College sophomore William Pastor isn't too thrilled to hear his boyfriend of almost a year, Ethan, will have to work on Valentine's Day, dashing his plans of a day trip to the Hollywood sign and dooming him to spend Valentine's Day alone. Before Will can become too furious, however, he opens a letter from a local TV station and is shocked to learn he has been chosen as the winner of the Valentino's Valentine contest, granting him a date with TV and movie star Vincent Valentino on the Day of Love. Despite Ethan's discomfort with the idea of his boyfriend going out with another man on Valentine's Day, Will is ecstatic. Once Valentino shows up, however, things start to feel strange. The date is everything he imagined, and yet, something is missing. Is Will's happily-ever-after with the gorgeous, successful movie star flashing megawatt smiles his way and taking him to lunch at an expensive Italian restaurant? Or is it all the way across town, waiting tables at a local restaurant and silently hoping Will won't be swept away by the false promise of Hollywood charm?