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This longitudinal study was designed to examine the importance of social comparisons for coping with regret among young and older adults. It was expected that making downward social comparisons would be associated with a greater reduction in regret intensity over time among older, compared with young, adults. A total of 104 participants took part in this 4-month longitudinal study. The findings suggest that across different comparison targets, making downward (relative to upward) social comparisons was consistently related to reduced regret intensity over time among older adults. Among young adults, making downward social comparisons with personally known others, as opposed to age peers, was associated with lower regret intensity. In addition, older adults increased their reliance on downward social comparisons over time. This age-differential shift toward downward social comparisons further explained age differences in changes of regret intensity over time. Finally, differences in opportunities to undo regrets explained some of the age differences in the use and adaptive value of downward social comparisons. The implications of the findings for understanding and examining pathways to successful development are discussed.