It stars Nat Wolff and Selena Gomez alongside Mary-Louise Parker, Elisabeth Shue, Heather Graham, Jason Lee, Dylan McDermott and Cary Elwes.

[2] Teenager Rick Stevens (Nat Wolff), has a crush on Nina Pennington (Selena Gomez).

When Rick realizes that Nina broke up with her boyfriend Kevin Carpenter (Austin Stowell) he makes his move.

He places a bet with Karlis Malinauskas (Nate Hartley), a mobster's son, that he will have sex with Nina before Arbor Day, leading to a serious chain of events from having sex with his best friend's mom (Elisabeth Shue), to having almost the whole town in jail, including Nina.

Principal photography took place at John Burroughs Middle School in Los Angeles, California in August 2012.