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The goal of this study was to identify factors associated with pain sensitivity, procedural discomfort, and referral for surgical hysteroscopy, aiming to improve office hysteroscopy success rates. This was an observational prospective cross-sectional study that analyzed data from women who underwent outpatient hysteroscopy between October 2022 and October 2023. Epidemiological, clinical, and procedural data were collected from medical records. Pain levels were assessed using a visual analog scale (VAS), categorized as acceptable (0–6) or severe (7–10). Statistical analyses were performed to explore associations between patient characteristics and pain levels, with p-values < 0.05 considered significant. This study evaluated 1662 women. The mean age was 54.0 (±12.4) years, and 59.1% were postmenopausal. Nulliparity, menopause, lower body mass index (BMI), and fewer vaginal deliveries were associated with higher pain levels (p < 0.05). Cervical stenosis significantly increased procedural pain: 20.8% and 27.6% of patients with stenosis resolved during the procedure, respectively, reported severe pain. In the multivariate logistic regression analysis, protective factors against severe pain included having ≥2 vaginal deliveries (OR 0.53, 95% CI 0.39–0.72), patent internal (OR 0.53, 95% CI 0.38–0.75) and external cervical orifices (OR 0.47, 95% CI 0.30–0.72), presence of myomas (OR 0.53, 95% CI 0.34–0.83), and biopsy performance (OR 0.55, 95% CI 0.41–0.74). Severe pain, uterine lesions, and stenosis were the main reasons for surgical referral. Lower BMI, nulliparity, menopause, and cervical stenosis were significant predictors of increased pain during outpatient hysteroscopy. These findings may help identify patients at higher risk for procedural discomfort and support strategies to improve success of office hysteroscopy.