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Using the 1958 British National Child Development Study, I construct a language-based index of gender atypicality from 10,507 age-11 essays imagining life at 25 and link it to adult trajectories. After masking explicit gender cues with a constrained large language model, essays are embedded with a transformer and used to train a sex classifier; the calibrated probability of the non-true sex defines a continuous atypicality score. Adjusted regression models show that higher atypicality predicts greater likelihood of managerial/technical class at ages 33 and 50, slightly poorer midlife health and wellbeing, lower odds of ever marrying, and higher odds of ever having a same-sex partner, with modest, sex-differentiated effect sizes.