This case study introduces “Rose” and “Michael,” a couple with infertility issues that may be related to Rose’s weight. The story details a visit to a pre-conception clinic and the struggle that Rose and Michael face in addressing underlying issues with adherence to clinic instructions. The case makes use of the five steps in the problem-solving process of design thinking as Rose and Michael progress through activities such as keeping a food record and a reflection diary, to navigating real life barriers to weight loss. Students assemble facts, synthesize information, and interpret behaviors during the sections of the case as they become familiar with terminology and techniques that impact a universal health issue of non-compliance, or as we find in the case, non-adherence. This case was developed for upper-level undergraduates and graduate students in a variety of health profession majors and would work well as part of an interdisciplinary class including social work, community health, health education, nursing, and dietetics.