Drawing on Freudian theories about marriage, libido, repression and psychosexual development, this essay highlights the use of sublimation, illusion, and regression in an examination of Kate Chopin’s The Awakening (1899), in order to explore Edna’s escape from misery and the conflicting drives of Eros and Thanatos. The analysis is based on the writings of Sigmund Freud, as well as previous psychoanalyses of The Awakening. Drawing on Freudian theories about marriage, repression and premarital abstinence, this essay illustrates how the disruption in Edna’s psychosexual development, caused by the death of her mother, led her to awaken her repressed libido at a point where she could no longer direct her desire towards her husband. By shifting from the reality principle to the pleasure principle, Edna experienced a new susceptibility to suffering that she tried to escape through illusion and sublimation. When her defenses were insufficient, infidelity became the only option of escape against the threat of neurosis. An analysis of the symbolic representation of the ocean and Thanatos’ drive towards regression and the compulsion to repeat illustrates how every step Edna took towards liberation brought Thanatos closer. In doing so this essay illustrates the complexity of Eros’ and Thanatos’ relationship, and how the same forces that gave the promise of ecstatic fulfillment in life brought Edna closer to oceanic longing, and death.