Against the backdrop of Manhattan's changing literary and publishing world, aging novelist Leonard Schiller (Frank Langella) is asked by Heather Wolfe (Lauren Ambrose), a graduate student and budding literary critic, to agree to interviews. He's reluctant to spend the time: his health is failing and he wants to finish one more book. Also he's worried about his daughter, Ariel (Lili Taylor), who's approaching 40, underemployed, single and wanting a child. But he agrees, hoping Heather can help resurrect interest in his work. As Heather probes Frank's writing and his past, Ariel reconnects to a former lover. Emotions can be raw and messy, and as relationships change, who gets the better part of the bargain?