Simon Cowell & Lauren Silverman

Simon Cowell and Lauren Silverman’s love story is a wild ride, to say the least. Cowell, the well-known reality show judge, has reportedly started dating Lauren in 2009, five years after they met at Barbados’ Sandy Lane resort. On their first meeting, Silverman was on vacation with her then-husband Andrew Silverman. Then in 2010, Cowell was engaged to Mezhgan Hussainy, but it only lasted for a year. At first, both Simon and Lauren kept silent about their relationship until Lauren’s 2013 pregnancy forced the two to come forward about their status.

However, the pair’s bombshell announcement got overshadowed by their son Eric’s birth on February 14, 2014. Together, they bought a place to raise their son in the Upper East Side of Manhattan. Cowell already owns properties in Los Angeles, London, and Barbados, all of which he could afford, thanks to his investment in T.V. talent shows.