Background: Mammography screening uptake in Singapore remains below 40% despite campaigns and subsidies. Natural language processing (NLP) can extract nuanced attitudes from free text that fixed response options miss, revealing latent factors influencing breast cancer (BC) screening behavior. Objective: This study characterized women’s attitudes toward mammography using mixed methods data, examined associations between BC awareness and screening willingness, and identified barriers and facilitators through NLP of free-text responses. Methods: We conducted a cross-sectional study within the multicenter cohort in Singapore (October 2021-December 2023). In total, 4169 women aged 35‐59 years (median 48, IQR 43‐54) were recruited via convenience sampling (3 hospitals and 2 polyclinics). Participants completed online structured questionnaires on demographics and screening history, then a BC education quiz with feedback. Participants answering >80% correctly were classified as “BC-aware.” Posteducation, participants reported screening willingness (motivated or neutral) with optional free-text explanations. Logistic regression models (adjusted for study site, age, ethnicity, marital status, housing, and education) examined the associations with willingness. For 3819 English-language respondents, biterm topic modeling identified themes and sentiment analysis quantified emotional tone. Statistical significance: =.05. Results: Overall, 79% (3287/4169) were BC-aware, and 94% (3908/4169) reported increased motivation posteducation. BC-aware women had higher screening motivation than BC-unaware women (adjusted odds ratio [aOR] 2.88, 95% CI 2.19‐3.80;