How might frequent gamblers convince themselves to keep playing despite persistent losses or after a win that should be savored? The purpose of this research is to examine the unexplored question of how frequent gamblers’ use counterfactual thinking to motivate their desire to continue gambling. Using a sample of n = 69 high and n = 69 low frequency gamblers in a field setting, we found that infrequent gamblers tended to consider how the perceived outcome of losing “could have been better” (i.e., upward counterfactual thinking), and how a winning outcome “could have been worse” (i.e., downward counterfactual thinking). This pattern of counterfactual thinking is considered typical in many settings and may, in a gambling context, support a potentially more responsible approach by helping infrequent gamblers to learn from past mistakes to avoid significant future losses and to savor wins to protect returns gained. Alternatively, we found that frequent gamblers were more likely to generate ‘dual counterfactuals’ which include both upward and downward counterfactuals in response to losses and wins. We argue that this dual pattern of counterfactual thinking may allow frequent gamblers to more easily justify their desire to continue gambling. Findings suggest that challenging gamblers counterfactual thinking patterns could assist clinicians in moderating the potential for high-risk behaviors.