In previous research, older adults show greater emotional benefits from distracting themselves than from reappraising an event when strategically regulating emotion. Older adults also demonstrate an attentional preference to avoid, while younger adults show a bias toward approaching negative stimuli. This suggests a possible age-related differentiation of cognitive effort across approach and avoidance of negative stimuli during emotion regulation. In this study, we tracked cognitive effort via pupil dilation during the use of distraction (avoidance) and reappraisal (approach) strategies across age. Forty-eight younger adults (M = 20.94, SD = 1.78; 19 men) and 48 older adults (M = 68.82, SD = 5.40; 15 men) viewed a slideshow of negative images and were instructed to distract, reappraise, or passively view each image. Older adults showed greater pupil dilation during reappraisal than distraction, but younger adults displayed no difference between conditions—an effect that survived when controlling for gaze patterns. Gaze findings revealed that older adults looked less within images during active emotion regulation compared with passive viewing (no difference between distraction and reappraisal), and younger adults showed no difference across strategies. Younger adults gazed less within the most emotional image areas during distraction, but this did not significantly contribute to pupil response. Our findings support that distraction is less cognitively effortful than reinterpreting negative information in later life. These findings could be explained by older adults’ motivational bias to disengage from negative information because of the age-related positivity effect, or compensation for decreased working memory resources across the life span.