When is a question appropriate? In Recontextualizing Context, Fetzer (2004) distinguishes between “grammaticality” and “appropriateness” of sentences and utterances. Appropriateness, other than grammaticality, is a socio-cultural construct. Whereas the grammaticality of sentences may be judged without consideration of their textual, interpersonal, or interactional context, the appropriateness of utterances is highly context-dependent on all these levels. This is especially apparent in dialogical discourse types like media interviews. This contribution assumes as a working hypothesis that the appropriateness of questions can be approached through an analysis of the subsequent answers. Data is taken from videotaped interviews television journalists conducted with politicians and experts during British election night coverages. Their analysis is based on the pragmatic framework developed by Harris (1991) for the analysis of politicians’ evasiveness, and the multidisciplinary frameworks developed by Lauerbach (2003, 2004) and Becker (2005, 2007) for the analysis of interviewing practices. Comparison of interviews with politicians and interviews with experts reveals clear differences as to what answerers interpret as an appropriate question within the global context of the election night coverage and with respect to the question’s local textual, interpersonal, or interactional context.