An historical perspective on roleplaying and behavioral rehearsal procedures is presented, and its current application to assertiveness training is discussed. One drawback to traditional models of assertive-behavioral roleplaying is the slowness of progress which results from client's unresolved ambivalence about assertiveness. Many clients fear that any deviation from one behavioral extreme (unassertive or aggressive) will result in the opposite extreme behavior. An insight-oriented model of roleplaying (i.e., the method of contrasted roleplays) is presented in which the three successive roleplays (unassertive, aggressive and assertive) facilitate client resolution of ambivalence about assertiveness. Implicit in this model is the assumption that change towards increased assertiveness is more likely to occur when clients can realistically assess the breadth of behavioral possibilities open to them between the extremes of unassertive and aggressive behavior. The social consequences of acting out either extreme are explored and in the process constructive assertive alternatives are developed which integrate both the task and feelings. This model defines assertiveness as a broad middleground of behavioral alternatives, and acknowledges the validity of both the internal experience of powerful negative emotions and the realistic social constraints effecting the full expression of these feelings. The method of contrasted roleplays is described in detail, with representative transcripts.