Accumulating evidence suggests that dispositional optimism might be a protective factor against experiencing pain. The current paper presents two studies investigating the association between dispositional optimism and experimental pain. Moreover, the influence of pain-specific expectations on this association is investigated. In Study 1, mediation of pain-specific expectations in the relation between dispositional optimism and pain was hypothesized. Expected and experienced pain ratings were obtained from 66 healthy participants undergoing a cold pressor tolerance task. In Study 2, the moderating effect of dispositional optimism on the association between induced pain expectations and pain reports was studied in 60 healthy participants undergoing a 1-min cold pressor task. Both studies controlled for individual differences in fear of pain. Significant associations between dispositional optimism and pain ratings were found in both studies, although the exact time point of these associations differed. Subscale analyses revealed that only the pessimism subscale contributed significantly to these findings. We found no evidence for hypothesized mediation and moderation effects. Alternative explanations for the optimism-pain association are discussed.