Oscar Novak (MATTHEW PERRY) and his business partner, Peter Steinberg (OLIVER PLATT) are two up and coming Chicago architects who've approached local tycoon Charles Newman (DYLAN McDERMOTT) to financially back their design for revitalizing an old landmark into a multimillion dollar cultural center.
Impressed by their plans, Newman not only agrees to back them, but also asks Oscar if he can keep his eye on his mistress, Amy Post (NEVE CAMPBELL), a local glass blowing artist. Thinking she might be seeing any number of old boyfriends including football star Kevin Cartwright (CYLK COZART), Newman isn't worried about Oscar tagging along with her since everyone, including his assistant, Lenore (DEBORAH RUSH), believes that he's gay.
Sensing that their career enhancing project is on the line, Oscar reluctantly agrees to spy on Amy. Upon first seeing her, however, he's immediately smitten and she hits it off with him as well. That's probably because she thinks he's gay as well, and soon everyone in town believes the same, a fact that's quite funny to Peter since he's the gay one.
As Oscar becomes even more attracted to Amy, he must decide how to proceed with her, particularly as his gay reputation grows, and must deal with any number of complications, such as Amy finally meeting Newman's wife, Olivia (KELLY ROWAN), that threaten to upset the tycoon and thus ruin their deal.