Objective: The aim of this study was to assess health insurance acquisition awareness, knowledge, and associated emotions among college students preparing to enter the workforce. Methods: A 21-item survey was developed to gather data on knowledge, awareness, and emotions associated with health insurance acquisition conversations with future employers. Results: Most respondents (91.1%), indicated they have thought about obtaining their own health insurance. The study found that participants rated acquiring health insurance more important the closer the respondent was to graduation; F[subscript 4,96] = 3.84, p = 0.006. An increase in stress emotions was indicated (F[subscript 4,96] =14.41, p = 0.000) and a reduction in positive emotions (F[subscript 4,96] = 2.99, p = 0.035) regarding health insurance acquisition post-graduation. Conclusions: College students identify low knowledge and indicate high levels of stress regarding health insurance conversations with future employers post-graduation. These findings are important for developing self-efficacy-based health education content preparing students for engaging in these conversations confidently and effectively.