A cross-sectional study among 476 medical students in eastern Saudi Arabia investigated their interest in obstetrics and gynecology (OB/GYN) and the factors influencing this choice. Only 32.3% of students expressed an interest in this specialization, while the interest was significantly higher among women (19.2% chose it as their first choice) than among men (6.9%). Disinterest was significantly higher among men (87.4%) compared to women (57.8%). Interest increased with students' academic progress, with interns showing the highest share (21.8%). Factors such as clinical exposure, interaction with teachers, encouragement, and role models were more attractive to women, while men were discouraged by patient preferences for female doctors, cultural expectations, and concerns about the impact on family life. The study found that gender, academic performance, and institutional context were independently associated with OB/GYN career preference. Improving clinical exposure, mentoring, and changing cultural perceptions could help reduce gender gaps and improve recruitment to the specialty.