Jaime Sharma is a self-described guy's girl who lives in an upscale Manhattan apartment with her lawyer boyfriend and who works as an assistant to a famous architect. All her life, she's only been friends with men. After Jaime and her boyfriend break up, all of her guy friends profess their secret, undying love for her. Jaime turns to Ted, her best friend from college who just moved to the city, for his typical, gentle advice. Instead, she's challenged by advice from Ted's brash girlfriend Sandy, who, for the first time in Jaime's life, tests Jaime's views about male friendship and about herself.