Simon Cowell – 61, TV Personality

Yes, even the strict panelist of American Idol and Britain’s Got Talent is strict when it comes to marriage. Simon Cowell always goes after whatever he wants. We best remember him for his bold and brash comments from the reality competition shows we’ve mentioned. In real life, however, he is a gentleman when it comes to his long-time partner, Lauren Silverman.

While talks of wedding bells were on the news, Cowell kept mum about his future plans, which got everyone wondering if he and Silverman will step his foot on the gas and take their relationship to the next level soon. They welcomed their son Eric in February 2014, but we haven’t seen any ring on their fingers until now. Indeed, time will tell if Cowell spills even more details about his plans. He was once engaged to makeup artist Mezhgan Hussainy in 2010, but the TV personality claimed it was “a big mistake.” Maybe he isn’t ready for marriage after all.