Aspiring athletic shoe businessman Steve, still coping with the loss of his father, has devised a “November rule” to maintain emotional distance from women who appear to be getting too serious about their relationship. Each year on November 1st, Steve concocts an elaborate lie to end things with his current girlfriend. This time, however, when he breaks up with the stunning Leah, he comes to the realization that his childish and capricious rule has cost him the love of his life. Winning Leah back seems increasingly unlikely, especially now that she has begun seeing professional athlete James Avedon.