For most of his career, Simon Cowell was a proud bachelor until he started dating his fiancée Lauren Silverman.
Simon, 62, and 44-year-old Lauren, who is also the mother of his seven-year-old son Eric, announced they would be getting married after Cowell proposed to them in January this year.
Although it seems that Simon has died this time to get married, confessing that he is tired of married life, it is not the first time he plays with the idea of calming down.
Throughout his dating history, Simon has proposed to more than one woman, but quickly canceled the engagement.
Before becoming a father, Simon was also known for sailing on the high seas on a luxury yacht with a group of beautiful women.
Let's take a look back at Simon Cowell's love life as he gets ready to finalize his status as a married man and look at all the ups and downs of his decades-old dating history, rtv21.tv reports.
Simon had an affair with former model Jackie St Clair in the ’70s and since their split the pair have remained strong friends.
Reports have circulated that the 61-year-old is currently involved in an ongoing quarrel with another ex-lover of Simon - Sinitta.
Both Simon and Sinitta have had an ongoing relationship for over 30 years, starting in the 80s.
In one case, the pop sensation said that her romance with the judge "was never over" and that they have maintained a strong friendship, even Sinitta has been called Eric's godmother.
Another model in Simon's love life, Louise met the talent judge for three years. In fact, he was so struck by her that he asked for her hand in marriage after just a few weeks.
Despite this, the couple never married and eventually separated, with reports suggesting that Simon was not ready to have a family at the time.
Simon began his long relationship with Extra Terri Seymour correspondent in 2002.
Six years later, the couple split in 2008 and decided to remain friends with reports suggesting that Simon's extremely busy work schedule had a role to play in ending the relationship.
Simon was known for accompanying around a gang of beautiful women, most of whom were his ex-girlfriends, whom he would send for luxury vacations in Barbados.
He could be seen regularly walking on the beach surrounded by girls dressed in bikinis, which dispelled a whirlwind of rumors of what the group got up to when it hid from the public eye.
In 2013, Sinitta sparked rumors with a secret Twitter post that simply said, “Harem. "- A group of women held together to have sex with a man."
But later she insisted that things were strictly platonic.
"We are not all sleeping with him. It's bad enough to call us his b ****. "The girls are all there with partners or as friends," she said.21Media