I think it's a mistake to assume that every song is autobiographical. I always find this one rather funny - he's writing in the persona of the kind of man who constantly screws up but thinks he can get away with it with his boyish charm & aw-shucks honesty. When he's talking about the prostitute I can just see his wife/girlfriend kicking him out of the door. It cracks me up! Waits can be horribly sentimental sometimes, but I think he gets away with it here because of the humour.
I think it's a mistake to assume that every song is autobiographical. I always find this one rather funny - he's writing in the persona of the kind of man who constantly screws up but thinks he can get away with it with his boyish charm & aw-shucks honesty. When he's talking about the prostitute I can just see his wife/girlfriend kicking him out of the door. It cracks me up! Waits can be horribly sentimental sometimes, but I think he gets away with it here because of the humour.