In this paper, I argue that David Lewis’s possible world semantics for counterfactual discourse and for fictional discourse are apparently inconsistent and in need of revision. The problem emerges for Lewis’s account once one considers how to evaluate ambifictional counterfactuals. Since this is likely not a concept familiar to most, and since it does not appear that the problem has been previously recognized in the critical literature, I will begin by rehearsing Lewis’s possible worlds semantics for counterfactuals and fiction. Then (...) I will explicate the distinction between intrafictional, extrafictional, interfictional, and ambifictional propositions. Next, I will state what an ambifictional counterfactual proposition is, and explain why this kind of discourse confounds Lewis’s system. I will conclude, finally, with a brief discussion of how the Lewisian would be best advised to resolve the paradox. (shrink)