At Middleton

Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and tries to convince him to stop pursuing Amanda. Matters are further complicated when Keith's invitation draws the ire of Amanda's rich yet snobby ex-boyfriend, Hardy Jenns, who makes plans to get even.

With the occasion all but overshadowed by her sister's upcoming wedding, angst-ridden Samantha faces her 16th birthday with typical adolescent dread. Samantha pines for studly older boy Jake, but worries that her chastity will be a turnoff for the popular senior. Meanwhile, she must constantly rebuff the affections of nerdy Ted, who is unfortunately the only boy in school who seems to take an interest in her.

A wealthy executive, Drew Latham (Ben Affleck) has no close relationships and becomes nostalgic for his childhood home as Christmas approaches. When he visits the house and finds another family living there, he offers the residents, Tom Valco (James Gandolfini) and his wife, Christine (Catherine O'Hara), a large sum of money to pretend they are his parents. Soon Drew tests the couple's patience, and, when their daughter, Alicia (Christina Applegate), arrives, things get increasingly tense.

Self-made millionaire Thornton Melon decides to get a better education and enrolls at his son Jason's college. While Jason tries to fit in with his fellow students, Thornton struggles to gain his son's respect, giving way to hilarious antics.

Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.