Never Been Kissed

Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew Barrymores production company, Flower Films, directed by Raja Gosnell and starring Drew Barrymore, David Arquette, Michael Vartan, Leelee Sobieski, Jeremy Jordan, Molly Shannon, Garry Marshall, John C. Reilly, and James Franco in his film debut.

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 runin with three obnoxious popular girls Jordan Ladd, Jessica Alba, and Marley Shelton, and Guy Perkins Jeremy Jordan, the schools most attractive, popular student. Josie loses hope, but is reassured when a kindhearted 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. ........

Source: Wikipedia