This study focuses on D.H.Th. Vollenhoven and H. Dooyeweerd in the early years of their philosophical contact. We find that Dooyeweerd allied himself to Vollenhoven when working his way into philosophy. Vollenhoven’s “critical realism” at the time was their common ground. Towards the end of 1922 there are signs of new developments. Vollenhoven was motivated to purge realism of its latent scholastic features so as to express a clearer Calvinist-Scriptural position. Dooyeweerd in turn introduced into critical realism the perspective of eternity, as seat for the role of faith. From 1928 on, he traded critical realism in for transcendental criticism, the latter as guided by an intuitive viewing that takes place from the human being’s transcendent spiritual centre of personality. The discussion first clarifies what the initial critical realism of Vollenhoven was and that Dooyeweerd worked in its framework; then it highlights the diverging ways in which each moved away from that position.