Contrary to popular belief many choice options and the ability to reverse one's initial choice are sometimes associated with decreased chooser satisfaction. Two studies investigated the role of counterfactual thinking in explaining these paradoxes. Participants chose drawing implements from either a limited (6) or extensive (24) choice set (Study 1), or an expected reversible/non-reversible selection (Study 2). Following a drawing task, satisfaction with their chosen implement was rated under either high or low cognitive load to manipulate the availability of counterfactual alternatives. In Study 1 satisfaction was higher with limited vs. extensive choice under low load. The number of counterfactuals generated mediated this effect. Under high load the pattern was reversed. Participants in Study 2 generated more counterfactuals when reversibility was expected under low but not high load and this partially mediated the impact of expected reversibility on revealed satisfaction. Implications for theoretical understanding of these paradoxes are discussed.