Kevin (LANCE BASS) is a young, Chicago-based adman who's never been lucky at love simply because he's never had the courage to connect with the right woman. Accordingly, when he meets Abbey (EMMANUELLE CHRIQUI) one day on the L train and they immediately hit it off, he blows his chances when he neglects to ask for her name or number.
After being assigned to a new Reebok campaign by his boss, Mr. Higgins (DAVE FOLEY), and then watching his senior partner, Jackie (TAMALA JONES), steal his idea and take credit for it, Kevin decides not to be a pushover any longer and thus sets out to find Abbey.
Since he has no idea who or where she is, he places fliers all across the city looking for her. They draw the attention of a newspaper editor who assigns reporter Brady (DAN MONTGOMERY) to cover the story, thus drawing citywide awareness to the romantic plea. Soon, scores of women are interested in Kevin, a point that his friends Rod (JOEY FATONE), Randy (JAMES BULLIARD) and Eric (GQ) quickly take advantage of by acting like him so that they can get quick and free dates.
Yet, their fraudulent actions soon threaten Kevin's chances of finding Abbey as public sentiment turns on everyone questioning the validity of his quest. From that point on, and armed with advice from Nathan (JERRY STILLER), an older coworker, Kevin does what he must to find Abbey.