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Photographer Kat Matthews believes life is an adventure, to be taken at leisure. When vacationing with her mother in Vale, Colorado, she meets an eccentric, rich couple who have a bizarre proposition. They want to hire her to date their son. But not just date him—they want her to train him in how to date, so he'll continue doing so afterward. As payment, they dangle a once in a lifetime opportunity in front of Kat—the chance to have her photographs seen by the owner of the most prestigious art gallery in New York.