Free association allows the emergence of novel formulations about self and, along with them, new insights, but it needs to modulate the risks of chaos and the compromising of mental integrity on the one hand and the arrest of growth on the other. Interpretation acts to contain and hold associative pressures and so helps maintain the patient's mental integrity, but it limits associative freedom by being necessarily inferential. In addition, in current interpretative strategies, analytic progress depends on the patient's ability to associate. This ability may be poor for longer or shorter periods during analysis. To help resolve these difficulties, a strategy of associative dialogue is proposed and clinically illustrated. The proposed strategy draws on the associative abilities of the analyst. This paper elaborates the way in which two basic forms of associative dialogue—bold and focused analysis—may facilitate the negotiation between freedom and continuity in analytic discourse.