In the following article, we illustrate an interview between a living donor advocate and a potential living organ donor in which the donor faced a hard choice: the reasons to donate and the reasons not to donate were equally persuasive. In the discussion that follows, we analyze the act of willing, what differentiates coercion and willing, and how the case study highlights a different, but by no means rare, instance in which donors feel paralyzed by the choice at hand. In such cases, we suspect that donor advocates either do not approve the potential donor for transplantation or simply remain neutral. But we think that this approach benefits neither the donor nor the recipient. We conclude this study with recommendations for living donor advocates, providing questions that might solicit donors’ deeper values and suggesting that in these situations donors may benefit from additional time for reflection.