A person's well-being depends heavily on forming and maintaining positive relationships, but people can be reluctant to connect in ways that would create or strengthen relationships. Emerging research suggests that miscalibrated social cognition may create psychological barriers to connecting with others more often. Specifically, people may underestimate how positively others will respond to their own sociality across a variety of social actions, including engaging in conversation, expressing appreciation, and performing acts of kindness. We suggest that these miscalibrated expectations are created and maintained by at least three mechanisms: differential construal, uncertain responsiveness, and asymmetric learning. Underestimating the positive consequences of social engagement could make people less social than would be optimal for both their own and others' well-being.