George Clooney and Talia Balsam

While he might have been known as one of Hollywood’s biggest bachelors before his current marriage, that wasn’t always the case. Back in 1989, he married actress Talia Balsam. However, it was clearly something not meant to last. The pair filed for separation just 25 months after standing in the alter.

Afterward, Clooney would go on to become, arguably, Tinseltown’s biggest free catch, until human rights lawyer Amal Clooney married him in 2014. Meanwhile, Balam also married another star: actor John Slattery, from Mad Men!