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Nikki (Ashton Kutcher) is living the dream, using his looks and charm to get ahead on the unforgiving streets of Los Angeles. Manipulative, detached and morally dubious he drifts from one rich, hot, middle-aged female professional to the next. He's the ultimate gigolo/toy boy. But the player is about to be played when he meets his female counter part in Heather, a beautiful waitress in search of a sugar daddy. Nikki is about to learn a valuable lesson that will shake him up and strip away the superficial gleam of his Hollywood Hills lifestyle.