Life for high schooler Rick Stevens (Nat Wolff) is going all wrong. His mom tries to commit suicide and "While I'm Dead Feed the Dog" is painted on the garage door. It starts with his crush on school hottie Nina Pennington (Selena Gomez). He loses his virginity to his best friend's mom (Elisabeth Shue). His own mom (Mary-Louise Parker) appears as Saint Lola, the saint of teenage sex. He gets pushed into a bet with the mobster's son about having sex with Nina before Arbor Day. She has just broken up with her boyfriend. She likes Josh Groban and he tries to buy backstage passes from sleazy Jimmy Leach (Dylan McDermott).
This is trying to be a teen sex romp with broad satirical humor. It fails in many different ways. The first is that it fails to make Rick a likeable character. The movie needs to dump on him again and again so that he becomes sympathetic. For all the bad things that is supposed to be happening to him, the first big thing in the timeline is him having sex with his best friend's hot mom. He gets the date with the dream girl too early and too easily. He is too dislikable. Selena Gomez is completely bland as the goody girl. The movie is trying to be crude but it's trying too hard. Everything is ugly. The humor is way off. I don't know that much about director Tim Garrick and his writing partner Scott Russell. They don't have much of a track record but I did see their earlier writing effort, Jailbait. It has the same teen sex romp writing with broad satirical takes. The actors are lower grade, the production is lower, and the level of humor is similar. At least, that one's satire marginally works. None of this one works and it's a grind from the very start. I grew to hate the repeat-o-punchlines. This is wasting the talents of some pretty good actors in the adult roles. It's bad.
