The present study examined life stage and cultural differences in the degree to which familiarity of one's physical location and interaction partner is associated with daily well-being. Participants reported all the activities they engaged in and how they felt during these activities on a previous day using the Day Reconstruction Method (Kahneman, Krueger, Schkade, Schwarz, & Stone, 2004). Both Korean and American retirees were happier when in a familiar place than in an unfamiliar place, whereas the reverse was true for both Korean and American working adults. In addition, we found cultural differences in the role of familiarity of the interaction partner. Specifically, Koreans (both retirees and working adults) were substantially happier when they interacted with a familiar person than when they interacted with an unfamiliar person. In contrast, Americans (both retirees and working adults) were no happier with a familiar person than with an unfamiliar person.