Joel Goodson is a normal high school student who lives with his wealthy parents in the North Shore area of suburban Chicago. His father wants him to attend Princeton University, his alma mater, so Joel participates in Future Enterprisers, an extracurricular activity in which students work in teams to create small businesses.
In the Victorian period, two young cousins, Richard and Emmeline Lestrange, and a galley cook, Paddy Button (Leo McKern), survive a shipwreck in the South Pacific and reach a lush tropical island. Paddy cares for the small children and forbids them by "law" from going to the other side of the island, as he found evidence of remains of bloody human sacrifices. He also warns them against eating a scarlet berry which is apparently deadly.
The story centers on Eugene Morris Jerome, a 20-year-old Jewish Brooklynite who is drafted into the United States Army during the last year of World War II and is sent to Biloxi, Mississippi for basic training. While there he learns to cope with fellow soldiers from all walks of life, falls in love, and loses his virginity in less than ideal circumstances, all while having to cope with an eccentric drill instructor.
In 1973, William Miller is a 15-year-old boy aspiring to be a rock journalist. His mother, Elaine, wants him to become a lawyer. Shunned by his classmates, he writes for underground papers in San Diego, sharing the love of rock music instilled in him through a gift of albums left behind on the day his sister Anita left home.
The plot begins with the portrayal of the Massacre of the Innocents in the Nativity. The remainder of the movie portrays the annunciation (conception) and birth of Jesus Christ to explain why King Herod the Great (Ciarán Hinds) ordered the murder.
A group of teenage girls from the Atlanta area go to summer camp, and two of them make a bet as to which one will lose her virginity first. The two girls then choose "targets", or guys they want to be the ones they lose their virginity with. Unbeknownst to the adults, all the girls in camp bet money on the contest and divide into two "teams," each rooting for and egging on either Ferris (Tatum O'Neal) or Angel (Kristy McNichol). At the same time, the girls engage in typical teenage behavior, such as food fights and other activities.
The film is narrated by Charlotte Flax, a 15-year-old girl living in Oklahoma with her glamorous but eccentric mother, Rachel (whom she calls "Mrs. Flax"), and 9-year-old sister, Kate, who calls her by her given name. The narration begins in early fall 1963, just as Rachel's latest fling with her married employer ends and she decides to relocate once again. This time, they move to a new home near a convent in the small town of Eastport, Massachusetts. Charlotte has an obsession with Catholicism and idolizes the nuns living in the convent. She is always reminded by Rachel that they are Jewish. Kate, on the other hand, loves oceans and swimming. She apparently learned to do so when she was a baby, allowing her to win many competitions.
The film opens with a series of still photographs appearing over melancholic music, representing the abstract memories of the unseen Herman Raucher, now a middle-aged man. We then hear Raucher recalling the summer he spent on the island in 1942. The film flashes back to a day that then 15-year-old "Hermie" and his friends – jock Oscy and introverted nerd Benjie – spent playing on the beach. They spot a young soldier carrying his new bride into a house on the beach and are struck by her beauty, especially Hermie, who is unable to get her out of his mind.
Erik Stifler (John White) has a difficult time living up to his family name. He is Steve and Matt Stifler's cousin. He is perhaps the only Stifler about to graduate from high school as a virgin. The film opens with Erik feigning illness so that he can stay home and masturbate. Unfortunately, just as he is about to ejaculate, his parents and grandmother unexpectedly walk into the door and are hit with Erik's semen, after which his grandmother dies of a heart attack. Erik's dad later surmises that, as a Stifler, his son should be out having sex instead of masturbating. Erik's girlfriend of two years, Tracy (Jessy Schram), loves him, but is not ready for intercourse. Tracy decides to have sex, their first attempt goes horribly wrong, and she backs out of trying again.
Brad Hamilton is a popular senior who is looking forward to his last year of school and almost has his 1960 Buick LeSabre paid off. He has a part-time job at a burger joint, "All American Burger" where his girlfriend, Lisa, also works. This esteemed establishment has a strict policy of etiquette: "No Shirt, No Shoes, No Dice". He is pondering how to end his relationship with Lisa so he can play the field during his senior year. However, Brad is fired for losing his temper at an obnoxious customer; when he tries to tell Lisa how much he needs her, she says she is dumping him to see other guys. Brad quits his next job at Captain Hook Fish & Chips because of the humiliation of having to wear a pirate costume when delivering food. He gets a job at a convenience store, Mi-T-Mart, where he successfully thwarts an attempted robbery and is promoted to store manager.
Philip "Philly" Fillmore (Eric Brown) is the 15-year-old son of a rich businessman in Albuquerque who has left town on an extended summer trip, leaving the young man in the passing care of Nicole Mallow (Sylvia Kristel), a sexy French housekeeper, and Lester Lewis (Howard Hesseman), the family's chauffeur.
High school sophomore Samantha "Sam" Baker (Molly Ringwald) struggles to get through the day on her 16th birthday, which her entire family has forgotten about because her older sister, Ginny, is getting married the next day. She is also plagued by infatuation with a popular and attractive senior, Jake Ryan (Michael Schoeffling). At school she fares no better when she finds out that a completed "sex quiz," which she tried to surreptitiously slip to her friend, never reached her friend and, unbeknownst to either of them, was picked up by Jake. Sam panics because the quiz contains sensitive information, such as she is a virgin and is saving herself for Jake.
The movie opens with scenes of an aerobics class juxtaposed with a classroom of students taking an examination. The movie's two protagonists are featured in these scenes, with Terry Green (Caren Kaye) participating in the aerobics and Bobby Chrystal (Matt Lattanzi) taking, not very well it turns out, his last high school final, in French.
When Jonathan Ogner (Andrew McCarthy) first shows up to prep school, he is laughed at for wearing his school uniform. He then goes up to his dorm and meets his new roommate (Rob Lowe), who introduces himself as Squire Franklin Burroughs IV but tells Jonathan to call him "Skip." Skip then takes off his trench coat and is shown to be wearing a red bra and girls' underwear. He explains to the shocked Jonathan that it isn't what it looks like and that it's a tradition for the seniors to parade around campus wearing only girls' underwear. When Jonathan doesn't have any, Skip gives him a set that he had in his dresser. Skip and Jonathan travel out of the dorm together until they get to the final door where Skip stays behind and locks the door. The other students begin to laugh and mock Jonathan for wearing girls' underwear. Mortified, Jonathan attempts to flee the scene. After discovering that Skip has locked all the doors, Jonathan climbs a trellis that leads into his dorm where he finds Skip lying on the floor laughing hysterically.
The film opens with 16-year-old Telly (Leo Fitzpatrick) and a 12-year-old girl who are making out on a bed. With no adults around, Telly convinces the girl, who is a virgin, to have sex with him. Afterwards, he meets his friend, Casper (Justin Pierce), and tells him about his sexual experience in graphic terms. They go inside a local store, where Casper shoplifts a bottle of malt liquor as Telly distracts the cashier. Looking for drugs, food and a place to hang out, they head to their friend Paul's (Sajan Bhagat) apartment, though they express dislike of him on the way there. They arrive at Paul's house, talk about sex and smoke marijuana while watching a skate video (Video Days). Casper inhales nitrous oxide out of balloons, which Telly considers dangerous. The scene intercuts with a group of girls, among them Ruby (Rosario Dawson) and Jennie (Chloë Sevigny), talking about sex—each gender contradicting what the other gender says, especially about oral sex.