Wilmer wouldn't let go of his affinity for tough-girl rock stars. In 2009, he hooked up with angsty songbird Avril Lavigne. While their relationship would prove to be another brief fling (imagine that!), they seemed to have some fun together while it lasted. In November, the duo was spotted at clubs across Los Angeles, including Wonderland. A spy told People magazine at the time that they were cozy all night, arriving together, rubbing on each other and leaving together. "Avril had her hand on his knee at one point," a source told People. "They looked super cozy together." Not cozy enough to stay together long, though, which is understandable considering that Avril was fresh from a divorce filing the month prior. That, and Wilmer's wandering eye, of course.