Do the presence of unfavorable contextual conditions shall realistically lead to a renunciation to fulfill the highest standards of deliberative democracy? Is the inevitable persistence of inter-group confrontation an insurmountable challenge? A cross-sectional assessment of opportunities and pitfalls in a culturally diverse set of eleven deeply divided countries present a burden of evidence against a naive expectation of translating deliberative models into them. However, this chapter describes a way in which legitimate factional claims might interweave with purely deliberative behavior in order to accommodate democratic confrontation without succumbing to patterns of unreasonable exchanges. Favorable conditions for this sort of confrontational deliberative democracy, at the institutional and citizen levels, are also specified.