There has been a resurgence of interest in the work of Raya Dunayevskaya and Herbert Marcuse, particularly regarding their shared concern with humanism and dialectics. Recent edited collections on Dunayevskaya’s correspondence have, however, drawn a sharp contrast between the conceptions of the dialectical method: Dunayesvkaya, who emphasized the need for ‘philosophic new beginnings’ to offer a new relationship between theory and practice, and Herbert Marcuse who, despite his piercing identification of the one-dimensionality of late capitalism, continued with a problematic basis in (orthodox) Marxist categories. In this review essay, we outline the latest of these two volumes and its distinct contributions before engaging in a critique of Marcuse’s restrictions on humanism and dialectics, via a comparison with Dunayevskaya’s dialectical approach that was premised on questioning ‘the problems of the age’ and emphasized the open and negative polarity of dialectical possibilities.