Abstract Background: The current medical curriculum for both undergraduates and postgraduates is deficient as it does not address the relevant aspects resulting in incomplete training and avoidance of asking about sexual health in routine clinical practice. This research studied the existing knowledge and comfort while taking sexual history, as well as managing the sex-related problems in patients by the medical postgraduates. Methods: Two hundred medical residents were recruited in the study after informed consent and ethics approval. Residents in I/II/III years in clinical and nonclinical disciplines were enrolled after systematic sampling. A semi-structured pro forma was used to collect information on knowledge, comfort, and training in sexual health with the help of open and closed-ended questions. Results: All knew about menstrual and reproductive health, 70% had knowledge about anatomy and sexual response cycle, 40% about sexual dysfunctions or its treatment. 76% expressed no adequate training was given and 96% felt that the lectures on sexual medicine were less useful. Ninety-one percent wanted training using videotapes, role plays, and group discussions. Sixty-eight percent were comfortable talking about sexual problems to patients of the same sex and 27% to the opposite sex. Ninety-eight percent gave the inability to maintain privacy and confidentiality while sexual history taking in both outpatient and indoor settings. Conclusions: Our study has highlighted some of the existing lacunae in the current Indian educational system with regard to sexual health, the existing knowledge and comfort of the postgraduates. More studies and research should be conducted to support the evidence. Curriculum changes with importance to sexual health and increased training can further be considered.