Wisdom, Hegel famously said, only flies at dusk. For many, the evening of the liberal-democratic nation state appears to be descending in a globalizing world. This disturbing prospect invites urgent reflection on which of the potentials of this fading order ought to be carried forward. In this climate of review and reassessment, discussions that had seemed done with re-surface sharpened by fresh purpose. The following paper attempts to put new light on a once vigorous dispute between Habermas and his post-modern critics over how best to weigh-up utopian energies at play in a liberal-democratic present. This was a contest distinguished by its all-or-nothing temper: either democratic Enlightenment with its commitment to rational solidarities or a Romantic enthusiasm for unreconciled particularities. I will argue that the stalemate between these two totalizing descriptions of the emancipatory potentials of modernizing processes needs to be unblocked and the debate put into motion once again. It will be argued that each offers a framework adequate to the description of only certain kinds of cultural needs. Alone, neither offers appropriate recognition of the ambiguous character of the distinctive hopes and expectations embedded in liberal democracies.