Simon Cowell is now the family man he always desired but the music mogul used to live a very different bachelor lifestyle.
The Britain's Got Talent judge has been the focus of plenty of rumours and confessions about his love life over the years. He turned 63 last week (October 7) but the speculation about his sex life has certainly simmered down in recent years after settling down with American socialite Lauren Silverman and their child Eric, 8.
The couple got together in 2013 and have gone from strength to strength since Simon got down on one knee in Barbados on Christmas Eve last year.
They are expected to have a dazzling wedding ceremony in London with a guest list littered with celebrity A-listers. Simon didn't hold back on expenses for the special moment and splashed the cash on a diamond ring - that reportedly set him back a jaw-dropping £250,000.
The engagement ring was clearly within the businessman's budget, having an estimated and whopping net worth of £428m.
With the X Factor creator celebrating his birthday, let's take a look at the music mogul's romantic past.
Dannii Minogue fling
Simon hired Dannii Minogue - sister of pop superstar Kylie Minogue - as a judge on X Factor when it was rumoured they had become close. It was revealed in one of Simon's biographies that he and Dannii did have a short fling together.
He 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."
Mezhgan Hussainy engagement
It is not the first time Simon has been engaged during his dating history,
Mezhgan met Simon when she was working as a makeup artist on American Idol, with Simon becoming reportedly infatuated with her. He proposed to her in 2010 but the engagement was swiftly called off in 2012.
Carmen Electra
It is reported that Simon enjoyed a fling with former Playboy model and actress Carmen Electra just as he became 'close' with fiancee Lauren.
A source told E! News: "Carmen was at Simon's house in LA when she literally busted him with Lauren. Simon called her a friend, but there was nothing platonic about what was going on if you know what I mean.
"[Carmen] high-tailed it out of there. There was no way she was going to stick around and be a third wheel."
Threesome confession
During an interview with US shock jock Howard Stern, Simon confessed that he once found himself in a room alone with two beautiful women, leading to a spontaneous threesome.
In 2011, Simon noted that the saucy encounter happened "years ago" while noting: "I was just with these two girls and we ended up in bed. It was cool - I liked it."
Katie Price
Former glamour model Katie Price claimed that she spent the night in Simon's bed at his London home following an awards party several years ago.
Katie reportedly said: "We kissed and I ran my fingers through his chest hair. 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."