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Although we know quite a lot about the demographic sources of loneliness, little research has assessed the sources of loneliness that exist at the situational level of daily life. In this article, I analyze how the activity people engage in moderates the extent to which social isolation associates with feelings of loneliness. I propose that violating situational expectations is one possible source of loneliness, which leads to this article's hypothesis that social isolation will affect well-being most strongly when it occurs during normatively social activities (e.g., eating), relative to non-normatively social activities (e.g., traveling). Time-diary data collected from 627 graduate students show that being alone while engaging in normatively social activities tends to more strongly associate with a sense of loneliness than does being alone during non-normatively social activities. These results indicate that loneliness may be produced by multiple factors, including the context of a person's social isolation. This article concludes by discussing possible benefits of this research and future research plans.