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American teen comedy starring Nat Wolff and Selena Gomez. Rick (Wolff)'s friends think that Nina Pennington (Gomez) is way out of his league, but Rick is confident he can win her over. He enters into a bet with his friends that he can lose his virginity to her, but he must overcome a number of hurdles in his quest including a horny housewife, a drug-abusing boss and a perverted school principal. The supporting cast includes Heather Graham, Mary-Louise Parker, Jason Lee and Gary Busey.
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