Christine (Cates), a student at an exclusive all-girls private school, is in love with Jim (Modine), who attends an academy for boys nearby. This attracts the attention of Christine's arch-rival Jordan (Russell), who is willing to do whatever it takes to break them apart. A subplot involes Jim and his uber-slob buddy Bubba (Michael Zorek) engaging in sexually-minded practical jokes, while Bubba tries to score with Jordan himself even as he goes out with Christine's cynical friend Betsy (Kathleen Wilhoite).
This film features examples of:
- Auto Erotica: Headmistress Miss Dutchbok mistakes the chauffeur of Jordan's father, Chauncey, for Jordan's father, and has sex with him in the back of his car. Bubba and Betsy then climb into the front seat and turn on the loudspeakers, ensuring that the chauffeur and Ms. Dutchbok's indiscretion are known by everyone present.
- Beta Couple: Jim's best friend, Bubba, and Chris's best friend, Betsy, form a secondary couple.
- Boarding School: Both Chris and Jim attend single-gender boarding schools, Cherryvale (all-girls) and Freemount (all-boys), respectively. Most of the antics of the film involve Jim and his friends trying to sneak into Cherryvale.
- The Cameo: Sylvia Kristel (who knows a thing or two about sex escapades) appears as Ms. Regina Copoletta, the school's sex education teacher, while Martin Mull turns up as the pharmacist who Jim attempts to buy condoms from.
- Disguised in Drag: Jim, Bubba, and another friend dress as women to sneak into the girls' dorm. It's apparently very effective, although when Jim later confesses it to Jordan, she says that she knew already.
- Getting Hot in Here: Jordan does this to herself — deliberately turning up the heat to give her an excuse to disrobe as part of her plan to try to seduce Jim.
- I Need to Go Iron My Dog: Done by, oddly enough, the arcade machine that Jim plays at one point.Arcade Voice: [playing "The Big Score" game] Hey, big boy. Think you're man enough to score with me?
Jim Green: I am, if Bubba is.
Arcade Voice: Oops, sorry, tonight I gotta wash my hair.
- Making Love in All the Wrong Places: This being a teen sex comedy, this is a given. Bubba and Betsy at one point sneak off to the headmistress' office to have sex, but the two are caught in the act by the headmistress and her friends. Later on, they give it another go on the car of Jordan's father, only to accidentally catch the chauffeur and Ms. Dutchbok.
- Moment Killer: Chris and Jim find several of their attempts to have Their First Time foiled by these. (The concept of a door with locks on them seems foreign to characters in films like this.) They finally succeed at the beach near the end.
- Mooning: The film ends with the graduating girls of Chris's school mooning Headmistress, Miss Dutchbok.
- Ms. Fanservice: We get numerous scenes of female characters (particularly Jordan) in various states of undress.
- Pastel-Chalked Freeze Frame: The film does this in the opening, showing various scenes from later in the film drawn in this style. It's also how the movie ends.
- Their First Time: The premise of the film concerns Chris telling Jim she wants to surrender her virginity to him, and after that, almost all the humor involving them in the movie is having several of their attempts to do it foiled. (The concept of a door with locks on them seems foreign to characters in films like this.) They finally succeed at the beach near the end.
- Vanity License Plate: The car of Jordan's father Mr. Leigh-Jensen has one that reads "LEI-JEN".