Simon Cowell may have settled down over recent years but the music mogul was once quite the ladies' man. The X Factor creator, 63, is now loved-up with wife-to-be Lauren Silverman with whom he shares who shares son Eric, eight, with. The happy couple first met in Barbados in 2004, back when she was holidaying with her then-husband, real estate mogul Andrew Silverman. Years later, following Lauren's split from her husband and Simon's failed engagement to Mezhgan Hussainy, the two reconnected and begun a romance - with the pair welcoming son Eric into the world together on 14 February 2014 and the businessman popping the question on Christmas Eve 2021.
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In addition to raising young Eric, Simon is also a stepfather to Lauren's teenage son Adam Silverman from her first marriage, as the star steps into a 'semi-retirement' and enjoys the quieter life with his family.
But back in the day, the star's personal life often hit the headlines and was certainly eventful.
'Cool' threesomes
During his bachelor days, sometimes one woman in his bed wasn't enough for Simon.
Speaking in a saucy interview with US shock jock Howard Stern, Simon confessed he once found himself alone with two beautiful ladies and it turned into a threesome in the bedroom.
Discussing the ménage à trois in 2011, Simon said the encounter happened "years ago", adding: "I was just with these two girls and we ended up in bed. It was cool - I liked it."
Date with a pregnant Denise Richards
In the very same 2011 interview, Simon revealed he'd gone out on a date with Charlie Sheen’s ex-wife Denise Richards when she was eight months pregnant with the actor's baby. One-time James Bond star Denise and Charlie split in 2005 when she was pregnant with their second daughter, and Simon later revealed he'd later taken her out on a blind date during that time period. Speaking to Howard Stern, he explained she turned up with a huge baby bump. Simon said: "I did have a bizarre blind date with... Charlie Sheen’s ex.... "She’s cute. We met in a hotel and she turned up eight months pregnant with a dog in her handbag. She’s a bit of a whacko - but I like that."
Back in the day Simon seemingly mixed business with pleasure, with the businessman enjoying a brief fling with fellow X Factor judge Danni Minogue. After hiring the Australian singer on the now-defunct ITV show in 2007, Simon sparked rumors as he grew close to the mum-of-one - later going on to admit he and Danni had enjoyed a fleeting romantic union following his split from long-term girlfriend Terri Seymour. During an interview for an unauthorized biography called Sweet Revenge: The Intimate Life of Simon Cowell by journalist Tom Bower, the music mogul admitted he had a 'crush' on the star and sister to Kylie Minogue. Simon said: "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. "After Terri Seymour, I wasn’t ready for another relationship."
Dannii wasn't the only X Factor Simon was linked to over the years - with the dad-of-one once rumored to have struck up a romance with Spice Girl Melanie Brown. Between 2011 and 2016, Scary Spice served as a guest and main judge on the Australian and British versions of The X Factor, with some viewers speculating Simon was cheating on his partner Lauren with her due to their close bond. However, unlike the Dannii rumors, this fan theory turned out to be nothing more than baseless speculation - with sources close to Simon slamming the claims as "ridiculous and completely pointless".
One-time Eurovision Song Contest hopeful Katie Price may never have found her way onto the X Factor judging panel during its heyday but that didn't stop her from being linked to the show's head judge. The former glamour model allegedly spent the night in Simon's bed several years ago, revealing in 2019 how she spent the night at his London pad after an awards party back in the day. "We kissed and I ran my fingers through his chest hair," the mum-of-five recalled when discussing the past encounter.
"We were both at the Comedy Awards and I was single at the time. I’d had a lot to drink and he invited me back to his place." Multi-millionaire Simon even kindly sorted Katie a cab in the morning, however, the pair reportedly did not go all the way and have sex. Simon also once made the rather steamy confession that he'd love to have a threesome with both Katie and Britain's Got Talent's Katie Price impersonator Francine Lewis. On the ITV show, the former bachelor was asked whether he would like to date either of them and he smugly responded: "I'd have a threesome, I would."
