Ben and Jeff are about to take their successful Internet startup company public and hit the jackpot for which they have been working so diligently. Ben is dating a beautiful yoga instructor named Caitlin, while Jeff is seeing Sara, an ambitious model. However, the men decide that they are suspicious enough of their respective girlfriends' intentions to set up a little test of their fidelity, and each sets out to seduce the other's lover.

Lacking experience to write her research paper on sexual behavior, a 22-year old college student responds to personal ads to broaden her erotic horizons.

Matthew is young and ambitious, a businessman already achieving success. Although he is experienced in the matters of sex, he was never prepared for Valerie. She is a revolution in all matters of emotion and sex that Matthew believe he knew. He becomes obsessed with her and that will lead to his own downfall.