This study examined the relationship between social anxiety (SA) and the generation of upward counterfactual thoughts (U-CFT; ―if only...‖ thoughts imagining better outcomes to past events). U-CFT has been associated with negative affect and with social anxiety in past research (e.g., Kocovski et al., 2005). Participants (n= 89) were randomly assigned to generate U-CFT in response to a controllable or uncontrollable social-evaluative scenario. When comparing those with extreme SA scores, those higher in SA generated a greater number of upward as compared with downward CFTs. A significant positive correlation between SA and U-CFT was found when examining subsets of the sample (i.e., those in the controllable scenario, students). Potential mediators between SA and CFT were examined. Postevent Processing emerged as the only significant mediator (among students only). There was no evidence of maladaptive CFT (i.e., in response to the uncontrollable scenario only) within subsets or the sample as a whole.