Because of counterfactual comparisons, good outcomes that could have been better (i.e., disappointing wins) and bad outcomes that could have been worse (i.e., relieving losses) elicit relatively middling ratings on bipolar emotion scales. We conducted two experiments with gambles to examine whether such outcomes elicit neutral emotions, sequentially mixed emotions of positive and negative affect, or simultaneously mixed emotions. In Experiment 1, static unipolar measures of positive and negative affect revealed that disappointing wins and relieving losses elicit mixed emotions, rather than relatively neutral emotions. In Experiment 2, participants provided continuous unipolar measures of positive and negative affect by pressing one button whenever they felt good and another button whenever they felt bad. Results revealed that disappointing wins and relieving losses elicit positive and negative affect simultaneously, rather than in alternation.