Objective: Pain following the insertion of separators and archwires varies with age, sex, race, ethnicity, threshold, and health status. This study aimed to evaluate the characteristics of pain in orthodontic patients after the insertion of elastomeric separators, its effects on daily life, and its association with age and sex in a population not previously studied in this regard. Methods: A crosssectional study of 130 patients undergoing orthodontic treatment included collecting data on demographics, pain experienced following the placement of separators, time of onset, duration, characteristics, change in dietary pattern or chewing side, intake of analgesics, and severity of pain on the Wong Baker’s scale. The results are reported as counts and percentages. Associations between sex and age were evaluated using Pearson’s chi-square test. Results: Among the 130 patients, 56.2% were 9–20 years old, 63.8% experienced pain following the insertion of separators, 22.9% had their first episode of pain at 4 hours, 56.6% experienced intermittent pain, and 37.3% experienced discomfort; 18.1% males and 81.9% females experienced pain following the insertion of separators.Pearson’s chi-square test showed a significant association between pain and sex (P = 0.04). Most patients (37.3%) reported “hurts little more” for pain intensity on Wong Baker’s scale and 21.7% reported all four quadrants as sites of pain. Conclusions The pain experienced after separator insertion was associated with sex and age. Females experienced more pain than males and patients between the age range of 21 and 36 years suffered more pain during mastication than between 9 and 20 years old.