It’s been a year since Casey’s wife died, leaving him the youngest widower in Naples, Florida, and in the throes of a seemingly bottomless depression. Now Casey lives only at night, stuck in his once cozy home, drinking himself blind and listening to the sounds of Ellington, Coltrane, and Davis. Casey’s friends and family have just about given up on him, and he’s certainly given up on himself. That is, until Billie Holiday—or someone who looks just like her—finds her way into his life.

Maybe he’s been listening to too much jazz, and he’s definitely been hitting the bottle, but there’s no mistaking that beautiful, had-some-tough-times voice. She calls herself Eleanora, and what everyone else sees as an imaginary friend, Casey sees as the only thing that can bring him solace. And by the grace of this strange and wonderful woman, he receives something he’s yearned for every waking moment: a chance to spend one last night with his wife, and to overcome the crushing guilt he’s felt since the day she left him.