Ben Affleck

Apart from his fame and investments, Ben Affleck has had several high-profile relationships throughout his career. However, not all of them have had happy endings. Cheyenne Rothman was one of the first women to win Ben’s heart. The couple met at a summer camp back in high school and dated for about seven years before separating in 1997. This was the time the actor rose to stardom, credits to his performance in Good Will Hunting. After, Ben was in an A-list relationship with Gwyneth, and the two dated on and off. They even appeared on screen together in Shakespeare in Love and Bounce.

His relationship with Jennifer Garner turned out to be one of his most unforgettable. The former couple had been married for over ten years and were proud parents to three children. Ben moved on, dating Lindsay Shookus and then Shauna Sexton afterward. It didn’t last as well, and in the early part of 2018, he fell in love with Ana de Armas, his Deep Water co-star, whom he met on the thriller film set in late 2019.