How do people know what interacting with others would be like? This research examines how subjective feelings of difficulty in imagination can influence judgments in the context of social interaction. Participants imagined behaviors of members of a group while difficulty of imagination was manipulated, and reported outlook of future interactions with them. Study 1 revealed that after imagining target group members' reactions in situations that are inherently more difficult, participants had more negative outlook of future interaction with them. Perceived difficulty of imagination partly explained this effect. In Study 2, when incidentality of the association between the situations and the target group was made explicit, the outlook of future interaction with the targets was less negative. The findings extend research on metacognition to interpersonal context while offering several interesting contrasts with previous studies. Limitations and possible future directions are discussed.