When people encounter others surpassing them in terms of an important quality, possession, or achievement, they often think about what might have happened differently so that they would have obtained a better outcome. Such upward counterfactual thoughts have been shown to contribute to the intensity of envy. We investigated whether specific counterfactual thoughts distinguish different forms of envy, namely benign envy, which entails upward motivation, and malicious envy—which entails hostility. A meta-analysis of 8 studies (1 preregistered, N = 1,264) of a first line of research supports that recalled episodes of benign versus malicious envy are characterized by more additive, self-focused counterfactuals or by more other-focused counterfactuals, respectively. Furthermore, a meta-analysis of 6 studies (1 preregistered, N = 1,299) of a second line of research supports that eliciting these counterfactuals promotes the corresponding form of envy. In line with functional accounts of counterfactual thinking and envy, the results highlight cognitive processes that underlie functionally diverging pathways of envious responding. (PsycInfo Database Record (c) 2021 APA, all rights reserved)