In an effort to improve our understanding of intellectual discussion in the undergraduate seminar and how it may be enhanced, three interdisciplinary discussion-based classes taken by primarily first-year students at a liberal arts college were studied ethnographically. Specifically, this article explores the struggles experienced by the students and professors, and the implicit ideals they held regarding the discussion in these seminars. Action-implicative discourse analysis of individual and group interviews revealed three situated problems: how to encourage participation amidst disengagement and dominance and support student risk-taking, how to teach the texts and have a sophisticated discussion that is student-driven, and how to have exciting intellectual discussions that are not "too emotional." These problems are each part of larger dilemmas including the desire for a supportive "and" challenging environment, the desire for coverage "and" openness, and the desire for emotional involvement and detachment.