14. Sean Penn & Leila George

Sean Penn rose to a widespread degree of fame back in 1980s. Since then, fans of the multi-Academy Award winner have seen him go through several romantic relationships throughout his career. He was married to the pop queen herself, Madonna, in the late-1980s and to fellow Hollywood-heavyweight Robin Wright from 1996 to 2010. Just recently, he married American-Australian actress Leila George in 2020.

Disregarding the big age difference, they might just be meant for one another. After all, it took Penn several years for the actor to win George’s heart over before they eventually tied the knot. According to PEOPLE, the couple has been romantically linked since 2016 and were in an on-and-off relationship for the years that followed. Eventually, Penn realized that she might be the one and had to work hard to win her over again. They had a small intimate wedding and currently enjoy the privacy of their relationship, making rare public appearances together.