From failed engagements to feuding ex-girlfriends to his romance with Lauren…
Paula Hamilton (1977)
In 2011, 60-year-old model Paula, one of the most famous faces of the 1980s, revealed that she had lost her virginity to Simon. They dated in the 1970s and were childhood sweethearts (pictured in 1991).
In 2011, 60-year-old model Paula, one of the most famous faces of the 1980s, revealed that she had lost her virginity to Simon.
The star of the legendary Volkswagen Golf TV ad revealed that she was 16 at the time.
She told Daily Mail Weekend magazine that she lost her virginity to “a boy named Simon.”
According to her, Paula and Simon were childhood sweethearts growing up in Hertfordshire in the 1970s.
She also claimed that, in contrast to his portrayal of Mr. Nasty on television, he was “very, very protective” and did not allow teachers to vilify her.
She continued, “I couldn’t read or write until I was 11. So the teachers called me stupid and bullied me. Simon was very important to me because he stopped them picking on me.”
Jackie St. Clair (1970s)
Example: Former model Jackie dated Simon in the 1970s and maintained a strong friendship with Simon even after they broke up (pictured in 2002).
Former model Jackie dated Simon in the 1970s and maintained a strong friendship with Simon even after they broke up.
For many years she traveled with him on vacation. She reportedly had an ongoing feud with Sinitta. Back in 2012, it was reported that Sinitta flew home early from Barbados to avoid a showdown with Jackie after their famous fight in 2010.
During the initial fight, Sinitta accused Jackie of Sinitta’s “evil lies” as there was a scandal over Simon’s gossip and the status of his engagement to his then-girlfriend, Mezhgan Husseini.
Sinitta believed Jackie was blaming her for leaking the stories about Simon and his Intergun.
Sinitta (At times 20 year romance)
In 2020, Sinitta suggested that her intermittent romance with Simon “never ended” until his son Eric was born in 2014 with girlfriend Lauren Silverman (pictured in the 1980s).
In 2020, Sinitta suggested that her intermittent romance with Simon “never ended” until his son Eric was born in 2014 with girlfriend Lauren.
The couple had an affair for 20 years after they first met in the 1980s.
When asked when she and Simon “finally ended” their romance, the 58-year-old singer told New! Magazine: “There’s always been a ‘well, it never really ends’ element.”
“But when Eric was born, it was like this. I would never get between his family.
The Whole Story: The couple had an affair for 20 years after they first met in the 1980s.
Discussing the quarrels between her and Simon, she added:[Lauren] and I were best friends. I am very happy for them, but it was hard and caused conflict.
Sinitta said she had a longstanding belief that once Simon stopped seeing other women, they would end up together, adding that she would marry him and “never” stop loving him.
The couple also endured shared heartache as Sinitta admitted she was still very close to the mogul after it was revealed in 2013 that she had previously been forced to abort their child in the 1980s due to health complications.
Roller coaster: Sinitta has previously said she believes she will marry a mogul (pictured in 2013)
Simon Cowell and Louise Payne (1995)
It was previously reported that Cowell was secretly engaged to Page Three’s girlfriend Louise Payne after she split from husband and Right Said Fred star Fred Fairbrass.
It was previously reported that Cowell was secretly engaged to Page Three’s girlfriend 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 asked the 43-year-old man in an elevator during a business trip to New York, according to the Daily Star.
The couple met at an event in London in 1995, following Louise’s divorce from guitarist Fred, now 68.
Allegedly, they exchanged numbers for the first time at a party that Cowell attended with his brother Nicholas.
But during their first date, he had the flu and thought he had missed his chance. A year later, they ran into each other and started an affair.
The source added, “There have been ups and downs in the relationship. They broke up twice, but he was so in love with her that he kept trying to make it work.
“After the third attempt, they broke up forever. This was just before he started working on Pop Idol. Louise wanted children, and he knew he wasn’t ready.
“However, he never stopped loving her. He was heartbroken.”
Simon & Georgina Lowe (2000)
Intrigue: The X Factor judge had a casual fling with former Page 3 model and dancer Georgina, who later opened up about their whirlwind romance.
The X Factor judge had a casual fling with former model and dancer Georgina, who later opened up about their whirlwind romance.
