In this romantic comedy of mistaken identity, Oscar Novak (Matthew Perry) and Peter Steinberg (Oliver Platt) are a pair of struggling but talented Chicago architects given the chance of a lifetime: Charles Newman (Dylan McDermott), an extremely wealthy business tycoon, is considering hiring them to design a multi-million dollar cultural center. However, Oscar and Peter aren't the only ones who've been asked to contribute ideas for the project; Decker and Strauss (John C. McGinley and Bob Balaban), two highly successful designers that Oscar and Peter used to work for, have also been approached by Newman, who thinks that a competition between the two teams would be good fun and good press. Oscar is determined to show his dedication to the job, so when Newman asks him to start keeping tabs on his girlfriend Amy (Neve Campbell), he's happy to oblige. Oscar proves a sad excuse for a private eye, and finds himself falling in love with the woman that he's supposed to trail. To complicate matters, Charles gave Oscar the assignment because he was sure that Oscar is gay, and he hasn't been shy about telling people; soon Amy is convinced, along with most of Chicago. And while Oscar doesn't want to upset Newman, he also doesn't want to start living a lie, especially one that would keep him away from the woman he loves. So when Oscar is named Chicago's Gay Professional of the Year, what's a (straight) guy to do?