This chapter, devoted to the study of words, meaning, and semantics, is composed of three parts. “The study of word meaning is crucial to the inquiry into the fundamental properties of human language”, declares Stanford Encyclopedia of Philosophy (SEP, henceforth). Given the primacy of language, this also applies for human cognition. In this chapter, we first trace human thought about language, its components, and its relationship to species and reality from the perspectives of philosophy, logic and the physiological cognitive apparatus. Next, we present how in practice, that understanding has shaped the practice of NLP. Discourse between an author and three generative artificial intelligence (AI) applications—ChatGPT, Anthropic’s Claude, and Google Gemini—is offered and compared. We identify where natural language processing (NLP) is deficient given known gaps, and we prescribe a plausible solution.