She said: “I met Simon at the Spearmint Rhino Club where I sometimes worked. This was before Pop Idol, so he wasn’t known. He is a wonderful person and we had a casual relationship for about six months.
“We weren’t really boyfriend or girlfriend, but we saw each other regularly.”
Terry Seymour (2002–2008)
Friendliest ex: Simon has remained close friends with Terri’s ex since they dated from 2002 to 2008 (pictured in 2004)
Simon has remained close friends with Terry since they dated from 2002 to 2008, and he even threw a birthday party for her daughter Coco last year.
While Terry and Simon reportedly split over his desire not to have a brood, his situation is very different now, with him admitting in 2017 that their kids often play together.
Terry has a six-year-old daughter, Coco, with model boyfriend Clark Mallon, aged 29.
Terri and Simon dated for eight years before they broke up and the music mogul was rumored to have given her a £6 million “parting gift”.
Simon and Danny Minogue (2007)
Chemistry: In 2012, it was revealed that Simon had “true love” for 50-year-old Danny Minogue after having an affair with the singer in 2007 (pictured in 2010)
In 2012, it was revealed that Simon had “true love” for 50-year-old Danny Minogue after having an affair with the singer in 2007.
The music mogul admitted he felt “like a schoolboy” around the Australian star when she was an X Factor judge.
Details of the affair were revealed in a book titled The Intimate Life of Simon Cowell, written by former BBC journalist Tom Bauer.
The book contained several quotes from Cowell talking about the affair, although Danni and Simon both denied this in 2008.
He is quoted as saying, “I was in love with her. It was Danni’s hair, sexy clothes and boobs. I was like a schoolboy. She was a fox. She was a real man’s girl. Very feminine.
Mezgan Husseini (2009-2012)
Engaged: Simon got engaged to Afghan-born makeup artist Mezhghan Husseini in 2010, but they separated in February 2012 (pictured in 2020)
In 2010, Simon became engaged to Afghan-born makeup artist Mezhghan Husseini, but they broke up in February 2012.
The split only came to light when Tom Bauer published his unauthorized biography Sweet Revenge: The Intimate Life of Simon Cowell.
The judge admitted in the book that he made a mistake by asking her to marry him: “We came to the conclusion that I was a hopeless boyfriend.”
He was reported to have given Husseini a £5 million Beverly Hills mansion as compensation for the embarrassment of calling off the engagement.
Carmen Electra (2012)
Madly in love: In 2012, Simon confirmed he was dating former Baywatch star Carmen, 49 (pictured in 2012)
In 2012, Simon confirmed that he was dating former Baywatch star Carmen, 49, however she did not receive an invitation to the star’s annual Caribbean Walk in January 2013 as he was crazy about his group of exes.
Carmen, who met Cowell when she was a judge on BGT, said she “adored” the X Factor supreme leader, but while he admitted they were dating, he was very clear on the status of their relationship.
The music mogul told American Idol host Ryan Seacrest on his radio show, “She’s not my girlfriend. We are people who meet.”
Simon and Lauren Silverman (2013-present)
Congratulations! Simon proposed to his partner of eight in front of their son Eric, seven, and Lauren’s son Adam, 16, from a previous relationship (pictured in November)
Simon proposed to his eight-year-old partner in front of their son Eric, seven, and Lauren’s son Adam, 16, from a previous relationship.
A source said: “Although Simon never thought he would get married, he realized he had met the woman of his dreams – and couldn’t be happier.”
Simon met Lauren in 2013, when she was still married to millionaire real estate developer Andrew Silverman, and news of the affair made world headlines.
Despite previously insisting that he “doesn’t believe” in marriage, the father of one changed his mind after falling in love with Lauren, who was “overwhelmed” by the shocking proposal.
A source told The Sun: “Lauren was absolutely stunned and never in a million years expected Simon to ask a question. She burst into tears—happy tears—and apparently immediately said yes.
“Lauren has been Simon’s mainstay for the past few years—supporting him when he broke his back, and generally in grief and grief. They make a wonderful couple.
“Although Simon never thought that he would get married, he realized that he met the woman of his dreams – and is very happy. According to Beyoncé, it’s time to put the ring on him.”