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High school sophomore Samantha "Sam" Baker has a big crush on Jake Ryan, who she believes does not know that she exists. He is, in fact, aware of her and, though he is in a relationship with prom-queen Caroline, his interest in Samantha begins after finding a note about him written by her.
Ginny, Samantha's older sister, is getting married and the entire family's attention is focused onto her rather than onto Samantha's upcoming sixteenth birthday. On the eve of Ginny's wedding, Samantha's entire family forgets her birthday. In the midst of pre-wedding chaos, a weird foreign exchange student Long Duk Dong visits the Bakers' home as the guest of his hosts Grandma and Grandpa Baker. Her family forces her to go to a dance with him. She abandons him at the event, but he meets another girl there and they're inseparable for the rest of the night. Meanwhile, Samantha becomes upset when she sees Jake dancing with his girlfriend, Caroline Mulford, and then her unwanted admirer, a geeky freshman named Ted, very awkwardly tries to dance with her.
To win a set of floppy disks, Ted bets with his friends that he will sleep with Samantha ("By night's end, I predict me and her will interface.") and bring back her underwear as proof. Following Samantha into the shop room, Ted makes a couple of unsuccessful attempts to accomplish his goal. Their ensuing conversation includes Ted's admission that he has "never bagged a babe" and Samantha exposing her crush on Jake. Ted's confrontation with Jake in the gym just prior revealed Jake's apparent interest in Samantha, and Ted recounts what was said. After talking and getting to know each other, Ted confesses the wager and suggests an alternative. Samantha gives Ted her underwear to help him out.
Later (after a peep show of Samantha's underpants for $1 admission), the geek and his equally unwelcome friends Cliff and Bryce attend a senior after-party at Jake's ("party hardy dude-person") which ends up into a complete disaster that almost destroys the house. At night's end, Jake finds Ted trapped under a table, and they too chat. Ted explains to Jake the situation with Samantha and gives him her underwear. In return, Jake lends Ted a car - his father's Rolls Royce convertible - as well as his fully inebriated girlfriend Caroline.
Meanwhile, Samantha's parents apologize about forgetting her birthday, and Samantha confides to her father about her crush who "doesn't know she exists." He tells her to go and talk to Jake, and to not let him overpower her.
After a wild night with the drunken Caroline, during which he attempts to record his unbelievable fortune in a botched photo, Ted and Caroline wake up in a church parking lot in the back seat of a Rolls Royce. Caroline reveals to an unsure Ted that they had sex during the night, and that she thought it was "sweet", delighting Ted. Jake finds them in the parking lot and breaks up with Caroline on friendly terms. He then goes to find Samantha, whom he tried unsuccessfully talk to the whole night.
Ginny's wedding proceeds despite her menstrual cramps and a mild overdose of muscle relaxants, which result in a comedic ceremony. Upon exiting the church, the wedding party slowly dissipates, and Samantha is left standing alone. Jake is seen leaning against his Porsche across the street and gestures to Samantha, which, at first, bewilders her.
In the subsequent and final scene, to the archetypal 1980s pop-ballad "If You Were Here" by the Thompson Twins, the profiles of Jake and Samantha can be seen lit by the candles of a birthday cake between them. Jake asks her to make a wish which she says has already come true. They kiss.
