A young woman and her gay best friend test the limits of their friendship as they vie for the attention of the same man. She’s positive he’s straight, her friend’s sure he’s gay. They’re all unaware he’s a twin.
AMY and ETHAN guy watch at their favorite coffee place. Ethan, who’s gay, has been trying to teach Amy how to tell the difference between gay and straight men since college with little success. JAMES McKENNA walks down the street and both think he’s hot. However, they disagree on his sexuality. Amy finds out the next day that James has been hired by her firm. Ethan and Amy continue their disagreement on James’ orientation. Finally, they decide to wager on James’ sexuality. Each will have two weeks to prove on which side of the fence he’s on. Later, Ethan, a photographer, is taking photos for a club in West Hollywood. There he meets JUSTIN SHIELDS, a dead ringer for James. Due to the fact, unknown to Ethan, that Justin’s company uses Ethan as a photographer Justin introduces himself as JJ Smith. Ethan thinks that this is suspicious and takes pictures of him on the dance floor that he shows to Amy the next morning. In Ethan’s view, he’s proven that James is gay. Amy’s not convinced. James asks Amy out, takes her to the ballet, introduces her to his sister SANDRA, and almost runs into Justin also attending the ballet.
James asks Amy to go with him to a dinner meeting. Ethan runs into JJ (Justin) again while taking more pictures and JJ asks Ethan out to a Laker’s game. After the game, at Ethan’s front door, JJ impulsively kisses Ethan. Barely missing running into James at the elevator, JJ leaves, while James calls for Amy at her condo across the hall from Ethan’s. After the dinner, James walks Amy back to her condo. He kisses her, but when it looks as though things may go farther, James gets cold feet and leaves. Ethan is feeling guilty and is avoiding Amy, until finally Amy confronts him and each admits that James, or who they thought was James, kissed them. They decide that the time has come to ask James what his sexuality is. Both have been invited to dinner, Amy on Saturday and Ethan on Sunday. Things don’t go according to plan. Amy succumbs to James’ charm and Ethan does the same with JJ. This causes a rift between Amy and Ethan and they stop speaking. By a strange twist of fate, both couples check into the same spa on the same weekend and James and JJ get mixed up, with Amy trying to seduce JJ and Ethan going after James. Amy and Ethan run into each other and argue. Unseen, James and JJ hear the details about the bet and leave, saddened. James runs into Ethan and Amy before he leaves and gives them a piece of his mind.
From there, things go from bad to worse. Amy and Ethan are still not talking, James takes a position with another firm and Amy’s boss blames her for his departure, and JJ has cancelled Ethan’s contracts with his company without telling him the truth of his identity. Amy appears at Ethan’s door and the two of them are reconciled and decide to go out to their favorite bar and get blitzed. At the bar ahead of them are both James and Justin. Justin has been there for awhile when James arrives. A misunderstanding causes Justin to throw a punch at James, knocking James to the floor. It’s only then that the two of them see the resemblance between them. When Amy and Ethan arrive, it starts a chain of events that becomes even more shocking when James’ sister Sandra has revelations of her own that will change all their lives forever.