Psychoanalysis is usually thought of as a context in which people who are patients have the maximum amount of expressive freedom. One way of thinking of the fundamental rule of psychoanalysis, the injunction to free association, is as the throwing off limitations on self-expression. But I argue that, somewhat surprisingly, psychoanalysis in general, and free association in particular, bring their own forms of expressive limitations. I consider a few different ways of understanding free association through the lenses of speech act theory and Gricean conversational analysis to highlight these limitations that patients must struggle with, and against.