As one of Hollywood’s hottest leading men, Tom Cruise knows that finding love can be a risky business.

Cruise has been married three times: to Mimi Rogers from 1987 to 1990, to Nicole Kidman from 1990 to 2001 and to Katie Holmes from 2006 to 2012. He has also romanced Cher, Heather Locklear and more A-listers.

As his career continued to skyrocket, Cruise’s splits gained more attention. However, the actor is notorious for keeping the reasons behind his breakups private.

“She knows why, and I know why,” Cruise told Vanity Fair in October 2001 of his and Kidman’s divorce. “I think that you just move on. And I don’t say that lightly. I don’t say that with anything. Things happen in life, and you do everything you can, and in every possible way, and there’s a point at which you just sometimes have to face the brutal reality.”

Scroll down for a closer look at Cruise’s most famous relationships and flings: