Ashton Kutcher and Demi Moore (2005-2011)
Ashton Kutcher began dating Demi Moore, who is 15 years his senior, in 2003. The adorable twosome tied the knot on September 24, 2005, in a small Kabbalah-oriented ceremony. It seemed like a match made in Hollywood heaven: They flirted on Twitter, and they even founded an organization dedicated to fighting the global sex trade.
But when Ashton slept with 22-year-old nobody Sara Leal on the couple's sixth wedding anniversary in September 2011 (allegedly just one of many infidelities), @MrsKutcher reconsidered their relationship. She filed for divorce on November 17, 2011.