Objective: Studies of health-related behaviors, including weight loss, have shown that risk of relapse decreases over time, although reasons for this relationship are unclear. The purpose of this cross-sectional study was to determine if subjects who have maintained weight losses for varying periods of time report different strategies for weight loss maintenance or differences in the effort and pleasure associated with weight maintenance behaviors. Research Methods and Procedures: Subjects were 758 women and 173 men who had maintained losses of at least 30 lb (mean = 60 lb) for 2 years or longer (mean = 6.8 ± 7.0 years). Self-administered questionnaires assessed subjects' use of weight maintenance strategies in the past year and their perceptions of the effort, attention, and pleasure associated with weight maintenance. Results: Subjects who had maintained weight losses longer used fewer weight maintenance strategies and reported that less effort was required to diet and maintain weight and that less attention was required to maintain weight. The pleasure derived from exercise, low-fat eating, and maintaining weight was unrelated to duration of weight loss maintenance. Discussion: As duration increases, a shift in the balance between the effort and pleasure of weight maintenance may occur. This shift may increase the likelihood of continued maintenance.