An awkward and shy high-schooler, Ted (Ben Stiller) lands a prom date with his dream girl Mary (Cameron Diaz), just to have it cut short by a painfully humiliating zipper accident. Thirteen years later he's still in love?maybe even obsessed?with the one that got away, so he hires sleazy private detective Pat Healy (Matt Dillon) to track her down living in Miami, only to have Pat fall for the irresistible Mary as well. Ted and Pat resort to lying, cheating and stalking in their competition for Mary, and discover that they're not the only men who will use depraved measures to be near her.