Olive Penderghast (Emma Stone) envisions herself as a modern day Hester Prynne (the adulterous character from the classic English novel The Scarlet Letter) after she lies about her sexual activities on the weekend. Needled for details by her best friend Rhiannon (Alyson Michalka), the quiet wallflower eventually makes up a story about losing her virginity to a nameless college boy. In the time it takes to text or tweet, the news rips through the school and makes the previously unnoticed girl the subject of a lot of attention.
All the interest in Olive’s promiscuity seems excessive since most teen films would have viewers believe "everyone is doing it." Still she becomes the object of scorn from a group of religious fanatics at the school. Their leader is a girl (Amanda Bynes) intent on saving the sinner. (While the script condemns the idea of judging others, it does nothing to negate the negative stereotype of Christians portrayed in this film.)
Like most lies, one leads to another and soon Olive finds herself a new occupation. It may not be the oldest profession known to women, but it is close. Before long, she is approached by a number of boys, including her gay friend Brandon (Dan Byrd), who are willing to pay her to say she had intimate relationships with them, even though she hasn’t. Supposedly sleeping with a girl of her reputation will improve their own standing with their classmates and increase their chances of getting some real action.
Taking her cues from the maligned Hester who embroidered a scarlet "A" on her dresses as a sign of shame, Olive ditches her regular school clothes in favor of lacy corsets and other bedroom attire on which she sews her own red letters. Olive’s sexually liberal parents (Stan Tucci, Patricia Clarkson) don’t seem overly concerned about their daughter’s change of apparel. (While they think she dresses like a stripper, they’re happy she looks like a high-end one, the type who services men of means and status. Her mother also hopes Olive will become pregnant so that she and her husband can raise the child.)
But though Olive’s willingness to endure a besmirched character is supposedly the result of her empathy for other outcasts in her class, she eventually realizes the personal costs—both in healthy relationships with her peers (Penn Badgley) and in her standing with the adults she admires.
Despite the script’s obsession with the sexual exploits of teens, STDs and frank terms for intimacy, no overt sexual activities are portrayed on screen. Still there are some faked sexual sounds, brief unwanted attempts at kissing, the discussion of an inappropriate teacher/student relationship, cuddling between a homosexual couple and brief nudity in a nonsexual situation.
The movie also addresses a form of public humiliation that even Hester wasn’t subjected to. In the world of social networking and instant messaging, nothing remains private for long. And Olive’s inability to control the dissemination of rumors (which are highly enhanced and exaggerated with each telling) is something parents might want to address with their own children. Even Olive’s favorite teacher, Mr. Griffith (Thomas Haden Church) questions the narcissistic need of people to post every detail of life on the Internet—because, in reality, there is nothing easy about ridding one’s records of this kind of A.