This paper explores the centrality of the re-working of Oedipal issues during adolescence to a person's eventual capacity to enter into and to sustain an intimate couple relationship. It does so by drawing on representations of this process in classic literary texts (namely in George Eliot's Middlemarch and, glancingly, in Shakespeare's Comedies) to elucidate non-pathological struggles towards maturity. It also draws on the consequences of a failure of an Oedipal ‘working-through’ in the dream material of a young man whose attempts at intimacy were severely hampered by early developmental ‘road-blocks’— ones that were rooted in an early Oedipal impasse.