Engineering and design students are often required to evaluate their products against user requirements, but frequently, these requirements are abstracted from the user or context of use rather than coming from actual user and context data. Abstraction of user requirements makes it difficult for students to empathize with the eventual user of the product or system they are designing. In previous research, Design Heuristics have been shown to encourage exploration of design solutions spaces at the initial stages of design processes. This study combines use of Design Heuristics in an engineering classroom context with a method designed to connect students with an understanding the context of the user, product use setting, and sociocultural milieu. We adapted an existing method, the cognitive walkthrough, for use in an engineering education context, renaming it the empathic walkthrough. In this study, this method was revised and extended to maximize empathy with the end user and context, using these insights to promote a more situated form of idea development using the Design Heuristics cards. We present several case studies of students using this method to expand their notion of situated use, demonstrating how this method may have utility for importation into engineering contexts. Our early testing has indicated that this method stimulates empathy on the part of the student for the design context within which they are working, resulting in a richer narrative that foregrounds problems that a user might encounter.