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A Timeline Of Simon Cowell’s Dating History: Relationships, Affairs, Engagements And Hookups

Samantha Agate

Samantha Agate

Simon Cowell Relationships America's Got Talent X factor Sinitta Lauren Silverman

Simon Cowell isn’t just the king of talent competitions. He has also always been quite the ladies man. Simon has had more than a few relationships in the public eye along with several short-lived flings before settling down with his current partner and mother to his 6-year-old son Eric. Let’s take a deep dive into Simon’s relationship history and find out how he got this ladies’ man title.

Simon Cowell And Paula Hamilton (1977)

One thing that Simon Cowell did in his younger days was stand up to bullies. In 2011, model Paula Hamilton spoke about how she had a blossoming relationship with Simon when they were in primary school. Their relationship first started when Simon would ward off the bullies and mean teachers that would bother Paula when they were just 12 years old. They grew up together in Hertfordshire in the UK and when she was 16 years old, she had her first sexual experience with Simon who was also a teen at the time. She has been very open about admitting that he took her virginity. To this day, she still sings his praises and calls him very protective of her, along with being “funny and rebellious.”


Simon And Jackie Sinclair (1970s)

Jackie Sinclair is just one of Simon’s many exes that he has remained friendly with over the years. She often joins him for yacht trips with some of his other famous exes. Jackie was photographed kissing the America’s Got Talent judge in 2011 right in front of his fiancé at the time. Talk about keeping it friendly with your exes! She was one of the women that had an ongoing feud with Simon’s next ex, Sinitta. They were both vying to be the godmother of Simon’s son Eric when he was born. Sinitta eventually got that honor but there was definitely some jealousy there.

Simon And Sinitta (1984)

Simon was entranced by Sinitta, a pop star ever since they first met in the 1980s. They broke up and got back together more times than you can count on one hand. Simon even signed Sinitta to his record label in 1985 and the pair were always extremely close. She describes their relationship as a 20 year on and off-again relationship. She is yet another one of his famous exes that he has remained friends with over the years. But that came with a lot of jealousy for Sinitta who struggled when Simon was in relationships with other women. In fact, she didn’t really understand that their romantic relationship was over until Simon’s son Eric was born. She said that she will never come between family and is happy with her role as Eric’s godmother.

Simon Cowell And Louise Payne (1995)

Simon met Page 3 model Louise Payne in 1995 and was smitten. The pair had a three-year-long relationship and Simon eventually popped the question only a few weeks after they first met. But, they broke off the engagement in 1998 because Simon said he wasn’t ready to have children. He wasn’t ready to give up his bachelor lifestyle leaving Louise heartbroken.


Simon And Georgina Law (2000)

After his failed engagement, Simon had a fling with yet another Page 3 girl and lap dancer Georgina Law. She was the one that actually sold the story to the tabloids that the pair had a fling. “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,” she said. How many lap dances did it take for Simon to fall in love? That’s definitely the question on everybody’s minds. “She’s a great girl. We find an awful lot to laugh about, but she’ll never be a Pop Idol. If you’ve heard her sing in the shower you’ll know what I mean. But she has tremendous talents in other areas,” Simon said. Yeah, I think we can imagine what those other areas are.

Simon And Terri Seymour (2002)

In one of his longest relationships, it really seemed like Simon and Extra correspondent Terri Seymour would go the distance. Simon dated Terri from 2002 to 2008 and she even interviewed him numerous times before and after their split. His busy schedule was one of the reasons to blame for their split and they realized they are better off as friends. As a parting gift, Simon bought Terri a luxury Los Angeles mansion. Have you guys ever gotten such an extravagant gift after a breakup? They are still good friends and hang out together regularly. We have even seen Terri interview Simon about America’s Got Talent on the red carpet. Awkward!

“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,” she said. They hang out, have dinner together and he even threw a birthday party for her daughter Coco in 2019. Terri is also friends with Lauren Silverman and they take their kids out together to play and chat.


Simon And Jasmine Lennard (2006)

Simon Cowell and model turned reality star, Jasmine Lennard, had a rumored six-month fling in 2006. During this same time, Simon was still in a relationship with Terri Seymour. This relationship was not in the public eye and was instead kept under wraps. It wasn’t until Jasmine was cast on Celebrity Big Brother where she professed her love for Simon on live television. She felt like she disappointed Simon after being eliminated from the show, and also revealed she had his initials tattoed on her wrist.

Simon And Dannii Minogue (2007)

It didn’t take long for Simon to move on with fellow X Factor judge Dannii Minogue who he had a massive crush on immediately when he saw her in 2007. Simon later confessed that the two had a very brief love affair “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. It was genuine love” he said in an interview. It was also very short-lived as they both moved on from their fling that was only a few weeks long.

Simon And Mezghan Hussainy (2009)

Mezghan Husainy was a makeup artist on Simon’s show American Idol. He immediately saw her and found her very attractive. The pair were engaged a year later in 2010. But for Mezghan, much like Simon’s other exes, she struggled with jealousy and the fact that he was close to so many other women that he previously dated. His busy schedule jet setting all over the world was another cause of concern for her as she felt like she never got to see him. They ended their engagement in 2012 and as a parting gift, Simon bought her a multimillion-dollar mansion. Again, has anyone ever been gifted a mansion as a breakup gift? Also, it definitely seems like Simon has a knack for getting engaged but not going through with the wedding. Simon actually went on to call the relationship a “big mistake” after they argued a lot.

“I’m attracted to crazy women. I encourage crazy behavior and I make them crazy,” he said after the relationship was over. “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. My life is really odd.” It sounds like major shade directed towards Mezghan.


Simon And Carmen Electra (2012)

Actress and singer Carmen Electra dated Simon from 2012 to 2013 in a relationship we forgot even happened. They first met after Carmen was a guest just on Britain’s Got Talent. Their relationship was not as serious as Simon’s previous relationship. The relationship ended when she found Simon getting cozy with his current partner Lauren. But even still, both Simon and Carmen have nothing but nice things to say about each other. She called him “awesome and very charming.” Simon told pal Ryan Seacrest on his radio show that she is “adorable.”

Simon And Lauren Silverman (2013)

Simon has finally settled down with partner Lauren Silverman. He swooped in and romanced Lauren while she was still married to his pal Andrew in 2013. The couple divorced after news of the affair broke and Lauren announced she was pregnant with Simon’s child. The pair are now parents to 6-year-old Eric who has made several appearances on both America’s Got Talent and Britain’s Got Talent. Simon hasn’t put a ring on Lauren’s finger just yet which leads us to question if the king of talent shows will ever truly be ready to settle down and be a husband.


Do you think wedding bells are in the future for Simon and Lauren? Or is he content with being in a partnership and parenting Eric?

Let us know what you feel about this article

About the Author

Samantha Agate

Samantha Agate is the Talent Guru here at Talent Recap. Her work has been featured at The Blast. Samantha graduated from Hunter College in 2019 with a degree in Media Studies and a Concentration in Journalism. When she isn't binge-watching reality television shows or binge-eating fried food, she loves hanging out with her friends and family and petting puppies.

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