Understanding the changes in our language abilities along the lifespan is a crucial step for understanding the aging process both in normal and in abnormal circumstances. Besides controlled experimental tasks, it is equally crucial to investigate language in unconstrained conversation. I present an information‐theoretical analysis of a corpus of dyadic conversations investigating how the richness of the vocabulary, the word‐internal structure (inflectional morphology), and the syntax of the utterances evolves as a function of the speaker's age and sex. Although vocabulary diversity increases throughout the lifetime, grammatical diversities follow a different pattern, which also differs between women and men. Women use increasingly diverse syntactic structures at least up to their late fifties, and they do not deteriorate in terms of fluency through their lifespan. However, from age 45 onward, men exhibit a decrease in the diversity of the syntactic structures they use, coupled with an increased number of speech disfluencies.