Simon Cowell’s relationships history

Paula Hamilton, 1976

Paula Hamilton claims she lost her virginity to Simon Cowell when she was 16, and they remained childhood sweethearts when she was growing up in Hertfordshire.

Jackie St Clair, 1970s

Simon Cowell and Jackie St Claire dated on and off during the 1970s. Like Simon Cowell and many of his exes, they have remained friends and are often seen out on the town together.

Louise Payne, 1995 – 1998

Simon Cowell is said to been engaged to former Page Three model Louise Payne. They met in 1995 shortly after Louise Payne split from Right Said Fred Drummer Fred Fairbrass.

Sinitta, 1985 to 2000 (on and off)

Sinitta and Simon Cowell engaged an on-off relationship for nearly twenty years before she had an affair with David Essex.

Alicia Douvall, 2001

Alicia Douvall and Simon Cowell dated for six months in 2001.

Georgina Law, 2000 – 2001

Simon Cowell and lap dancer Georgina Law dated for a year after he met her during a night out at Spearmint Rhino gentleman’s club.

Terri Seymour, 2002 – 2006

Terri Seymour and Simon Cowell dated for four years before their split in 2006. Following their break-up, Terri Seymour continued living in one of his Los Angeles homes for a further three years.

Jasmine Lennard, 2006

While Simon Cowell and Jasmine Lennard only had a short-lived six month affair, she has since called him the “love of her life”. During her appearance on Celebrity Big Brother in 2012, Jasmine Lennard insisted she and Simon cowell still care about each other “very much”.

Dannii Minogue, 2007

Simon Cowell and Dannii Minogue’s fling during their time together on the X Factor panel in 2007 was revealed in Tom Bower’s tell-all book last year.

Mezhgan Hussainy, 2009 – 2011

Simon Cowell met make-up artist Mezhgan Hussainy on the set of American Idol back in 2003. They began a relationship and got engaged in 2010. Their split was confirmed in February 2012 by a mutual friend Zeta Graff, who said Mezhgan Hussainy had been “too needy” for Simon Cowell.

Carmen Electra, 2012 – 2013

Simon Cowell and his X Factor fellow judge Carmen Electra were first romantically linked in late 2012, when they were seen out on several dates together. They called things off in early 2013.

Lauren Silverman, 2013

On 31st of July, 2013, it was revealed that Simon Cowell is expecting a baby with New York socialite Lauren Silverman, who is still married to real estate mogul Andrew Silverman.