Although decades of research show that people tend to see themselves in the best possible light, we present evidence that people have a surprisingly grim outlook on their social lives. In 11 studies (N = 3,293; including 3 preregistered), we find that most people think that others lead richer and more active social lives than they do themselves. We show that this bias holds across multiple populations (college students, MTurk respondents, shoppers at a local mall, and participants from a large, income-stratified online panel), correlates strongly with well-being, and is particularly acute for social activities (e.g., the number of parties one attends or proximity to the “inner circle” of one’s social sphere). We argue that this pessimistic bias stems from the fact that trendsetters and socialites come most easily to mind as a standard of comparison and show that reducing the availability of extremely social people eliminates this bias. We conclude by discussing implications for research on social comparison and self-enhancement.