Dare (2009)

A drama centered around three high school seniors - an aspiring actress, her misfit best friend, and a loner - who become engaged in an intimate and complicated relationship.
When a pompous actor tells good girl Alexa (Rossum) that she hasn’t lived, she embarks on a bold journey that takes her to mysterious bad boy Johnny (Gilford). Envious, her shy best friend Ben (Springer) also dares to pursue Johnny, complicating Alexa’s romance and pushing the boundaries among the three friends.