Previous research has found that people consult closeness or proximity cues when they evaluate the plausibility or likelihood of a counterfactual alternative to reality. In this paper we asked whether the plausibility of counterfactuals extends to dynamic proximity cues that signal a sense of propensity or acceleration in the lead-up to an outcome. Subjects gambled on obtaining either three heads or three tails from three coin-flips. When they lost the gamble they thought it was more likely that they could have won if they had lost on the third coin-flip that was revealed rather than the first or second coin-flip. We discuss how the sense of propensity was raised prior to the revelation of the final decisive losing coin-flip which created a perception of psychological momentum towards winning. Moreover, the consequence of this propensity effect was to positively bias perceptions of the likelihood of the counterfactual winning outcome.