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Despite considerable health risks due to lower levels of estrogen production and the compounding antiestrogenic effects of nicotine, postmenopausal females continue to smoke. These females face significant barriers to cessation, including negative affect, weight concerns, and menopausal symptom severity. The current pilot study explored the effect of negative affect, weight concerns, and menopausal symptom severity on motivation and readiness to quit smoking. Eighteen postmenopausal smokers were randomized to receive brief motivational interviewing (B-MI; n = 8) or control treatment (i.e., a 1-hour video, n = 10). Participants completed measures of negative affect, weight concerns, and menopausal symptoms, as well as measures of motivation and readiness to quit. Motivation and readiness to quit were reassessed one week following treatment. At baseline, weight concerns, specifically surrounding smoking to prevent overeating, were identified as related to increased motivation to quit smoking. Menopausal symptom severity, specifically somatic symptoms, assessed at baseline, was associated with increased readiness for cessation. B-MI did not increase motivation or readiness to quit; however, results indicate that cigarettes per day decreased from baseline to follow-up by approximately 20–30%. These results provide valuable insight into enhancing engagement in a cessation treatment among this population.