Working with couples from a classical perspective can be thought of as an oxymoron, unlike working from object relations and relational viewpoints, often seen to be the more natural fits. This article offers a fresh look at those parts of the classical perspective that relate very clearly to working with two partners in a couple. Freud’s theories in Three Essays on the Theory of Sexuality (1905) and On Narcissism (1914a) provide theoretical background for the work. Concepts such as transference (between partners, between the partner[s] and the therapist) and countertransference are shown to be manifested in complex ways with couples. Being mindful of unresolved developmental issues—for example, Oedipal and separation-individuation issues—which may have played a part in partner choice and in the resulting problems, allows the therapist to offer deep interpretations of within- and between-partner conflicts. Interestingly, unresolved Oedipal issues, particularly, may form an important part of the countertransference.