Introduction: The purpose of this study was to evaluate the influence generational categories may have on commonalities among pharmacy students and their pharmacist preceptors during advanced pharmacy practice experiences (APPEs). Methods: Multiple-choice surveys aimed at evaluating generational characteristics were sent to pharmacy students and their preceptors during the first three APPEs. Questions focused on six key areas: preferred learning/teaching style, view of career/work, communication style, view of technology, life outlook, and personal characteristics. Each response corresponded to a generational category (Veteran, Baby Boomer, Generation X, Millennial). Students and preceptors were instructed to apply each question to themselves; students then applied each question to their preceptor, while preceptors applied the questions to students. Results: Twenty-six percent of students and 35% of preceptors completed at least one generational survey. Students selected the option that corresponded to their actual generational category significantly more often compared to preceptors (2.133 +/- 0.815 vs. 1.632 +/- 1.132, p = 0.007). Although none of the respondents belonged to the Veteran category, responses corresponding to this generation represented the second highest number of responses selected by students and preceptors alike. Conclusions: Students and preceptors identified with characteristics outside their actual generational category. In addition, both groups selected options such as working to make a difference that may correlate more with people who have chosen pharmacy as a profession. Pharmacist awareness of generational similarities may lead to a more successful student-preceptor relationship.