Lauren Silverman flashes her impressive engagement ring after Simon Cowell ...

Lauren Silverman flashes her impressive engagement ring after Simon Cowell ...
Lauren Silverman flashes her impressive engagement ring after Simon Cowell ...

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. 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)

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 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

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)

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

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.

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