With his divorce from Jennifer Lopez making headlines, we take a look back and what could have been with some of his other exes. The high school sweethearts went to Cambridge Rindge and Latin High School in Cambridge, Massachusetts and stayed together for almost seven years. You can see how their similar interest in film helped Cheyenne and Ben stay together for so long because as Ben went off to be an A-list actor, Cheyenne had a brief stint as a film director, directing Release the Cracken in Ben Affleck and Gwyneth Paltrow found each other quite quickly after his split from Cheyenne in and her split from Brad Pitt.
The two actors went on to star in Bounce and Shakespeare in Love after they began dating and their relationship lasted for three years, however, the pair were on and off again throughout that time. I think they were OK with the two of us not being together. But 17 years later, the unimaginable happened, after marriage, kids, a divorce and some shorter-term relationships, it looked like like Ben felt Jennifer was the one that got away and in he began sending her love letters.
In , a decade after they originally planned to wed, the two finally got married in Vegas and then organised a bigger ceremony for their extended friends and family. But unfortunately, the pair just aren't meant to be and by August of , split rumours had been rife for a year and Jennifer filed for divorce. After his first break up with Jennifer Lopez, Ben moved on quickly to yet another co-star having met Jennifer Garner whilst working together on Pearl Habour in and Daredevil in The pair got married just a year after dating in and stayed together for over a decade, bringing three children into the world, Violet, Seraphina and Samuel.
The couple reportedly split because they had grown apart and the years of couple's therapy just wasn't enough. Regardless of why it ended, the pair managed to stay good friends and co-parents to their children. Deviating away from the on-screen stars and taking a little time for himself after his public break up, Ben began dating Saturday Night Live producer Lindsay Shookus two years after his marriage ended and one year before his divorce was finalised.
With Lindsay used to working behind the cameras with big stars, the pair seemed like a good match. Unfortunately by , things had begun to fall apart and reportedly the relationship ended because the pair struggled with their busy lives and schedules. After a reported fling with Playboy model Shauna Sexton in , Ben settled into a relationship with actress and Bond girl Ana de Armas.
