Objectives: To identify the role of mentorship and other factors associated with obstetrics and gynecology (OB/GYN) resident interest in pursuing a fellowship in gynecologic oncology. Methods: A survey link was emailed to U.S. OB/GYN residency program coordinators to disperse to current residents. The 80-item survey asked about plans to pursue fellowship and influencing factors. Participants were stratified based on decision to pursue a fellowship in gynecologic oncology. Student's t-test and Mann-Whitney tests were applied. Results: Among 236 surveyed residents, 32 (13.6%) were planning to pursue a fellowship in gynecologic oncology. There were no demographic differences favoring the choice of gynecologic oncology; however, trainees at academic programs were more likely to aspire to the subspecialty (p = 0.01). Residents interested in gynecologic oncology had marginally more mentors than others (p = 0.06), were more likely to have a gynecologic oncology mentor (p < 0.01), and were more likely to have cited mentorship as a reason for their career aspirations (p = 0.01). These residents were also less likely to report obvious burnout among faculty and fellows in their department (p < 0.01 and p = 0.01, respectively). Conclusions: Strong mentor relationships and the display of job satisfaction and work-life balance influence OB/GYN residents’ interest in gynecologic oncology fellowships. Programs should consider formal mentorship programs for residents, with priority on matching by subspecialty. The value of fellow and faculty efforts in mentorship should be recognized, and appropriate time should be protected for these relationships, along with efforts to support fellows and faculty at risk for burnout.