We address two key research questions. First, is there an association between parental separation and living with a stepparent in childhood and maladjustment in adulthood? Second, we examine the role conflict plays in these associations. We study whether parental union dissolution is only detrimental in cases of heightened post-divorce interparental conflict. We build upon this “good divorce” hypothesis by considering whether the possible association between living in a stepfamily and depressive symptomatology is only present in cases of high stepparent-child conflict (a “good stepparent” hypothesis). Using data from the OKiN survey (Parents and Children in the Netherlands), we analyze the self-reported depressive feelings of Dutch adults aged 25–35. Of our sample, 2233 adults experienced parental separation in childhood (on average, 22 years before data collection); of those, n = 1665 had lived with a stepparent. Our findings clearly indicate that having experienced parental divorce is associated with an increase in depressive symptoms only for those adults who were exposed to heightened post-divorce interparental conflict. Similarly, living with a stepparent is linked to maladjustment only in cases of high stepparent-child conflict. Importantly, we find evidence that a low-conflict stepfather-child tie could even buffer against maladjustment (which is not the case for a low-conflict stepmother-child tie).