We look back at the highs and lows of the X Factor creator’s complicated love life- from failed engagements to warring ex-girlfriends to his affair with Lauren…
Paula Hamilton (1977)
In 2011, model Paula, 60, one of the most famous faces of the 1980s, revealed that she lost her virginity to Simon. They dated in the 1970s and were childhood sweethearts (pictured in 1991)
In 2011, model Paula, 60, one of the most famous faces of the 1980s, revealed that she lost her virginity to Simon.
The star of the decade’s iconic Volkswagen Golf TV commercial said she was 16 at the time.
She told Daily Mail Weekend magazine that she lost her virginity to ‘a boy called Simon’.
Paula and Simon were childhood sweethearts while growing up in Hertfordshire in the 1970s, she said.
She also claimed, in contrast to his Mr Nasty image on TV, he was ‘very, very protective’ and stopped teachers vilifying her.
She went on: ‘I couldn’t read or write until I was 11. So I was called stupid and bullied by teachers. Simon was really important to me because he stopped them picking on me.’
Jackie St Clair (1970s)
Ex: Former Page 3 model Jackie dated Simon in the 1970s and maintained a strong friendship with Simon- even after they split (pictured in 2002)
Former Page 3 model Jackie dated Simon in the 1970s and maintained a strong friendship with Simon- even after they split.
Over the years she has travelled on holiday with him. She reportedly had an ongoing feud with Sinitta. Back in 2012 it was reported Sinitta flew home from Barbados early to avoid a showdown with Jackie after their famous fight in 2010.
At the time of the original fight, Sinitta accused Jackie of ‘evil lying’ by Sinitta as a row brewed over gossip surrounding Simon and the status of his engagement to his then girlfriend, Mezhgan Hussainy.
Sinitta believed that Jackie was blaming her for leaking stories about Simon and his Mezhgan.
Sinitta (The on-off 20 year romance)
In 2020, Sinitta suggested her on-off romance with Simon was ‘never really over’ until he had son Eric with girlfriend Lauren Silverman in 2014 (pictured 1980s)
In 2020, Sinitta suggested her on-off romance with Simon was ‘never really over’ until he had son Eric with girlfriend Lauren in 2014.
The pair had an on-off romance for 20 years after first meeting in the 1980s.
When asked when her and Simon had ‘finally called it quits’ on their love affair, the singer, 58, told New! Magazine: ”There was always an element of “well, it’s never really over.”
‘But when Eric was born that was it. I would never come between his family.’
Whole lot of history: The pair had an on-off romance for 20 years after first meeting in the 1980s
Discussing the ructions caused between her and Simon, she added: ‘[Lauren] and I were best friends. I’m really happy for them, but it was hard and caused a fallout.
Sinitta said she had a long-held belief that once Simon had stopped dating other women, they would eventually end up together, adding that she would have married him and ‘never’ fell out of love with him.
The pair have also been through shared heartache as Sinitta admitted she was still very close to the mogul, after revealing in 2013 she was previously forced to abort their baby in the 1980s following health complications.
Rollercoaster: Sinitta has previously said she believed she would marry the mogul (pictured 2013)
Simon Cowell And Louise Payne (1995)
It was previously reported Cowell was secretly engaged to Page Three girl Louise Payne, after she split from husband and Right Said Fred star Fred Fairbrass
It was previously reported Cowell was secretly engaged to Page Three girl Louise Payne, after she split from husband and Right Said Fred star Fred Fairbrass.
But their three-year relationship ended when the buxom blonde said she wanted to start a family with Cowell, but he was too busy.
Cowell apparently popped the question to the now-43-year-old in a lift during a business trip to New York, reported the Daily Star.
The pair met at a function in London in in 1995, after the end of Louise’s marriage to guitarist Fred, now 68.
They allegedly first exchanged numbers at the party which Cowell was attended with his brother Nicholas.
But during their first date, he had the flu and thought he had blown his chances. A year later they bumped into each other and began a romance.
The source added: ‘The relationship had its ups and downs. They split twice but he was so in love with her he kept trying to make it work.
‘After the third attempt, they split for good. It was just before he started on Pop Idol. Louise wanted kids and he knew he wasn’t ready.
‘He never stopped loving her, though. He was heartbroken.’
Simon And Georgina Law (2000)
Fling: The X Factor judge had a casual fling with former Page 3 model and dancer Georgina, who later spoke about their whirlwind romance
The X Factor judge had a casual fling with former Page 3 model and dancer Georgina, who later spoke about their whirlwind romance.
