Simon Cowell's 'harem' now from vicious fights and heartbreak to £5million parting gift

Daily Mirror

23-04-2025

Simon Cowell has become a family man with Lauren Silverman after the arrival of their son Eric, but back in the day he was known for his 'harem' of female models and singers - who got stuck into plenty of drama behind the scenes
X Factor judge Simon Cowell has been dating socialite Lauren Silverman since 2013, but before settling down, he was famed for taking to the high seas with his model girlfriends past and present.
Simon and Lauren got together while she was still married to her ex-husband Andrew. Lauren is said to have already been pregnant by the time she and Andrew split, and she welcomed son Eric, now 11, in February 2014.
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While Lauren and Simon's early days were surrounded by drama, fatherhood undeniably changed him. The Britain's Got Talent boss of yore was known to trot around the globe surrounded by a host of gorgeous women - including Lauren.
Among the many women who orbited around Simon, now 65, were his exes Sinitta, Jackie St Clair, Terri Seymour and Mezghan Hussainy, with the women often partying together at his opulent mansion in Barbados or catching the sun on his 196ft Slipstream yacht.
The group of women was often referred to as Simon's 'harem,' and he seemed to love the speculation surrounding his free-wheeling love life. The mogul even appeared in Tom Bower's biography Sweet Revenge, and was quoted as saying he loved to play his ladies off against each other.
"I want to be happy, have good people around me. I want to be free and I don't want to be bored. I'm attracted to crazy women. I encourage crazy behaviour and I make them crazy. I'm attracted to certain personalities who are difficult to control, so there are tantrums, tears and fights, which is all part of the drama," he reportedly said. "My life is really odd. Every girl wants to be number one and they're very territorial. I like the fight because otherwise I'd have a dull group of girlfriends."
So, Simon switched up the 'tantrums and tears' from the harem to the tantrums and tears from his young son, but after being ditched by Simon what happened to the One Direction founder's ladies?
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Sinitta
Sinitta claimed that while the girls were all close, being called a harem was off the mark. "We're not all sleeping with him. It's as bad as calling us his b*****s. The girls are all there with partners or as friends," she once told the Daily Mail. While she claimed not all of Simon's company was sleeping with him, Sinitta, now 61, was open about her own romance with him.
The singer dated Simon on and off for 20 years and remained convinced they'd get back together for good - until Eric was born. She 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. [Lauren] and I were best friends. I'm really happy for them, but it was hard and caused a fallout."
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The 'fallout', according to Sinitta, was caused by the fact she felt betrayed by 'sister' Lauren and was 'shocked' when Simon called her to say Lauren was expecting despite still being married to property developer Andrew Silverman. 'We are very, very good friends. When you've been close friends with someone and you're calling each other sisters and family and confided all of your secrets and feelings over the years to them… Lauren was that person to me," Sinitta claimed to The Sun.
"It was sad to discover that I wasn't that person to her. I've known her for four or five years. But it's OK, we have dealt with it. I didn't cry when I heard and I certainly didn't cry, 'It should've been me'. That's a comedy sketch — not real life.'
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But despite their woes, Sinitta and Simon remain close and she's even godmother to Eric while he is godfather to her kids Magdalena and Zac, whom she adopted with ex-husband Andy Willner. Sinitta even believes that she and Simon are so tight they share a 'psychic bond' that alerted him when she secretly contracted coronavirus in 2020.
'I caught the virus after doing a club gig. Next day I felt as if I'd swallowed a packet of razor blades. I was in bed for about a week. I didn't tell Simon I was ill but it wasn't long before he got in touch," she told the Sunday Mirror. 'When he got through, Simon said, 'You've got it [the virus] haven't you?' And I said, 'How do you know?' He said, 'I knew it. I could just tell because you disappeared. I knew you didn't want to worry me.' He told me, 'We have this weird connection, I can just tell when something's wrong.'"
Aside from her high-profile personal life, Sinitta has gone on to flourish in her career. The singer has frequently featured as a guest judge and mentor on The X Factor, and has appeared on shows such as Dancing on Ice, Celebrity Big Brother, Late Night Lycett, Celebs Go Dating, and Loose Women.
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Terri Seymour
Extra TV host Terri Seymour, now 52, dated Simon for six years from 2002 to 2008 before they ended things because in Simon's words: "She wants a different path in life. We will be the best of mates, but I think in relationships, you have to be totally honest. I have always been and I know Terri knows that," he told Just Jared at the time.
While they broke things off romantically, Terri still remains a pivotal part of Simon's life, and seems very close to Lauren. Back when they were kids a few years ago, she regularly shared Instagram pictures of herself and Lauren enjoying playdates with Eric and her own daughter Coco, now 10, whom she raises in Los Angeles with her model and artist partner, Clark Mallon.
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Terri has previously opened up about her continuing friendship with Simon, gushing: "We do still speak every day. Actually we'll often speak to each other five, even 10 times a day. And when Simon is in LA we see each other daily." Terri still works as an entertainment correspondent for Extra TV, and this year went to her first ever Oscars red carpet alongside crossing paths with plenty of celebs at the Golden Globes.
Jackie St Clair
Former Playboy and Page 3 pin-up Jackie St Clair met Simon on the nightclub scene in the 1980s, and remained close friends after the romance ran out. While sticking close to Simon, there's no love lost between her and Sinitta, who reportedly refused to be on the boat at the same time as Jackie in 2012. Dishing on the fallout, Sinitta told the Daily Mail: "We're never in each other's company. Simon would prefer it if we could be."
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As far as Simon was concerned, he was staying well out of it. "Urrrgh! It was a pretty torrid day, absolutely hellish," he told The Mirror. "What do you think? Am I getting involved with it all? That would be a 'No!'"
According to one insider, the battle could have started over a fight to be Eric's godmother - a fight that Sinitta eventually won. Back in 2013, a source revealed to the Sunday People: 'Simon is facing a real dilemma. There are a lot of women in his life and he is still very close to all of his exes.
'But it is Sinitta and Jackie who want to be godmother to his baby. It's tricky because they really don't get on. If Simon chooses one it could be a real blow to the other. They have taken him aside and spoken about their desire to help raise the little one. They have both offered to babysit and are willing to help Lauren out when he is away working. As his closest friends they are both desperate to be involved."
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Alongside her romance with Simon, also once dated Andrew Ridgeley and Prince. Now, however, she's much more settled down. The model is married businessman Carl Michaelson, and the duo have become huge names in the London social scene, often hosting swanky events at luxury venues and hotels or posing on the red carpet together.
Mezhgan Hussainy
Before Eric came along, the closest Simon got to becoming a one-woman man came thanks to Mezhgan Hussainy. It looked like Simon had finally been tamed when he proposed to make-up artist Mezhgan on Valentine's Day 2010 in the bedroom of his plush pad in Holland Park, London.
Simon went the whole hog for the proposal, even commissioning a £250,000 six-carat engagement ring from Bond Street jewellers Graff for the occasion. Despite all of his efforts, he did an about-turn just a year later and called the engagement off - but gifted her a £5 million Beverly Hills mansion as a final parting gift.
According to Bower's biography, Mezghan had some huge distrust of Simon which led to plenty of tension, with the music man moving into a hotel in a bid to escape the bad vibes at home with his American fiancée. It seems like the tension never quite disappeared, and the makeup pro hasn't been seen with Lauren or Simon in years. In fact, she looks to have moved on completely, and went on to become the proud mum of twins Preston and Isabella in 2018 with partner Phil Miller.