When: 2001-2002

Shortly after splitting with January Jones, Ashton jumped into a nine-month relationship with Dark Angel actress Ashley Scott. Although she had a lucrative TV gig, Ashton seemed to have loftier goals and was looking to make a high-profile upgrade to a big-screen starlet. In the end, Ashton and Ashley were in different places in their respective careers. Ashton had both successful TV and movie ventures and Punk'd was on the horizon, while Scott's career prospects weren't nearly as promising. The writing was on the wall.

Smash Probability: At the time, the world was Ashton's oyster and he took what he wanted.

Also Watch