Objectives Most studies of emotion regulation across the lifespan have focused on how individuals manage their emotions during or after emotional events. However the current study examined how anticipatory emotion regulation behavior, a process that occurs before an emotional event has been experienced, influenced young (Mage = 19.66) and older (Mage = 70.02) adults’ affective experience, physiological reactivity, and task performance. Method Participants were first provided with a detailed description of an upcoming evaluative stress task, but were able to regulate their affective state by selecting one video to watch from a selection of 8 videos labelled by valence and arousal before completing the stressful task. Results Participants across age groups were more likely to select a positive video, and participants who made positive selections initially felt better than those who selected negative content, though they experienced sharper mood declines than those who selected a negative video. Negative selections were linked to better performance on the speech task across age groups. Conclusions These findings suggest that, when anticipating a negative situation, participants preemptively increase positive emotions. However, while positive selections served to temporarily improve mood, the effects did not last throughout the stress task. These results provide more evidence for age similarity than age differences in anticipatory emotion regulation effects and behaviors.