Kat Stratford (Julia Stiles) is beautiful, smart and quite abrasive to most of her fellow teens, meaning that she doesn’t attract many boys. Unfortunately for her younger sister, Bianca (Larisa Oleynik), house rules say that she can’t date until Kat has a boyfriend, so strings are pulled to set the dour damsel up for a romance. Soon Kat crosses paths with handsome new arrival Patrick Verona (Heath Ledger). Will Kat let her guard down enough to fall for the effortlessly charming Patrick?
Teen misfits Gary (Anthony Michael Hall) and Wyatt (Ilan Mitchell-Smith) design their ideal woman on a computer, and a freak electrical accident brings her to life in the form of the lovely, superhuman Lisa (Kelly LeBrock). She outfits Gary and Wyatt in cool clothes, surprises them with a Porsche and helps them stand up to jerks Ian (Robert Downey Jr.) and Max (Robert Rusler). But, all the while, the boys must hide Lisa’s existence from Chet (Bill Paxton), Wyatt’s nightmare of a big brother.
After a wish turns 12-year-old Josh Baskin (David Moscow) into a 30-year-old man (Tom Hanks), he heads to New York City and gets a low-level job at MacMillen Toy Company. A chance encounter with the owner (Robert Loggia) of the company leads to a promotion testing new toys. Soon a fellow employee, Susan Lawrence (Elizabeth Perkins), takes a romantic interest in Josh. However, the pressure of living as an adult begins to overwhelm him, and he longs to return to his simple, former life as a boy.