Teenager Rick Stevens (Nat Wolff), has a crush on Nina Pennington (Selena Gomez). He makes his move when he realizes she broke up with her boyfriend Kevin Carpenter. To win Nina over, Rick places a bet with Karlis Malinauskas, a mobster's son, that he will have sex with Nina before Arbor Day, leading to a chain of events involving his best friend's mom and almost the whole town in jail, including Nina.