We all know Simon Cowell as the cranky judge from American Idol, but the music producer has been in relationships with many famous women throughout the years. Despite his harsh on-screen persona, he must have a certain amount of charm, though he has yet to truly settle down with one woman.
From the beginning of his career in the 1970s to now, Simon's love life has been complicated and dramatic. His off-and-on relationships and friendships with exes have kept him from marrying, but a marriage could be on the horizon soon if his latest match proves to be "the one."
The first of Simon's many beautiful ex-girlfriends, Jackie, was a Page 3 model who dated Simon in the 1970s. While the details of their relationship remain somewhat private, the two have remained close friends over the years. Jackie and singer Sinitta, Simon's longest off-and-on girlfriend, had a long-standing feud over him. She was also photographed kissing him on the lips in front of his ex-fiancée in 2011. Simon and singer Sinitta met in the 1980s and officially started dating in 1984. They've had a long, tumultuous relationship ever since. Sinitta revealed that, before Simon's son was born in 2014, she was never sure that the relationship was really over. Simon and Sinitta also remain close friends, and she is the godmother of his son, Eric. Their 20-year off-and-on relationship was unsuccessful because Simon kept in close contact with other women he had dated.
Another Page 3 model caught Simon's attention next. He and Louise Payne started dating in 1995 and had a three-year relationship. Simon was so smitten with Louise that he asked her to marry him only a few weeks into their relationship. However, they never tied the knot and broke up because Simon wasn't ready to have a family yet. Simon then started dating Extra correspondent Terri Seymour in 2002, and it became one of his longest and most serious relationships. The two broke up six years later in 2008 when they decided they should just be friends. Simon's busy schedule was one of the main reasons behind their split, and he felt so bad about it that he bought Terri a mansion in Los Angeles as a breakup gift. The two are still friends, and Terri is good friends with Simon's current girlfriend, Lauren Silverman.
Mezghan and Simon met during filming for American Idol in 2009. Mezghan was Simon's makeup artist, and he was instantly attracted to her. The two had an intense three-year relationship and got engaged in 2010. They called off the engagement in 2012 because of jealousy and Simon's busy schedule. Simon also gifted Mezghan a multi-million dollar mansion when they broke up, but later called her crazy. After a short-lived relationship with star Carmen Electra, Simon was rumored to be dating Lauren Silverman, then-wife of his friend, Andrew Silverman. Andrew filed for divorce in 2013, and news broke that it was because Lauren and Simon were having an affair. Lauren announced soon after that she was pregnant, and she and Simon welcomed their first child, Eric, in 2014. Despite the dramatic beginning of the relationship, Lauren and Simon have been together ever since. Perhaps a wedding is in the cards for him after all!
Source: Simon Cowell