Travis Prescott has it all, a great life with a great job that allows him the freedom to enjoy his favourite hobby; seducing women. When he comes to New York City for his younger brother, Justin’s wedding and meets Marissa, the bride; he decides that there are some women not worthy of his efforts. As the wedding looms, Travis senses Justin’s growing cold feet. Playing on that, Travis makes him a cruel wager; that Justin cannot leave Marissa at the altar and win her back within the year. Thus begins the game as Travis tries to gain Marissa’s trust and keep her from forgiving Justin. Yet the game may not be what it seems when Travis decides that it is he, not Marissa who is unworthy. There are some hearts that shouldn’t be broken and some passions that shouldn’t be explored. What happens when the player forgets his own rules?