Jack Holmes is suffering from unrequited love. It doesn't look as if there will ever be anyone else he falls for: the other men he takes to bed never stay for long. Jack's friend Will Wright comes from old stock, has aspirations to be a writer and, like Jack, works on the Northern Review. Jack will introduce Will to the beautiful, brittle young woman he will marry, but is discreet about his own adventures in love — for this is sixties New York, literary and intense, before gay liberation; a concoction of old society, bohemians rich and poor, sleek European immigrants and transplanted Midwesterners. Against this charged backdrop, the different lives of Jack and Will intertwine, and as their loves come and go, they will always be, at the very least, friends.

The famed writer Stephen Crane is travelling to a German clinic in search of a cure for the tuberculosis that threatens his life. Knowing it may be his last chance, he dictates the story of The Painted Boy, inspired by a real-life encounter. But as the story delves into the seedy underworld of turn-of-the-century Manhattan, Crane's health deteriorates and the outcome of the story becomes as critical as the author's life itself.