Bianca (Larisa Oleynik) is the school's most recognized sweetheart, but in fact, she has never had a date - Bianca's father is extremely strict with his daughter, and boys can only stay away from her. Under his daughter's constant protest, the father finally made a "concession" and stated that Bianca could go on a date as long as her sister Kate (Julia Stiles) also went. Hearing this news, Cameron (Joseph Gordon-Levitt), who has a crush on Bianca, is determined to find someone who can date Kate no matter what. After carefully selecting, he found Patrick (Heath Ledger) to help. Kate is a monster in everyone's eyes. It seems that she is cynical and has a feeling of dissatisfaction with everyone and everything. To make the date go smoothly, is this an unprecedented challenge or an impossible task?