During a snowy winter in the small fictional town of Knight's Ridge, Massachusetts, a group of lifelong buddies hang out, drink and struggle to connect with the women who affect their decisions, dreams and desires. Tommy "Birdman" Rowland and Kev, his sidekick, plow snow for a living. A former campus stud, Tommy continues to harbor feelings for his ex-girlfriend Darian, complicating his relationship with current lover Sharon. Paul Kirkwood lives with Birdman and also plows snow. Inexorably drawn to supermodels and the "ideal" woman, he refuses to commit to Jan, his girlfriend of seven years. Traveling from New York where he works the piano bar circuit, Willie Conway is at a crossroads in his life. Although he lives with sharp attorney Tracy Stover, Willie cannot commit to the relationship. In Knight's Ridge, he meets Marty, a 13 year-old "heartbreaker in training" and Andera, Stinky's cousin from Chicago, who compel Willie to reassess the value of his life and his relationship with Tracy.