Charlie Sheen and Denise Richards
Of course, we all know about the tumultuous relationship between Charlie Sheen and Denise Richards. Back in 1991, the two stars met, but didn’t get engaged until 2001. While Richards was pregnant with the couple’s second child, she filed for divorce due to Charlie’s drug relapse. Apparently, the two are friends now despite their history.
Ben Affleck and Jennifer Garner
Back on the set of Pearl Harbor (2001), Jennifer Garner and Ben Affleck met, and the two began dating a few years later in 2004. Together, they had three children. Unfortunately, this adorable Hollywood couple divorced in 2017. We’re still mourning.