How do two people find love in New York City? Barry and Justine meet on an airplane over LaGuardia airport just before the Christmas holidays. Barry is a food product manager who hasn't had a date in a year. He lives in his parents' old Upper West Side apartment and has taken in a spoiled, rich roommate who has three simultaneous girlfriends but never has the rent. Barry's colleagues at work are all married, so are his friends - and most of them are having children. He really wants to find 'the one'. Justine is a pretty, smart and ambitious lawyer on the partner track at a hotshot New York mergers and acquisitions firm. She is sick of the dating scene and has had a string of bad luck. Her friends and colleagues keep trying to fix her up, but her patience is running out. She'd rather be home at her apartment on the Upper East Side with her dog, drinking salad dressing for dinner and watching The Sound of Music on the VCR. These two meet under the most dangerous, absurd and ultimately romantic circumstances. But will they realize that they're made for each other?