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Devin thought that finishing college was a destination, not a point of departure. So for him, life has been made difficult by the fact that everything didn't fall into his lap when he got his degree. An extended period of professional inactivity has put a strain on his marriage with his wife, Janet, who is fed up with him and is preparing to file for divorce if he doesn't shape up. To clear his head, Devin jogs through a nearby park. It is here that he meets Benjamin, an eccentric old man that Devin sees playing chess everyday he jogs. Out of curiosity, Devin sits to play a game with Benjamin. A friendship between the two blossoms as Benjamin uses the game of chess to teach Devin important life lessons to motivate and inspire him to put his life back together. But even with Devin receiving this new sense of determination from this unlikely mentor, is it too little, too late for Devin? As we explore Devin and Janet's relationship, in the past and present, can Devin ensure that it will have a future? All roads lead to the climax as Benjamin gives Devin a reality "checkmate" and pushes Devin to the edge of his capabilities, and nerves, to save his marriage, and himself.