Simon Cowell

Simon Cowell » Dating History


Simon Cowell Dating History

Historical look at Simon Cowell relationships, listed in date order.
  •  Profile
  •  Married
  •  Relationship
  •  "Encounter"
  •  On-Screen

Paula Hamilton
Paula Hamilton and Simon Cowell unknown date
"Paula’s happiest memory is, apparently, of her first love — Simon Cowell. She went to the Licensed Victuallers’ School in Slough with him and his brother Nicholas, and lost her v*rginity to Simon when she was 16. ‘I’ve made a lot of mistakes in my life, but Simon w ... [more]
Jackie St Claire
Simon Cowell and Jackie St Claire unknown date
Cowell, 49, has famously kept his enemies close, and his ex-girlfriends Sinitta and Jackie closer. Jackie is known for the dubious honour of being a former Miss Nude UK and Page 3 girl. And she often accompanies Cowell on his winter break to Barbados. While Cowell admits that as a boyfriend he leaves ... [more]
Danielle Delaney
Danielle Delaney and Simon Cowell unknown date RUMOR
According to extracts from Tom Bower's The Intimate Life of Simon Cowell published in the Sunday Mirror newspaper, the X Factor mogul enjoyed a string of dates with actress Danielle Delaney. A friend said: 'She was desperate for the relationship to become more serious, and still is. To her ... [more]
Sinitta Renet Malone
Simon Cowell and Sinitta Cowell 1984
"Probably Simon's most famous ex, Sinitta dumped him when she embarked on an affair with David Essex. They're still mates though (standard) and she's even wrangled herself some regular guest-mentoring gigs on X Factor. [more]
Georgina Law
Georgina Law and Simon Cowell 2001 RUMOR
"Page 3 girl and lap dancer Georgina sold a kiss and tell story about her relationship with Simon with Simon's blessing. 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 ... [more]
Alicia Douvall
Alicia Douvall and Simon Cowell 2001
In an interview, Simon stated that "Yes I`m afraid we did sleep together, me and Alicia," he admits a little glumly. Former glamour model Alicia Douvall has stepped forward to reveal she had a six month affair with music mogul Simon Cowell - and once ended up having sex with him 11 times in ... [more]
Deborah Corrigan
Deborah Corrigan and Simon Cowell June 2001
"POP Idol supremo Simon Cowell has been branded a FLOP IDOL in bed by his ex-lover Debbie Corrigan. Stunning glamour model Debbie, former girlfriend of comedian Jim Davidson, was left unimpressed by Mr Nasty's performance between the sheets. Week after week Cowell, 42, sits on the ITV talent ... [more]
Terri Seymour
Simon Cowell and Terri Seymour 2002 - 2006
On an early episode of MTV Cribs, Simon introduced Terri as his cook. Well, since then the world has seen that in fact she’s the other half of the acid-tongued reality TV judge. [more]
Jasmine Lennard
Jasmine Lennard and Simon Cowell 2006
The two were first seen together back in 2006. Jasmine was seeing night club owner Mark Alexiou while Cowell was seeing Terri Seymour. The two denied the allegations claiming the were very good friends. Cowell claimed Jasmine was asking him for career advice. Speculations of their relationship rose ... [more]
Dannii Minogue
Simon Cowell and Dannii Minogue 2007 RUMOR
"The revelation that Simon was sleeping with Dannii while she was an X Factor judge was revealed in Tom Bower's unauthorised biography of Cowell called 'Sweet Revenge: The Intimate Life of Simon Cowell'. In it Simon says, "It was Dannii's hair, the sexy clothes, and the t**s ... [more]
Lauren Silverman
Simon Cowell and Lauren Silverman 2009
as of July 31, 2013.. they broke up and got back together in August 2013. It's true. Simon Cowell is finally going to be a dad! The X Factor judge, 53, is expecting his first child with New York socialite Lauren Silverman, 36, multiple sources confirm to PEOPLE. The news has been hot gossip among ... [more]
Mezhgan Hussainy
Mezhgan Hussainy and Simon Cowell August 2010 - 2012
Carmen Electra
Simon Cowell and Carmen Electra December 2012 - February 2013 RUMOR
Carmen Electra briefly dated Simon Cowell earlier this year and remains close with The X Factor judge, so she has more insight than most on what kind of father he will be. Her prediction? "As the person that I had the chance to see ... a very kind, sweet, funny person who really stands for the ... [more]

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