A successful conversation requires participants to have knowledge of both the topic under discussion and the nature of conversation. This study asks whether people who are more sophisticated in their representation of conversation behave differently than their less sophisticated counterparts. This issue was probed by devising two operationalizations of what we call Conversational complexity. The two measures assessed peoples' constructs about conversation (operationalized by a measure of construct differentiation) and the manner in which people psychologically structure conversations (via a sorting task tapping the degree to which they focus on the surface features, or deeper structures, of conversations). Individuals who completed the two measures of complexity also participated in conversations and completed a number of personality indices. Each operationalization of conversational complexity was positively correlated with a variety of conversational involvement behaviors, measures of conversational enjoyment and person complexity, and memory for the interactions. Generally speaking, effective interactants who enjoyed conversations and recalled them well tended to have more constructs about conversations and psychologically represented conversations at a deeper level than their counterparts.