Struggling graphic novelist John Hollar (John Krasinski), who lives in New York City, returns to his hometown when his mother, Sally (Margo Martindale), is diagnosed with a brain tumor. He gets there just before she goes in for surgery.
John and his girlfriend Rebecca (Anna Kendrick), who is eight months pregnant with their first child, get caught up in his dysfunctional family's problems. He must also face his high school buddies, his high school rival, and an overeager ex-girlfriend, in the crazy world that he thought he had left behind.