The prevailing model of contract law presumes that fully informed decision-makers exercise free and voluntary choices to further their conscious preferences and goals. The model makes sense in the context of commercial relationships. But family contracts—prenuptial agreements, separation agreements, adoption agreements, surrogacy contracts, and contracts between intimate partners—are another matter. Psychoanalysis invites us to examine the ways in which the prevailing free choice model fails to acknowledge the troubling influence of unconscious factors on the formation and breach of intimate contracts. As this chapter explains, psychoanalysis uncovers the subjective drama of intimate contracts: the role of fantasy and memory in constructing present reality; the need to replay and to master old traumas; the ambivalences, conflicts, and paradoxes of unconscious life. Psychological phenomena in the form of unconscious fantasy, transference, repression, attachment, regression, splitting, and resistance can color, distort, and undermine the parties’ decisions to enter into, and later abide by, intimate contracts in ways that go well beyond the ordinary commercial setting. By studying prenuptial agreements and surrogacy contracts carefully, this chapter sheds new light on the ways law can and should take psychoanalytic insights into account when regulating the formation and enforcement of these intimate agreements.