This cross-sectional study investigated the factors affecting pain intensity among Korean women with rheumatoid arthritis (RA) (n = 246). Data included pain site and intensity, physical function, fatigue, medication attitudes, and learned helplessness (LH) from patient self-report, and Disease Activity Score 28 (DAS28) from chart review. The overall pain intensity was 3.59 out of 10, with a median of 3. The mean number of painful joints was 8.4, with the most commonly reported painful joint groups being the fingers, wrists, and knees. Higher DAS28, impaired physical function, eight or more painful joints, higher levels of fatigue, and higher levels of LH were significantly associated with pain intensity. Our results suggest that pain in women with RA is closely associated with cognitive or psychological variables such as fatigue and LH in addition to inflammation itself. For improved pain management, patients with RA should receive regular counseling to address their feelings of LH and fatigue.