Spending time with others affords numerous benefits. One way a person can spend time with others is through a self-invitation—asking to join the plans of others. We address the psychological processes involved with self-invitations to everyday social activities from both the self-inviter’s perspective and the perspective of those with the plans (“plan-holders”). Across eight studies (seven preregistered), we demonstrate that potential self-inviters fail to ask to join the plans of others as often as plan-holders would prefer, because potential self-inviters overestimate how irritated plan-holders would be by such self-invitations. Further, we show that these asymmetries are rooted in differing viewpoints about the mindsets of plan-holders when they originally made the plans. Namely, potential self-inviters exaggerate the likelihood that plan-holders had already considered inviting them but decided against it (vs. made plans without considering inviting them). We conclude by discussing the various implications of our findings.