"A Wake" tells the story of James Cole, a high-school English teacher who has begun to despair of inspiring in his students the same love of language and literature that first motivated him to teach. When he assigns Eugene O’Neill’s "Long Day’s Journey into Night," one of his students, an aspiring actress named Dana, unexpectedly connects with the play, reawakening in James the enthusiasm he feared he had lost, not only for teaching, but for living life to its fullest potential. It is a reawakening that prompts him at last to seek the truth about his own family's history, and the ways in which he has allowed the ghosts of his past to shape his present and future.

One ghost in particular haunts James’s imagination: a young woman named Hannah Finch, his grandfather’s first—and perhaps only—love, who died in childbirth nearly a century ago. Through his conversations with Hannah, James learns that his grandfather wasn’t always the gloomy man of memory—he was young once and possessed with a joy for living that seems both wonderful and hopelessly alien to James.

Inspired by his discovery, James throws himself into teaching with greater intensity than ever, but his students continue to resist his efforts. James must decide whether the fault lies in them or in his unrealistic expectations of them, and his conclusion leads him to draft his letter of resignation. In the play’s final scene, Dana returns to recite a speech she has prepared from "Long Day’s Journey into Night." James watches Dana’s performance, greatly moved, as the letter lies forgotten on his desk.