Many have claimed that legitimate constitutional democracy is either conceptually or practically impossible, given infinite regress paradoxes deriving from the requirement of simultaneously democratic and constitutional origins for legitimate government. This paper first critically investigates prominent conceptual and practical bootstrapping objections advanced by Barnett and Michelman. It then argues that the real conceptual root of such bootstrapping objections is not any specific substantive account of legitimacy makers, such as consent or democratic endorsement, but a particular conception of the logic of normative standards—the determinate threshold conception—that the critic attributes to the putatively undermined account of legitimacy. The paper further claims that when we abandon threshold conceptions of the logic of legitimacy in favor of regulative-ideal conceptions, then the objections, from bootstrapping paradoxes to the very idea of constitutional democracy, disappear. It concludes with considerations in favor of adopting a more demanding conception of the regulative ideal of constitutional democracy, advanced by Habermas, focusing on potentials for developmental learning.