This paper discusses some challenges for the design of sympathetic robots, including a lack of conceptual clarity and the difficulty of quantifying an instance of sympathy. Candace Clark’s sociological sympathy account is offered as a solid theoretical basis for advancing the design and acceptance of sympathetic robots. The aspects of her theory relevant to HRI and some potential challenges in its implementation are discussed, as well as the alarming potential for sympathetic robots to act ideologically imperialistic, or to ‘nudge’ users across cultural boundaries.