This chapter discusses D.H. Lawrence’s introduction to psychoanalytic ideas in March 1912 by Frieda Weekley, who had had an affair five years previously with the maverick psychoanalyst Otto Gross. Gross’s differences from Freud are explored in matters of psychology and politics, focussing on his anti-patriarchal critique of the idea of transference which he saw as replicating the authoritarian power-structures of bourgeois society. Gross was a Stirnerian individualist and sexual liberationist who believed that internal conflict was interpersonal rather than intrapersonal in origin, and whose ‘new ethic – explored here – was grounded in anarchist politics and relational psychology. He was also a cocaine addict whom friends considered a fanatic. The chapter presents the paradoxes involved in dealing with a person whose behaviour, ethics and politics were at odds with the prevailing mores of society, and illustrates the efforts of Frieda, her sister Else, Max and Marianne Weber, Franz Jung and others, and also the diagnostic attempts of Freud and Jung, to reach an understanding of him. It was also a struggle that would engage Lawrence all his life as he grappled with Frieda and the influence of Gross on her ideas of herself and the nature of the good life.