This paper discusses two kinds of complexities inherent in psychoanalysis' concept of transference. The first kind: transference emotions usually appear in the shape of polarities – that is, an emotion is accompanied by its opposite that may be manifest or latent. This is true both of emotions that are split off and ambivalent. In addition, two or more such polarities often co-exist, running like parallel tracks, e.g., an aggression polarity together with a dependence polarity. A clinical vignette illustrates this train of thought. The second kind: Starting from Winnicott's concept of transitional phenomena, the epistemological status of the transference concept is discussed. Transference phenomena take place in an intermediate area between reality and phantasy, and between past and present. The ensuing paradoxes that will characterize the concept-formation have to be accepted and respected. Some technical consequences of these complexities are discussed.