Background: Little is known about the characteristics of mentoring relationships formed between faculty and medical students. Individual mentoring relationships of clinical medical students at Munich Medical School were characterized quantitatively and qualitatively. Methods: All students signing up for the mentoring program responded to a questionnaire on their expectations (n = 534). Mentees were asked to give feedback after each of their one-on-one meetings (n = 203). A detailed analysis of the overall mentoring process and its characteristics was performed. For qualitative text analysis, free-text items were analyzed and categorized by two investigators. Quantitative analysis was performed using descriptive statistics and Wilcoxon-test to assess differences in grades between students with and without mentors. Results: High-performing students were significantly more likely to participate in the mentoring program (p<0.001). Topics primarily discussed include the mentee's personal goals (65.5%), career planning (59.6%), and experiences abroad (57.6%). Mentees mostly perceived their mentors as counselors (88.9%), providers of ideas (85.0%), and role models (73.3%). Mentees emphasized the positive impact of the mentoring relationship on career planning (77.2%) and research (75.0%). Conclusions: Medical students with strong academic performance as defined by their grades are more likely to participate in formal mentoring programs. Mentoring relationships between faculty and medical students are perceived as a mutually satisfying and effective instrument for key issues in medical students' professional development. Practical implications: Mentoring relationships are a highly effective means of enhancing the bidirectional flow of information between faculty and medical students. A mentoring program can thus establish a feedback loop enabling the educational institution to swiftly identify and address issues of medical students.