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Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.

Eugene, a young teenage Jewish boy, recalls his memoirs of his time as an adolescent youth. He lives with his parents, his aunt, two cousins, and his brother, Stanley, whom he looks up to and admires. He goes through the hardships of puberty, sexual fantasy, and living the life of a poor boy in a crowded house.

Photographer Robert Kincaid wanders into the life of housewife Francesca Johnson for four days in the 1960s.

A young woman is forced to reflect on her first relationship when she inadvertently moves into her ex boyfriend's apartment building.

During the Second World War, Eugene enlists in the US Army during the last year of the War and is sent to basic training in Biloxi Mississippi. There he must live with a variety of fellow soldiers while enduring the whims of a mentally unstable drill sergeant.

The story follows the misadventures of a New York City beautician who is mistakenly hired as the school teacher for the children of the president of a small Eastern European country.