Libertarian paternalism is “the set of interventions aimed at overcoming the unavoidable cognitive biases and decisional inadequacies of an individual by exploiting them in such a way as to influence her decisions (in an easily reversible manner) towards choices that she herself would make if she had at her disposal unlimited time and information and the analytic abilities of a decision-maker.” Hence, the rationale behind libertarian paternalism is pragmatic rather than purely academic. Libertarian paternalism seemingly operates under the banner of freedom. However, it fails to make its (metaphysical) presuppositions explicit, some of which are problematic. Particular attention should be paid to libertarian paternalism’s endorsement of a “two selves” picture of human rationality. This picture is fundamentally mistaken and leads to a misconception of freedom. A non-dualist account of freedom that has been formulated by Saint Anselm of Canterbury (1033–1109) could offer a way out of this conundrum.