#24: Jennifer Lopez and Casper Smart

Before coming back to her ex-boyfriend, Ben Affleck, JLo didn’t mind dabbling with the idea of dating someone significantly younger than her. To be fair, when you look like the way she does, it only makes sense that you are likely to attract other good-looking people, who are probably going to be much younger.

In 2011, just after her split from Marc Anthony, JLo began dating backup dancer, Casper Smart. Despite having an age difference of 18 years, the couple was together for two and a half years. However, their split ultimately lead her to marry and divorce Alex Rodriguez and finally find her way back to her long-time love, Ben Affleck.