Josie Geller (Drew Barrymore) is an insecure copy editor for the Chicago Sun-Times who has never had a real relationship. One day, her editor-in-chief, Rigfort (Garry Marshall) assigns her to report undercover at a high school to help parents become more aware of their children's lives.
Her first day at South Glen South High School is miserable. Josie reverts to the old geek persona that ruined her first high school career. She also has an unfortunate run-in with three obnoxious popular girls (Jordan Ladd, Jessica Alba, and Marley Shelton), and Guy Perkins (Jeremy Jordan), the school's most attractive, popular student. Josie loses hope, but is reassured when a kind-hearted nerd named Aldys (Leelee Sobieski) befriends her. Aldys, who loathes Guy and his gang, invites Josie to join The Denominators, a group of intelligent students.
Josie develops a crush on her English teacher, Sam Coulson (Michael Vartan), and becomes the top student in his class. After reciting a romantic excerpt from Shakespeare to Sam, Josie has horrible flashbacks to when she read a romantic poem aloud in class to her high school crush, a popular boy named Billy Prince (Denny Kirkwood), who later asked her to their senior prom, making her dream come true. However, on the night of the prom, Billy arrives with another girl and both of them hurl eggs and insults at Josie, humiliating her and breaking her heart.
One night while out driving with Aldys, Josie encounters Guy and his gang at a local hangout called "The Court" where promiscuity and underage drinking take place. Her managing editor Augustus "Gus" Strauss (John C. Reilly) loses patience with Josie after a rival paper scoops The Court story, and orders Josie to become friends with the popular kids. He arranges for her to wear a hidden camera, and soon the whole office becomes obsessed with her story.
Josie confides in her brother Rob (David Arquette) about her fears. Rob, who was their high school's most popular boy in his teens, urges her to let go of her old self and start anew. To help her, Rob enrolls as a student and becomes an instant hit. He then uses his influence to draw Josie into the cool crowd, much to the dismay of Aldys.
Sam and Josie grow closer, but Sam struggles with his feelings as he thinks she's a student. Guy and Josie attend the prom as Rosalind and Orlando from Shakespeare's As You Like It. Anita, Gus and Josie's other co-workers watch through the camera and are overjoyed as she is voted prom queen. As Guy dances with Aldys as an alleged act of friendship, the mean girls attempt to dump dog food over Aldys. Outraged, Josie throws her crown away and reveals her true identity. She praises Aldys for her kindness and warns the students that one's persona in high school means nothing in the real world. Sam is hurt by her lies and states he wants nothing to do with her. Also angered is Rob, who as a phony student received a second chance at baseball. Josie, ultimately making amends, secures him a coaching job.
Josie vows to give Gus a story and writes an account of her experience. In it, she admits she's never been kissed, describes the students of South Glen South, and avows her love for Sam; the entire city is moved by it. She writes she will stand in the middle of the baseball field and wait for Sam to come and kiss her. Josie waits, but the clock runs out with no sign of Sam. On the verge of giving up... cheers, then a booming roar, as Sam emerges to give her a romantic kiss.
- Drew Barrymore as Josie Geller
- David Arquette as Rob Geller
- Michael Vartan as Sam Coulson
- Leelee Sobieski as Aldys
- Molly Shannon as Anita
- John C. Reilly as Augustus "Gus" Strauss
- Jeremy Jordan as Guy Perkins
- Jessica Alba as Kirsten
- Jordan Ladd as Gibby
- Marley Shelton as Kristen
- Garry Marshall as Rigfort
- James Franco as Jason
- Denny Kirkwood as Billy Prince
- Marissa Jaret Winokur as Sheila
- Maya McLaughlin as Lara
- Giuseppe Andrews as Denominator
- Octavia Spencer as Cynthia
- Branden Williams as Tommy
- Cress Williams as George
- Sean Whalen as Merkin
- Martha Hackett as Mrs. Knox
- Jenny Bicks as Miss Haskell
- Katie Lansdale as Tracy