She said: ‘I met Simon at the Spearmint Rhino Club where I used to work occasionally. This was before Pop Idol so he wasn’t famous. He is a lovely man and we had a casual relationship for about six months.
‘We weren’t proper boyfriend or girlfriend, but we’d see each other regularly’.
Terri Seymour (2002- 2008)
Friendliest of exes: Simon has remained close friends with ex Terri ever since they dated from 2002 to 2008 (pictured in 2004)
Simon has remained close friends with ex Terri ever since they dated from 2002 to 2008, and he even threw a birthday party for her daughter Coco last year.
While Terri and Simon reportedly split over his desire to not have a brood – his situation is very different now, with him admitting in 2017 that their children often share playdates.
Terri has six-year-old daughter Coco with model boyfriend Clark Mallon, 29.
Terri and Simon were an item for eight years before their split, with the music mogul rumoured to have given her a £6million ‘parting gift’.
Simon And Dannii Minogue (2007)
Chemistry: In 2012, it was revealed Simon felt ‘genuine love’ for Dannii Minogue, 50, after a fling with the singer in 2007 (pictured in 2010)
In 2012, it was revealed Simon felt ‘genuine love’ for Dannii Minogue, 50, after a fling with the singer in 2007.
The music mogul admitted he felt ‘like a schoolboy’ around the Australian star during her time as a judge on the X Factor.
Details of the romance were revealed in a book entitled The Intimate Life Of Simon Cowell, written by former BBC journalist Tom Bower.
In the book, there were several quotes from Cowell speaking about the romance – even though Dannii and Simon had both denied it in 2008.
He is quoted as saying: ‘I had a crush on her. It was Dannii’s hair, the sexy clothes and the t**s. I was like a schoolboy. She was foxy. She was a real man’s girl. Very feminine.’
Mezghan Hussainy (2009- 2012)
Engaged: Simon went on to become engaged to Afghan-born make-up artist Mezhgan Hussainy in 2010, but they split in February 2012 (pictured in 2020)
Simon went on to become engaged to Afghan-born make-up artist Mezhgan Hussainy in 2010, but they split in February 2012.
The split only became public knowledge when Tom Bower published his unauthorised biography Sweet Revenge: The Intimate Life Of Simon Cowell.
The judge confessed in the book that he made a mistake asking her to marry him: ‘We came to the conclusion that I’m a hopeless boyfriend.’
He was reported to have given Hussainy a £5million mansion in Beverly Hills as compensation for the embarrassment of cancelling the engagement.
Carmen Electra (2012)
Lovestruck: In 2012, Simon confirmed he was dating former Baywatch star Carmen, 49 (pictured in 2012)
In 2012, Simon confirmed he was dating former Baywatch star Carmen, 49, however she didn’t get an invite to the star’s annual Caribbean jaunt in January 2013, as he was doted on by his coterie of exes.
Carmen who met Cowell when she was a judge on BGT said she ‘adored’ the X Factor supremo, but while he admitted they are dating he was very clear about the status of their relationship.
The music mogul told American Idol host Ryan Seacrest on his radio show: ‘She’s not my girlfriend. We’re people who date.’
Simon And Lauren Silverman (2013- now)
Congratulations! Simon proposed to his partner of eight years in front of their son Eric, seven, and Lauren’s son Adam, 16, from a previous relationship (pictured in November)
Simon proposed to his partner of eight years in front of their son Eric, seven, and Lauren’s son Adam, 16, from a previous relationship.
A source said: ‘Whilst Simon never thought he was the marrying type, he’s realised he’s met the woman of his dreams – and couldn’t be happier’
Simon met Lauren in 2013 when she was still married to millionaire property developer Andrew Silverman with news of the affair making global headlines.
Despite previously insisting that he ‘didn’t believe’ in marriage, the father-of-one reassessed his views after falling in love with Lauren – who was left ‘stunned’ by the shock proposal.
A source told The Sun: ‘Lauren was absolutely stunned and never in a million years expected Simon to pop the question. She burst into tears – happy tears – and obviously said yes straight away.
‘Lauren has been Simon’s rock over these past few years – supporting him when he broke his back, and through thick and thin generally. They make a wonderful couple.
‘Whilst Simon never thought he was the marrying type, he’s realised he’s met the woman of his dreams – and couldn’t be happier. In the words of Beyoncé, it was time to put a ring on it.’