Political dialogue among citizens offers numerous potential contributions to American politics, but attainment of these benefits hinges largely on the extent to which conversations cross lines of political difference. In what contexts are cross-cutting interactions most likely to thrive? Using data from five surveys, we find consistent evidence that the workplace is the social context best positioned to facilitate cross-cutting political discourse. Political discussion in the workplace involves a large number of discussants, and it involves greater exposure to people of dissimilar perspectives than does discussion in contexts such as the family, the neighborhood, or the voluntary association. We next consider whether workplace-based interactions are capable of producing beneficial effects. Despite the notoriously weak nature of work-based social ties, we find evidence that workplace-based exposure to differing political views increases people’s knowledge of rationales for political perspectives other than their own and also fosters political tolerance.