Never Been Kissed - Plot

Plot

Josie Geller (Drew Barrymore) is a copy editor for the Chicago Sun-Times who has never had a real relationship. One day during a staff meeting, the tyrannical 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.

Josie tells her brother Rob (David Arquette) about the assignment, and he reminds her that during high school she was a misfit labelled "Josie Grossie", a nickname which continues to haunt her.

Her first day at South Glen South High School is miserable. Josie reverts to the old geek that ruined her first high school career. She also has an unfortunate run-in with Gibby, Kirsten, and Kristen (Jordan Ladd, Jessica Alba, and Marley Shelton), three mean, popular girls, and Guy Perkins (Jeremy Jordan), the most attractive, popular student at South Glen South. Upon discovering that Guy and his friends have hidden her car, Josie loses hope, but is warmed when a kind-hearted, intelligent girl named Aldys (Leelee Sobieski) befriends her. Aldys dislikes Guy and his gang, referring to them as "lemmings", and they in turn view her as an uncool geek. Aldys suggests that Josie should join The Denominators, a group of intelligent students. Josie does but fails to get her story.

Josie becomes enamoured with her English teacher, Sam Coulson (Michael Vartan), who is a fan of Shakespeare, as is Josie, and she becomes the top student in his class. After reciting a romantic excerpt from Shakespeare to Sam, Josie has horrible flashbacks to where she read a romantic poem aloud in class to her high school crush, a popular boy named Billy Prince (Denny Kirkwood), who made fun of her for it.

One night while out driving with Aldys, Josie encounters Guy Perkins and his gang at a local hangout called "The Court" where promiscuity and underage drinking takes place. Guy is nasty to Josie and Aldys, who claims that nothing exciting happens in Guy's court, but Josie knows from experience that Aldys secretly longs to be popular. Her superior Augustus "Gus" Strauss (John C. Reilly) loses patience with Josie after a rival paper exposes the truth on The Court, and orders Josie to become friends with the popular kids. He arranges for her to wear a hidden camera that will report back information to Gus, and soon the whole office becomes obsessed with Josie's story. Josie's co-worker Anita (Molly Shannon), after hearing Josie's recital of Shakespeare, grows unhappy with her promiscuous lifestyle and develops an attraction towards Gus, and he reciprocates.

Josie goes home and confides in Rob about her fears. She tearfully tells him that South Glen South is simply a repetition of her old high school days and all she wants is to be accepted and not abused. Rob - who was the most popular guy in school in his youth - insists that if Josie can get one cool person to like her, then no one will dare question her. He urges her to let go of her old self and start anew. Determined, Josie goes to school the next day and overhears Guy telling his group about a cool band that are playing in a bar that night. Josie follows and meets Sam and his uptight girlfriend, Lara (Maya McLaughlin). However, she is tricked into eating a hash brownie and makes a fool of herself onstage by dancing wildly in front of Guy, the girls, and Sam.

The next day, Josie oversleeps and is late for school. As her hand was stamped "loser" the night before at the club, the ink prints the word "loser" on her forehead, unknown to her. She merrily goes to school and is horrified to find everyone mocking her. She runs to the bathroom, sees the mark on her face and vomits in the toilet. She breaks down in tears and remembers the night of her prom. She was overjoyed at the thought of Billy Prince taking her to the prom and waits outside for him in her prom gown. But when Billy arrives in his limo, he has another girl with him and the both of them hurl eggs and insults at Josie, who collapses in tears. As she runs through the school hall, she encounters Rob who has enrolled as a new student and schemes to help her be popular. He becomes an instant hit with Guy Perkins and the other trendy kids, and spreads incredible stories about Josie, convincing the others that she is not a loser. Much to the anger of Aldys, Josie becomes popular and hangs out with the cool crowd.

Sam and Josie grow closer but Sam struggles with his feelings as he thinks that she is a student and therefore off limits. Josie begins dating Guy and she recommends that the theme for the senior prom should be "Meant for Each Other", famous couples throughout history. This idea is met with approval and Guy and Josie attend the prom as Rosalind and Orlando from Shakespeare's As You Like It. Anita, Gus and Josie's various 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, Josie dances with Sam and watches, horrified, as Gibby, Kirsten and Kristen nearly pour dog food over Aldys as revenge for her insulting them. Josie knocks the can away from Aldys and spills dog food over the three girls, who turn on her and denounce her as a loser. Infuriated, Josie throws her crown away and reveals her true age and occupation, and that she is disgusted by them. She angrily states how shallow the popular girls are, and praises Aldys for her kindness. Josie warns the students that who one was in high school means nothing outside in the real world and urges them to be themselves. She flees and leaves the students appalled. Sam is hurt by her lies and states he wants nothing to do with her. Also angry is Rob, who as a phony student received a second chance to play baseball and be scouted for the pros. He tells Josie that he "taught those kids something" and that she totally ruined things for him and the team.

Josie vows to give Gus a story and write her story of her own high school career. She admits she has never been kissed, and also mentions the students of South Glen South, kindly remarking on Guy's confidence, Gibby, Kirsten and Kristen's beauty, and Aldys's intelligence, and her love for Sam. The entire city is moved by her story and the pain she suffered in her teens. She says she will stand in the middle of the baseball field and wait for Sam to come and kiss her, if he really loves her. She also makes amends with Rob by using her influence at the paper to secure Rob an assistant coaching job with the team, something he proves to be successful doing. Josie waits but Sam has not heard as he is moving to New York. She waits with encouragement from Anita, Aldys, Gus, Guy and the girls.

The clock runs out with no sign of Sam. A heartbroken Josie drops the microphone she's been holding to the ground. Fighting tears, she hears cheers rising from the bleachers seconds later as Sam rushes to the pitcher's mound. Sam apologizes for being late and kisses Josie for the very first time.