid popped the question on what was already a very momentous night - her dad Ozzy Osbourne's final Black Sabbath concert in Birmingham.
This, of course, sent keyboard warriors reeling. Some celebrated Kelly's big news, while others worried that it overshadowed Ozzy's big night.
Speaking exclusively to The Sun, behavioural psychologist and relationship expert Jo Hemmings weighs in.
According to her, it's no surprise that the move split the internet - leading some to brand it a "red flag".
'Of course, the timing of the engagement - during her father Ozzy Osbourne's farewell concert - has sparked gossip about whether Kelly was 'stealing his limelight', even though she was apparently surprised by the proposal,' Jo tells us.
'But I'd argue it's more layered than that.
"Kelly has always been fiercely loyal to her family; if she had some insight into what was about to happen, choosing that moment could well have been her way of honouring the man who shaped so much of her life.
'Rather than overshadowing him, it entwined her father's legacy with the next chapter of her own.'
She adds: "That said, others may see it as signs of jealousy, possessiveness or 'new ownership rights' in front of her dad at such a significant moment."
But other cynics said it was a worrying sign of things to come - and that he might continue to assert himself at inopportune moments.
13
Kelly was previously friends with the Slipknot rocker for over 20 years before getting together in 2022
Credit: Getty
Jo adds: "If the proposal was a genuine surprise to Kelly, which she claimed it was, then Sid was taking something of a risk in asking her to marry him at her dad's farewell gig.
"The attention should really have been on Ozzy.
"There was certainly nothing spontaneous about it, clearly pre-planned, which could indicate control issues further down the line, so there's a possible red flag there."
Taking to Instagram over the weekend, Kelly, 40, who shares two-year-old son, also named Sidney, with her rocker boyfriend, posted a video of the special moment.
In the clip, Sid, 48, could be seen turning to her backstage, surrounded by family and friends including her parents Sharon and Ozzy, and her brother Jack.
He told her: "Kelly, you know I love you more than anything in the world…' at which point Ozzy chimed in, joking, "F*** off, you are not marrying my daughter!"
13
She's said that becoming a mother is 'the best thing that ever happened to me'
Credit: Eroteme
13
Kelly first rose to prominence with her family - pictured together in 2015 - in the early noughties
Credit: Getty
13
Kelly has faced her fair share of heartbreak
Credit: Instagram/Kelly Osbourne
Amid uproarious laughter, Sid continued: "I want to spend the rest of my life with you - and ask in front of all of our family and friends, Kelly, will you marry me?"
He then placed a stunning 18K yellow gold ring on her finger, prompting a clearly stunned Kelly to leap into his arms, as their loved ones cheered them on.
Kelly's comments were duly filled with well wishes from friends and fans alike.
TV personality Rylan Clark wrote: 'OMG Kel!!! Congraaatttsssss' while celebrity blogger Perez Hilton added: 'Awwwww. Congratulations!!! Love is such a blessing!'
It was Ozzy's day, not hers
Unimpressed fan
However, amid the joy and jubilations, some people were quick to slam the timing of the proposal - questioning whether it really was the right moment for Sid to make his move.
As one fan put it: 'Make it about ME! ME ME ME! Poor Ozzy.' Another unimpressed commenter weighed in: 'It was Ozzy's day, not hers.'
After all, it was already a seismic day for the whole Osbourne brigade - even before it ended with the shock proposal.
Rock icon Ozzy first rose to fame in the late 1960s with rock band Black Sabbath - paving the way for heavy metal music and putting their hometown Birmingham on the map as the 'home of metal'.
Then, in 2002, he and his family changed the game for reality TV with their eponymous fly-on-the-wall series The Osbournes - long before the Kardashians came on the scene.
Viewers instantly fell in love with the family's potty-mouthed antics, rude British humour - which stuck out even more in their LA bubble - and the dynamics between the matriarch Sharon, a baffled and bumbling Ozzy, and then rebellious teens Kelly and Jack.
They also have an older sister, Aimee, who chose not to be featured on the show.
However, despite their fame and fortune, the family have been beset by a huge amount of challenges over the years - including Ozzy, Kelly and Jack's own addiction battles, and Ozzy's Parkinson's diagnosis, which he made public in 2020 (he'd actually secretly fought the disease since 2003).
This followed his near-fatal quad bike accident in 2003, which left him with a broken neck vertebra, a broken collarbone, and broken ribs; a severe fall at home in 2019, which significantly aggravated his spinal and neck injuries, and his subsequent battle with pneumonia.
All this has had a massive impact on the ailing rocker - which made his final public performance on Saturday night all the more poignant.
Ozzy's farewell
The event at Birmingham's Villa Park, named Back To The Beginning, also featured a mega line-up of fellow rock stars including Guns N' Roses, Metallica, and Alice in Chains - all paying tribute to the group - and the man - that started it all.
But it was Ozzy who quite rightly stole the show, which raised money for Cure Parkinson's, Birmingham Children's Hospital and Acorn Children's Hospice.
Taking to the stage at the end of the night on a black throne, emblazoned with his signature bat motif (after he famously bit one's head off during a concert in 1982) an emotional Ozzy sang his heart out as he bid farewell to live performing.
