How do people inferentially evaluate others’ levels of intimacy with friends? We examined the inferential evaluation of intimacy based on the observation of interpersonal communication. In Experiment 1, participants (N = 41) responded to questions after observing conversations between friends. Results indicated that participants inferentially evaluated not only goodness of communication, but also intimacy between friends, using an expressivity heuristic approach. In Experiment 2, we investigated how inferential evaluation of intimacy was affected by prior information about relationships and by individual differences in face-to-face interactional ability. Participants (N = 64) were divided into prior- and no-prior-information groups and all performed the same task as in Experiment 1. Additionally, their interactional ability was assessed. In the prior-information group, individual differences had no effect on inferential evaluation of intimacy. On the other hand, in the no-prior-information group, face-to-face interactional ability partially influenced evaluations of intimacy. Finally, we discuss the fact that to understand one’s social environment, it is important to observe others’ interpersonal communications.