This chapter discusses Sigmund Freud’s “Observations on Transference-Love” from the viewpoint of amae. Freud begins his paper “Observations on Transference-Love” with a reminder that the only really serious difficulties in conducting psychoanalysis lie in the management of the transference. He cites as a typical example the case of a woman who falls in love with her analyst. Having established the genuineness of the transference love, Freud comes back to the fact that nonetheless it is provoked by the analytic situation. The chapter focuses on a woman patient, who almost came to articulate her wish for amae. Amae, a Japanese word, signifying “indulgent dependency,” primarily describes what an infant feels when it seeks its mother. Interestingly, it can also be applied to an adult when that person is supposed to entertain a similar feeling of being emotionally close to another.