In response to political, technological, and sociocultural changes, the family unit built around a mother and father who are married to each other has been joined in recent decades by a range of other models, including, among others, male same-sex families. These families challenge the narratives of classic psychoanalysis, which relate explicitly to the traditional model. This article examines the potential for conflict and the possibility of coexistence between male same-sex families and basic psychoanalytic concepts such as Oedipus complex, identification with the same-sex parent, the good-enough mother, and primary maternal preoccupation. It adopts a postmodern perspective and makes use of clinical vignettes. This article also considers the clinical implications that may result from the encounter between male same-sex parents and therapists relying on the orthodox interpretation of classic concepts. These include the influence of a therapist’s conscious or subconscious beliefs regarding the desired family model, which are derived from a set of internalized attitudes and fantasies, social and professional socialization, theoretical interpretations of psychoanalytic concepts, and so on. This article calls for further exploration of the applicability of classic psychoanalytic concepts to other types of new families, such as female same-sex parents and single-parent families.