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To minimize the possibility of experiencing regret over the outcome of a decision, people take into account their anticipated regret when evaluating their options before making the decision. The present study examined the accuracy of regret anticipation in the context of gambling behavior. Using a sample of 82 community gamblers, the study tested whether the gap between anticipated and actual regret is different for social gamblers (n=42) and problem gamblers (n=40). The effects of mood (frustrated and neutral) and selected personality factors (i.e., impulsivity, risk-taking, competitiveness) on the anticipation of regret were also investigated. The results revealed that problem gamblers committed a larger error in predicting regret than social gamblers. Frustrated mood was found to affect the anticipation error of social but not of problem gamblers. The role of inaccurately anticipated regret as a possible contributor to excessive gambling and its implications for the treatment of pathological gambling are discussed.