Freud’s paper on the three caskets is revisited. His view that the lead casket represented death is supported by extracts from The Merchant of Venice, in particular the song, “Tell Me Where is Fancy Bred”. It is argued that the acceptance of death is a necessary step in the transformation of romantic love to mature love. With experience of reality a disillusion of romantic idealisation becomes possible, but this means that losses have to be accepted and mourned. It is argued that this is made more bearable if an ironic stance enables an acceptance of the pleasures of romance without believing them to be literally true.