Up-and-coming sports shoe entrepreneur Steve, who is still reeling from the death of his dad, has made a "November rule" in order to keep his distance from the women who seem to be getting too serious about their relationship. Every November 1st, Steve makes up a whopping lie in order to break up with his current girlfriend. However, this year, when he gives the beautiful Leah her walking papers, he realizes his immature and arbitrary rule has just lost him the woman of his dreams. But whether he can win Leah back seems increasingly doubtful, especially after she starts dating pro sports star, James Avedon.