A photographer named Rebecca (Jenny McCarthy) finds her boyfriend Richard (Victor Webster) in bed with another woman. Soon after, her professional camera equipment is destroyed in an accident. With nothing else to do, she sets her sights on getting revenge on Richard.
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Her friends - Michelle (Carmen Electra), Carrie (Kam Heskin) and John (Eddie Kaye Thomas) all try to give her guidance as she goes on a series of dates to make Richard jealous. But John secretly harbors a crush on her.
None of the dates go right. One is with a perverted magician, and another, a famous director, ends up vomiting on her blouse.
As the pressure mounts to get her life back on track, Rebecca has to choose between retribution on John or actually making herself happy for once. But how does she choose?