This cross-sectional study examines differentials in age at marriage, collecting data from 665 ever-married women in Howrah district, West Bengal, using a mixed-methods approach across three generational cohorts. Quantitative analyses included ANOVA and multinomial logistic regression, complemented by qualitative interviews to contextualize marriage timing. Results revealed a non-linear trajectory of marriage age across generations. Mean age at marriage was 21.4 years, 23.2 years, and 19.5 years in Generation I, Generation II, and Generation III, respectively, with significant differences. MLR results showed respondents in Generation II had higher odds of marrying at ages 19–24 (RRR = 1.5, CI = 0.6–2.7) and ≥25 years (RRR = 1.4, CI = 0.9–4.0), whereas Generation III women had lower odds at ages 19–24 (RRR = 0.3, CI = 0.2–0.9) and ≥25 years (RRR = 0.6, CI = 0.1–0.9), compared to Generation I. Urban women showed delayed marriage at ages 19–24 (RRR = 3.1, CI = 2.6–11.5) and ≥25 years (RRR = 4.5, CI = 2.2–15.5). Higher educated women increased the likelihood of delaying marriage at ages 19–24 (RRR = 1.6, CI = 0.4–1.9) and ≥25 years (RRR = 1.2, CI = 0.8–1.6). Fathers’ secondary education was associated with marriage at ages 19–24 (RRR = 1.5, CI = 1.0–2.3) and ≥25 years (RRR = 4.6, CI = 1.3–15.8), and fathers’ higher education was associated with marriage at ≥25 years (RRR = 2.6, CI = 1.3–12.8); mothers’ secondary education was associated with marriage at ages 19–24 (RRR = 1.7, CI = 1.0–2.9) and ≥25 years (RRR = 3.1, CI = 1.9–12.3), and mothers’ higher education was associated with marriage at ≥25 years (RRR = 3.2, CI = 1.6–10.4). Respondents in white-collar jobs were more likely to delay marriage at 19–24 (RRR = 1.5, CI = 0.3–2.0) and ≥25 years (RRR = 1.6, CI = 0.8–3.4). White-collar employment of fathers increased the odds of marriage at ages 19–24 (RRR = 1.7, CI = 0.7–2.1) and ≥25 years (RRR = 1.6, CI = 0.4–2.6) and of mothers at ages 19–24 (RRR = 1.2, CI = 0.4–1.6) and ≥25 years (RRR = 1.1, CI = 0.3–1.9). Women from the upper wealth quintile were more likely to marry at ≥25 years (RRR = 1.2, CI = 0.5–2.8). Muslim women showed significantly less likelihood to marry at ≥25 years (RRR = 0.2, CI = 0.1–0.6). Ethnographic narratives revealed tensions between aspirations for daughters’ education and parental anxieties related to employment insecurity, dowry, and premarital relationships, shaping marriage decisions.