In keeping with its connection to Nathaniel Hawthorne's The Scarlet Letter, the film thumbs its nose at hypocrisy and those who stand in judgment of others. Though it sometimes goes about this noble goal in a ham-handed way -- i.e. by stereotyping certain groups (like Christians and high schoolers in general) -- it does confront important questions about labeling and judging others (especially when your own life isn't perfect).
A teen slaps a peer; another gets into a fight, though viewers don't see the actual skirmish -- just him nursing a bleeding nose. A guy gets pushy trying to kiss a girl.
Though viewers don't actually see anyone having sex, the characters talk about it a lot, and the subject permeates the whole movie. Virginity (and the loss thereof) is a frequent topic of discussion. High schoolers gossip about a classmate's sex life. A girl and a boy fake having sex behind closed doors by making very loud grunting sounds and talking "dirty" to each other. A main character wears suggestive clothing to confront her "easy" reputation. A teacher talks about having sex with a student (who's of age). A quick glimpse of the side of a breast (the woman's a nudist). There's a vibrator in the movie, though it's not seen (wrapped in paper). Mention of a sexually transmitted disease.
Language includes several uses of "s--t," plus "ass," "hell," "damn," "screw," "tw-t," "skank," "d--k," "t-t," and "whore." Also "goddamn" and "oh my God."
Lots of logos/mentions of stores/brands, including Costco, Home Depot, Target, Quiznos, T.J. Maxx, Bath & Body Works, and other mall-type stores (most are in the context of gift cards that the main character takes as payment for doing reptuation-related "favors" for guys).
Drinking, Drugs & Smoking
A bong is shown briefly. A teen asks another if he can fetch her a drink at a party (though viewers don't see them imbibing).