In the present study we elucidate the emotional and executive control interactions that might underlie optimism and pessimism. Participants completed a self-report measure of optimism/pessimism and performed an emotion faces categorisation task and an emotion n-back task in which they indicated whether each of a series of faces had the same or a different emotional expression (happy, sad, neutral) as the face presented two trials before. Trials were structured to measure latency to update emotional content in working memory (WM). More pessimistic individuals formed connections among positive stimuli, and broke connections among positive and sad stimuli, in WM more slowly than did less pessimistic individuals; levels of optimism/pessimism did not affect the rate with which individuals formed and broke connections among neutral representations in WM. It appears, therefore, that levels of pessimism are related to specific affective cognitive mechanisms in WM that may be involved in emotion regulation.