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To understand the characteristics and career goals of medical students selecting a career in obstetrics and gynecology.In 2015–2016, medical students invited for interviews for obstetrics and gynecology residency at the University of Colorado, University of Washington, University of California San Francisco, Loyola University, and New York University received a voluntary 20-item electronic survey regarding factors influencing their choice of medical specialty.Two hundred twenty-six of 356 students responded (63%). Mean age was 27 years, and 88% (n=199) were women. General surgery was the most common alternate specialty (36%, n=81). The most commonly cited drawback to obstetrics and gynecology was “long hours” (66%, n=148). After residency, 157 (70%) applicants planned to complete fellowship training, 127 (56%) pursue international work, 156 (69%) seek an academic position, and 207 (92%) practice in an urban setting. One hundred twenty-four applicants (55%) planned to work 51–60 hours per week and 111 (49%) planned to take 2–3 nights of call per month. Two thirds (n=150) predicted they will have greater than $100,000 educational debt on graduation.Contemporary residency applicants have high educational debt and disproportionately plan to pursue fellowship, international work, careers in academic medicine, and work in urban centers. Based on the projected career plans among obstetrics and gynecology applicants, the workforce needs of the population may not be met.