Writer Nate Piven's star is rising. After several lean and striving years, he has his pick of both magazine assignments and women: Juliet, the hotshot business reporter; Elisa, his gorgeous ex-girlfriend, now friend; and Hannah, "almost universally regarded as nice and smart, or smart and nice," who holds her own in conversation with his friends. When one relationship grows more serious, Nate is forced to consider what it is he really wants.

In Nate's 21st-century literary world, wit and conversation are not at all dead. Is romance? Novelist Adelle Waldman plunges into the psyche of a flawed, sometimes infuriating modern man—one who thinks of himself as beyond superficial judgment, yet constantly struggles with his own status anxiety, who is drawn to women, yet has a habit of letting them down in ways that may just make him an emblem of our times.