While vacationing with her mother in Vale, Colorado, photographer Kat Matthews meets an eccentric, rich couple who have a bizarre proposition. They want to hire her to date their son. And not just date him, but train him 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 are gallery in New York.