Teenager Rick Stevens (Nat Wolff), has a crush on Nina Pennington (Selena Gomez). When Rick realises that Nina broke up with her boyfriend Kevin Carpenter (Austin Stowell), 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.<ref name="Hollywood Reporter"></ref>