This paper argues that the apparent divide between Cognitive Behavioural Therapy (CBT) and Existential-Phenomenological Therapy (EPT) stems less from technique than from their differing philosophical foundations—specifically, objectivist versus contextualist epistemologies. While both approaches aim to help clients tolerate uncertainty and move toward meaningful change, CBT traditionally presumes a singular rational truth, pathologising beliefs that deviate from it. In contrast, EPT—and third-wave CBT approaches like Acceptance and Commitment Therapy (ACT)—adopt a contextualist stance, viewing beliefs within the personal, historical, and relational world of the client. The paper examines how absolutist core beliefs function to deny uncertainty and preserve psychic coherence, and how therapists' philosophical positioning affects the use of Socratic questioning. An objectivist stance may covertly impose the therapist’s framework, while contextualism enables genuine therapeutic inquiry and client-led meaning-making. Drawing on examples and case material, the paper shows that enduring change does not arise from rational disputation but from cultivating openness to experience and flexibility in relating to thoughts. Ultimately, it calls for greater philosophical self-awareness in practice, arguing that bridging CBT and EPT requires therapists to move beyond technical integration and reckon with their underlying worldviews.