13
Ozzy received a rapturous applause as he bid his fans farewell with his final concert
Credit: ROSS HALFIN
13
His ailing health has done nothing to dampen his rock and roll spirit
Credit: ROSS HALFIN
His loving family were all there to support him, all overseen by proud wife Sharon - who has managed her husband's career for the past 46 years and has stood loyally by his side, despite revelations of his infidelity over the years.
So, the question is - on such a significant night for Ozzy and the whole family - was it really the right time and place for Kelly to get so publicly engaged?
Some cynics didn't like the apparent upstaging of the affair.
It entwined her father's legacy with the next chapter of her own
Relationship expert Jo Hemmings
But, as Jo reminds us, given that the family are so tight-knit and close, it might just have been the most appropriate time imaginable.
Every parent ultimately wants to see their child find happiness - and Sharon and Ozzy are undoubtedly no different.
Let's remember, Kelly's had some false starts in the love department over the years.
Dating drama
In the early 2000s, she dated Bert McCracken, the frontman of the band The Used.
Then, in 2008, she started a relationship with model Luke Worrall.
The pair dated for two years, and even got engaged - but they split in 2010, after it emerged that Luke had cheated on her with a trans woman, Elle Schneider.
Elle said at the time, 'He always insisted to me he was single and I had no idea he was engaged to Kelly Osbourne.'
Meanwhile, Kelly was devastated when she found out. Taking to Twitter after dumping her cheating ex, she wrote: 'Luke Worrall is the biggest piece of s**t .
'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*****g hundreds of girls as well as men behind my back.'
13
Kelly was engaged to model Luke Worrall before he cheated on her
Credit: PA:Press Association
13
She was later engaged to Matthew Mosshart - though their split was more amicable
Credit: Getty - Contributor
In the aftermath, the TV star - who had already been to rehab several times by then to battle her addiction to prescription pills - said she was determined not to relapse.
She threw herself into her career, becoming co-host of E!'s Fashion Police and focusing on her health and wellness. However, she had a tumultuous period of pill taking, until finally getting sober in 2017.
Meanwhile, her dating life was a mixed bag. She dated vegan chef Matthew Mosshart from 2011 to 2014, and even got engaged to him too.
However, they amicably split in January 2014, with Kelly saying at the time, 'We love each other very much. It just wasn't the right time for us.'
Kelly then dated director Kes Glozier for about a year, and - in 2020 - was linked to cinematographer Erik Bragg.
Sadly, around the same time, the star suffered a relapse in 2021 - amid lockdown. She told fans that she'd fallen off the wagon after four years of sobriety, but was back on track again with her recovery.
And she hasn't looked back since - owed, partly, to her now fiancé, Sid.
In a world where relationships are so often fleeting, superficial and fundamentally incompatible, Kelly's story carries an emotional depth
Relationship expert Jo Hemmings
Kelly and the Slipknot star had actually been friends for over 20 years before they took their friendship to the next level in 2022.
Their son was born later that year, prompting Kelly to tell her fans that becoming a mum 'is the best thing that ever happened to me.'
She's also frequently heaped praised on her partner, calling him 'My best friend, my soulmate,' and adding, 'After 23 years of friendship, I can't believe where we have ended up!'
As Jo tells us: 'Kelly's journey to love is a heartwarming reminder that sometimes the person you're truly meant to be with has been by your side all along.
'In a world where relationships are so often fleeting, superficial and fundamentally incompatible, Kelly's story carries an emotional depth that's impossible to ignore.
'After two failed engagements that played out under the harsh scrutiny of the public eye, it's significant that she's found her safe haven in someone who's been her best friend for 23 years.
13
The star, who's battled addiction in the past, says she's happier than she's ever been
Credit: Getty
13
Friends and fans agree she seems more settled and happier since getting together with Sid
Credit: Shutterstock Editorial
'This speaks to a profound foundation of trust, understanding and shared history - the bedrock that so many relationships lack from the outset.'
Sid, for his part, may be a rock star, but - before getting together with Kelly - he preferred a more private lifestyle.
Indeed, he's known for wearing his infamous mask as the frontman of his heavy metal band.
Sure, some fans were surprised that he chose such a public moment to propose to Kelly - suggesting, again, that he was doing it because he knew it would make the family happy.
There could be control issues further down the line
Relationship expert Jo Hemmings
However, weighing it up, she reckons that the fact that Sid's known Kelly - and her family - so long suggests he took a calculated risk and it seems to have paid off.
She tells us: 'If Sid barely knew Kelly, or had no real profile of his own, then it would definitely be a red flag.
'But Ozzy obviously has known Sid for some time and his brilliant response 'F**k off, you're not marrying my daughter' mid-way though the proposal is typical Ozzy style.
"It's both outrageous and witty, but with typical Osbourne family warmth at the same time.'
The bottom line is that Kelly's clearly happier than she's ever been before - and her family have all shared a very memorable, and moving, few days.
Whether the proposal happened at the right time or not is a matter of opinion. But the fact that it happened is reason to celebrate.
The question is, how will Ozzy get his own back on their wedding day?