The motives, strategies, and effectiveness of emotion regulation have been the focus of emotion regulation literature to date. However, naturalistic research finds that individuals choose not to regulate their emotions as often as they choose to regulate them. We examined how often people did not regulate their emotions, the reasons why people chose not to regulate, and contextual factors related to not regulating. Adults (N = 179; Mage = 35.34, SDage = 12.26) completed ecological momentary assessments five times daily for 14 days, reporting on their largest emotional shift over the last three hours, contextual factors regarding this shift, and emotion regulation. When participants indicated not regulating, they reported their reasons for not regulating. People reported not regulating about half the time; the most frequent reasons were that emotions were appropriate or helpful (39%) or not intense enough (31%). The likelihood of not regulating was associated with greater situational pleasantness, lower situational importance, more positive affect, and less negative affect. People were less likely to regulate when alone. This research focused on an overlooked but significant part of the emotion regulation process, choosing not to engage in emotion regulation. Findings clarify the reasons people do not regulate as well as contextual features related to their decision.