Objectives <p>The Bipolar Continuum Hypothesis suggests that compassionate self-responding (CS) and uncompassionate self-responding (UCS) operate as opposing ends of a dynamic continuum. While this aligns with the view of self-compassion as a synergistic system, some researchers argue CS and UCS may function independently, raising questions about their relationship. This study examined real-time fluctuations in CS and UCS in response to contextual factors, addressing these theoretical and methodological complexities.</p> Methods <p>Across two longitudinal field studies (Study 1, <i>n</i> = 326; Study 2, <i>n</i> = 168), 494 participants provided weekly Ecological Momentary Assessment (EMA) data over 3 months. We assessed how immediate emotional states, decentering (a mindfulness-related skill), and event unpleasantness influenced CS and UCS in daily life.</p> Results <p>Partial support was found for the Bipolar Continuum Hypothesis, with CS and UCS generally showing inverse fluctuations in response to negative affect and decentering. Negative affect was the strongest predictor, linked to higher UCS and lower CS. Decentering showed a stronger association with reducing UCS than increasing CS, suggesting an asymmetry in their interaction. An idionomic analysis revealed individual variability, with a subset of participants displaying no clear inverse relationship, or even a positive association, between CS and UCS. Event unpleasantness had a minor impact.</p> Conclusions <p>These findings partially support the Bipolar Continuum Hypothesis, particularly regarding responses to emotional states, while also highlighting individual differences. Future research could explore the potential benefits of refining interventions and tailoring approaches to account for individual variations in CS and UCS dynamics.</p> Preregistration <p>This study is not preregistered.</p>