Politics is a messy business. Filled with contradictory obligations, imperfect relationships, and uncertain outcomes, the very nature of politics ensures that its practitioners will face ethical challenges on an everyday basis. Despite this, literature exploring political dilemmas—mainly written in the Dirty Hands genre—has generally overlooked ethical dilemmas as politicians routinely face them in favor of dramatic dilemmas that few, if any, will ever wrestle with. In this article, I argue that detaching political dilemmas from political reality has been a mistake: that there is a need to rethink what political dilemmas are, what they could be, and what we can learn from studying them. Specifically, I argue that four aspects of political dilemmas as they are currently constructed should be rethought. First, conflicts between mutually exclusive ethical obligations should be considered an integral part of politics rather than as dramatic one-off events breaching the status quo. Second, what ethical principles are in politics, and why they are considered as such, should be explored in their own right rather than taken for granted. Third, political dilemmas should reflect the collective element of political decision-making: most, if not all, decisions in politics involve multiple actors and audiences. Fourth, political dilemmas should include enough relevant context to ensure that analyses and conclusions are drawn from similar premises. Rethinking these four aspects will bring political dilemmas closer to political reality, ensuring that normative, theoretical, and philosophical conclusions also can have practical relevance for politicians facing them—at least, so I will argue.