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Emily Jackson (Brittany Murphy) lives a fast-paced life. Always on the go, able to talk around the clock, with a sensitive soul she loves playing matchmaker for her friends. It's Emily's gay roommate and frequent companion Peter (Matthew Rhys), who becomes again the subject matchmaking skills when handsome new photographer assistant Paolo (Santiago Cabrera) arrives at the Vogue offices, where Emily works. She makes it her mission to bring the two men together. Unfortunately for her, she is so busy arranging a love connection between Peter and Paolo that she remains completely blind to the one suitor who longs to provide her with the loving companionship that she so cheerfully arranges for others. And so it does make sense that Peter, a screenwriter in the making, starts telling the story from his own point of view.