When: 2002-2003

They started dating in late 2002 after filming Just Married. However, their fling ended abruptly after seven months, to the surprise of Ashton and Brittany's friends and family. "He likes going out all of the time, and she's more of a homebody," a source close to the situation later explained. Nevertheless, the two remained friends up until the actress' untimely death in December 2009. Upon hearing the news of Murphy's passing, @aplusk took to Twitter: "2day the world lost a little piece of sunshine. My deepest condolences go out 2 Brittany’s family, her husband, & her amazing mother Sharon." He concluded with, "see you on the other side kid." 

Smash Probability: During an MTV interview to promote Just Married, Murphy revealed the key to a lasting romance, saying, "I mean, to have a healthy sexual relationship with your partner, I think that's important." We are willing to bet she practiced what she preached with her co-star.