Never Been Kissed

Josie Geller is an insecure 25-year-old copy editor for the Chicago Sun-Times who has never had a real relationship. One day, her editor-in-chief, Rigfort, 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, Kirsten, Gibby and Kristin, and the school's most attractive and popular student, Guy Perkins. Josie loses hope but is reassured when a kind-hearted nerd named Aldys 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, 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, 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 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 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. The movie ends with Sam telling her though it took him a long time to get where he is, he finally is here and then they kiss again.

Song appearances

• During the scene where Josie and Aldys are talking to each other on the football field, the band plays the theme song from The Simpsons.
• During a scene where Josie is remembering her bullying in high school, Cyndi Lauper's "She Bop" is played.
• "(I Just) Died in Your Arms" by Cutting Crew plays when Josie first sees Guy entering the classroom.
• American ska band Spring Heeled Jack U.S.A. submitted a song named "Josie" for the film's soundtrack. The band had previously released a single titled "Jolene" which was about their tour van, but when given the opportunity to submit a song for the soundtrack, they simply replaced the name Jolene with Josie to make it relevant to Barrymore's character in the film. It was later rejected.
• The morning after Josie's experience with marijuana, "Me Myself and I" by De La Soul is heard playing.
• When Josie is remembering her first senior prom, Madonna's song "Like a Prayer" can be heard in the background.
• The single "Lucky Denver Mint" by Jimmy Eat World is featured in the film's soundtrack, and was the only single from their album Clarity to consequently gain airplay on popular American radio.
• A significant amount of the song "Heaven Tonight" by Hole appears in the film.
• The Latin funk band Ozomatli makes a cameo.
• During the climax, in the scene when Josie receives her first kiss from Sam on the baseball field, the song "Don't Worry Baby" by The Beach Boys is played.
• While Josie and Sam are dancing, the song "Please, Please, Please, Let Me Get What I Want" by The Smiths can be heard in the background.
• The song "Erase/Rewind" by The Cardigans is played, in the background, towards the end of the movie, at the prom night when the prom king and queen dance.
• The song "Watching the Wheels" by John Lennon appears in the movie.
• Kottonmouth Kings' "Suburban Life" plays when Josie pulls up to the school and her car backfires.
• The song "Peppyrock" by BTK is featured in the movie.

• South Glen High School was filmed at John Burroughs Middle School located in the Hancock Park area of Los Angeles at 600 South McCadden Place
• Josie's childhood home is located at 368 North Ridgewood Place in the Hancock Park area of Los Angeles.
• Nana's coffee shop where Josie and Aldys have lunch is the Monrovia Coffee Company located at 425 South Myrtle Avenue in Monrovia, CA.
• The Tiki Post where Rob worked is now a Cold Stone Creamery located at 408 South Myrtle Avenue in Monrovia, Ca.
• The exterior scenes for the prom were filmed at 4526 Wilshire Boulevard in Los Angeles, CA. The interiors were filmed at the Ebell located at 743 South Lucerne Boulevard in Los Angeles, CA.
• Josie's office and job scenes were filmed in Chicago and readers of the Chicago Sun-Times were filmed on the Chicago Avenue stop on the CTA Brown Line.
• Jackie Robinson Stadium was the location used[2][3][4] for the climatic scene[5][6] in which Josie waits for her first real kiss from Sam.

The film is recognized by American Film Institute in these lists:

• 2002: AFI's 100 Years...100 Passions – Nominated[19]

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