The importance of mentorship in medicine has been established. However, little is known regarding the influence of mentors in orthopedic surgery. This study sought to (1) determine the prevalence of mentoring relationships in orthopedic surgery, (2) assess the influence of mentors in specialty and subspecialty selection, and (3) evaluate the importance of gender in orthopedic mentoring relationships. An electronic survey was distributed to 358 orthopedic surgeons at academic residency programs. Participants were asked to report mentoring relationships and their attitudes toward mentors, including gender preferences. A total of 117 (95 males and 22 females) surveys were returned. The majority of respondents (66.7%, n=78) had at least one mentor in their career, and the majority of respondents (66.7%, n=52) were satisfied with their mentoring experience. Residency was the most common time to have a mentor, and 73.3% (n=44) of respondents indicated their mentor was influential in determining their subspecialty. Although only 50% of respondents indicated they had a mentor in medical school, 84.2% (n=32) believed their mentor was influential in selecting an orthopedic surgery residency. The majority (79.4%, n=62) of respondents did not have a preference on the gender of their mentor. Many orthopedic surgeons have a mentor at some point in their career who influenced their specialty or subspecialty decision. Mentoring experiences are less prevalent in medical school, and female medical students may lack accessibility to mentoring opportunities. Future efforts should focus on opportunities that connect medical students to orthopedic surgery faculty to further diversify the field and close the gender gap. [Orthopedics. 2020; 43(1):e37-e42.].