Never Been Kissed (1999)

Josie Geller, a copy editor for the Chicago Sun-Times who is 25 years old and has never been in a severe relationship, struggles with feelings of insecurity. One day, her editor-in-chief, Rigfort, gives her the assignment of reporting undercover at a high school to bring parents greater awareness of their children’s lives.

Her first day at South Glen South High School was a terrible experience for her. Josie reverts to her former nerdy persona, which was the source of all of her problems during her first year of high school. She also has an unhappy encounter with three annoying famous females named Kirsten, Gibby, and Kristin, as well as the most gorgeous and well-liked student at the school named Guy Perkins. Josie starts to lose hope, but she is encouraged when she makes friends with a nerd named Aldys, who has a good heart.

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