Louis Ives (Paul Dano) was perhaps not meant to be born into the modern world. He's a quiet man whose quiet existence only sparks to life when he's teaching literature set in the 1920s to his students. However, after the headmaster's discovery of him in a compromising position results in his sacking, Louis decides to shake life up, move to Manhattan and become a writer whilst living off his savings. He'll need a room to rent, though. Enter Henry Harrison (Kevin Kline), an even more 'not of this world' personality than Louis.
Henry was once, at least as he explains, a great writer, but his days are currently spent being an extra man for elderly women who require a man to fill the place of their deceased husbands. Don't dare call him a gigolo, though. He doesn't get paid cash for his services, rather he spends time with these widows so he can reap the benefits of their luxurious lifestyles. Fascinated by the bizarre but alluring nature of Henry's world, Louis allows the cantankerous old man to take him under his wing, to teach him the ways of the extra man.