Olive Penderghast (Stone) is a normal high-school student who doesn’t exactly stand out in a crowd. When she lies to her best friend about sleeping with a college guy one weekend, this is overheard by Marianne (Bynes), the school’s religious fanatic, and word soon spreads all over school about her sexual exploits. Everything changes for Olive – she’s now the most talked about student in school. She then helps out a gay friend by pretending to sleep with him and this is when her world starts to truly get out of control, as more boys approach her for ‘help’. Olive chooses to bask in this attention and sees her life paralleling the book The Scarlet Letter, which she’s currently studying. However, when she realises she’s also possibly the loneliest girl in school, she sees a downside to this whole situation and has to do something about it. And does this also mean that she no longer has a chance with Todd (Badgley), the nice boy she’s had a crush on for years?