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The ability to choose emotion regulation strategies in accordance to contextual demands, known as emotion regulation flexibility, is key to healthy adaptation. While recent investigations on spontaneous emotion regulation choice tested the effects of emotional intensity and age using standardized negative pictures with no particular emotional quality, we elicited the discrete emotion of anger with personally relevant autobiographical memories in a sample of 52 younger and 41 older adults. In addition, we included habitual reappraisal as a predictor of emotion regulation choice. Our main hypothesis was that, compared with younger adults, older adults prefer less resource-demanding emotion regulation strategies (i.e., distraction) over more resource-demanding strategies (i.e., reappraisal), particularly if older adults' habitual reappraisal is low and the to-be-regulated anger is of high intensity. Surprisingly, our findings suggest that only older adults' emotion regulation choices depend on the emotional intensity of the autobiographical memory and habitual reappraisal. Only older adults with high habitual reappraisal preferred to reappraise their anger in situations of low anger intensity but switched to the less demanding strategy of distraction in high anger memories, indicating emotion regulation flexibility. This study extends previous research by testing emotion regulation choices in natural contexts and considering regulation habits. Although we replicate previous findings of emotion regulation flexibility according to emotional intensity in anger memories for older adults with high habitual reappraisal only, our findings illustrate the relevance of reappraisal habits to emotion regulation choice in age-comparative research. (PsycInfo Database Record (c) 2022 APA, all rights reserved).