BRITTNEY JONES

When: July 2010

In this instance, it's not so much about the girl involved as it was about the details of how it all went down. Accordingly to Star, the two allegedly met while bowling in an adjacent lanes at Hollywood's Lucky Strike. Ashton was with Demi and Rumor at the time, but that didn't stop him from discretely sliding Jones his number on a napkin. They began exchanging texts shortly thereafter. It wasn't Ashton pushing the action, however. Rather, it was Jones who sent the suggestive texts and coordinated the trysts.  

Smash Probability: They allegedly met up at the Kutcher residence for sex when Demi was out of town, but the actor had a strict couch-only policy, as he did not want to soil the expensive linens.