This chapter considers Mahler’s active romantic life, asking how this well-known side of his private personality can be reconciled with his compositions’ lack of erotic energy and his general predilection for what we might call an aesthetics of abstinence. From the beginning, Mahler had no less trouble building a healthy connection with a romantic partner than he did putting to rest the existential doubts that drove him to compose. The categorized nature of the symphonies, that is, the repetitions of attitude and approach – religiose grandeur in the Second and the Eighth, manic “joy” in the Fifth and the Seventh, otherworldly resignation in Das Lied von der Erde and the Ninth – mirror a tendency in his choices of female companions, who likewise embody types: the tormentor, the masochistic pupil, the replacement mother. The chapter focuses on three early affairs, with Josephina Poisl, Johanna Richter, and Marion von Weber, before turning to Natalie Bauer-Lechner and Alma Mahler.