A man and a woman go out on a “big” third date. He’s ashamed to admit he just lost his job, and she’s afraid he’ll run away if he finds out that she has a kid. Small lies lead to bigger ones and the night gets crazy very soon.

High school senior Bobby Chrystal fails his French class, which will block him from entering Yale. His rich, authoritarian father hires an attractive 29-year-old to tutor Bobby over the summer and help him pass a make-up exam. While Bobby’s friends lead him away into strange excursions aimed at losing their virginity, Bobby finds all the extracurricular activities he needs with his new tutor.