In a February 2017 feature at The Ringer that interviewed Amy Heckerling and wrote about her entire career, Heckerling said that the main reason this film failed is that the studio insisted it be delivered as a PG-13 film even though it was intended by everyone else, from Heckerling to the since-departed studio executives who'd greenlit production, as an R-rated comedy. The studio said that R-rated comedies weren't welcomed by enough audiences and forced the film to be watered down considerably. Heckerling said the movie failed because audiences could tell it was not doing what it was intended to do.
The scene featuring David Spade was filmed in Toronto's first specialty video store Revue Video. Since the store specializes in films (Foreign Language and Classics) other than the ones feature in the scene, the whole look of the store had to be changed.
The character of Dora Diamond is in part inspired by Franz Kafka's girlfriend late in his life, Dora Dymant. Kafka is mentioned in the English class scene in the movie.
The music video of the song "Teenage Dirtbag" by Wheatus features the characters of this film, as the song features on the movie's soundtrack. Unlike the movie, the music video is set at a high school and Dora dates a bully jock and not a sleazy college professor.
During the scene where Paul sits at the fountain in the quad, the song Scarborough Fair by Simon and Garfunkel is playing. This scene is an homage to El graduado (1967). Jason Biggs actually played the main role of Benjamin Braddock in a Broadway run of 'The Graduate'