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Studies suggest widespread advantages to peer mentoring programs; however, there is minimal data pertaining to medical students mentoring undergraduate students.To determine the feasibility and perceived effectiveness of a medical student-undergraduate student peer mentorship program.A needs assessment guided the development of Pre-Med Pair Up, a program connecting medical student mentors from the Medical College of Wisconsin and other US medical schools to undergraduates at Marquette University and the University of Wisconsin-Oshkosh to provide peer mentorship, premedical resources, and global health information. After 6 months, surveys were distributed to 43 premedical and 26 medical students to evaluate the program. Descriptive statistics and Pearson correlations (Eleven undergraduate and 26 medical students completed surveys. Most undergraduates expressed increased confidence in abilities as premedical students associated with program involvement (18.2% great, 27.3% moderate, 45.5% minimal, 9.1% no improvement). Increased confidence was strongly correlated with knowledge of volunteer opportunities (While self-reported confidence improved and overall positive program outcomes were statistically significant, the number of participants was low and the number who completed mid-year surveys was even lower. Therefore, no conclusions about program effectiveness were made. Instead, a lessons-learned approach was used to discuss the pilot development, implementation, and suggestions for future program installment.