The experience of chronic loneliness has been associated with poorer physical health and well-being, including declines in cardiovascular health and higher levels of distressed affect. Given the long-term effects of loneliness on health and well-being, much research has focused on loneliness in older age. The purpose of the current study was to obtain a more detailed picture of the experience of loneliness in midlife and older adulthood by incorporating the context of a day's activities. We use a modified day reconstruction task to examine the activities in which middle-age and older adults engaged, the amount of time they spent alone, and the emotions experienced while engaging in a day's activities. Lonely individuals did not participate in different daily activities or spend more time alone during the day; however, loneliness was associated with engaging in more activities alone than with others. In regards to emotional experiences, daily activities yield a different profile of positive emotional experiences for lonelier individuals. The social context of daily activities was an important factor in understanding the effects of loneliness on experienced negative emotions. The results of this study provide insight into the influence of loneliness on the structure of a day and context for understanding the emotional experiences of lonely older adults.