Postpartum mothers have to decide whether to leave the workforce for some time and, if so, when to return to paid work. Two kinds of regrets might evolve as a result of women's leave‐related decisions: stay‐at‐home and return‐to‐work regrets. The present research investigates how these forms of regrets are associated with women's affective organizational commitment. We conducted a four‐wave longitudinal study with female participants mostly living in Switzerland (61%) and Germany (37%). The first measurement occasion took place during pregnancy (N = 294), and the subsequent three postnatal measurement points were at 6 (n = 281), 12 (n = 254), and 24 months (n = 230) after childbirth. As expected, higher organizational commitment during pregnancy predicted stronger stay‐at‐home regrets. By contrast, women's prenatal organizational commitment did not turn out to be predictive for lowered return‐to‐work regrets. We further assumed cross‐lagged associations between post‐birth organizational commitment and return‐to‐work regrets. Our results suggest that return‐to‐work regrets are predictive of decreases in affective organizational commitment. Reversed causation, that is, effects from postnatal organizational commitment to return‐to‐work regrets, could not be confirmed. Results are discussed regarding theoretical, methodological, and practical implications.