In this modern update on Cinderella, a prostitute, and a wealthy businessman fall hard for one another, forming an unlikely pair. While on a business trip in L.A., Edward (Richard Gere), who makes a living buying and breaking up companies, picks up a hooker, Vivian (Julia Roberts), on a lark. After Edward hires Vivian to stay with him for the weekend, the two get closer, only to discover there are significant hurdles to overcome as they try to bridge the gap between their very different worlds.
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.