Previous research has shown that after-work free-time activities can enhance employees’ work engagement and positively affect their general well-being and health. This study investigates whether the anticipation of an after-work free-time activity boosts employees’ work engagement. Building on the conservation of resources (COR) theory, we assumed that employees’ pleasant anticipation of an after-work free-time activity positively relates to work engagement within and between persons. Furthermore, we examined the moderating role of recovery-related self-efficacy (RRSE). In Study 1, 85 employees completed three questionnaires (morning, noon, and afternoon) on one workday, and we expanded the design to a one-week diary in Study 2 (N ¼ 56). Findings from (hierarchical) linear modeling supported the positive relationship between pleasant anticipation and work engagement between but not within persons. Moreover, RRSE was not found to be a moderator. Overall, our study demonstrated that employees vary in their pleasant anticipation, partly explaining differences in work engagement.