Grady Tripp (Douglas) is a professor/writer living in Pittsburgh who is struggling with writer's block. Whilst doing this, he also manages to get the chancellor (McDormand) pregnant. In the meantime, he and a college student, James Leer (Maguire) are trying to find a rare jacket once owned by Marilyn Monroe, and a college girl, Hannah Green (Holmes) boarding with Grady has a bit of a crush on him. Based on the book of the same name by Michael Chabon.