Leonard Schiller is a writer in his seventies. All of his books are out of print; he's left no mark in literary history; a lifetime of dedicated labor has brought him few rewards. Heather Wolfe is a graduate student in her twenties. She read Schiller's novels when she was growing up, and they changed her life. She decides to write her master's thesis about Schiller's work, and she sets out to meet him.

Starting Out in the Evening is a novel about the unexpected consequences of that meeting - and the unexpected consequences of art. Heather blows into Schiller's life like a whirlwind and overturns everything in it. After years of obscurity, he finds himself dreaming of literary immortality; after a lifetime of restraint, he finds himself infatuated with a woman "so young she seemed like an emissary from the future.".

For Heather, meeting Schiller has even more complicated results. Finding it hard to believe that this cautious, habit-bound man wrote the books that taught her so much about the beauty of taking risks, she begins to suspect that her idol has failed to understand the deepest lessons of his own art.

In the course of the novel, we also come to know Schiller's daughter, Ariel, a spirited and tender-hearted former dancer, and her lover, Casey, a restlessly self-questioning black intellectual. Though deeply committed to each other, they are pursuing irreconcilable dreams, and together they are facing the fear that their conflicts will prove greater than their love. When Schiller's fortunes change dramatically, Ariel and Casey are put to a test that neither of them could have prepared for.