This thesis deals with the phenomenon of meaning in thought and language, and its relation to the phenomenon of rule-following. It starts from Wittgenstein’s departure from the traditional conception of meaning and his new understanding of its origin. Wittgenstein rejects the idea that mental states play a decisive role in establishing and understanding of meanings. Instead, he emphasizes the importance of language use and of analyzing different contexts —different “language games”—in which words acquire their meanings. Offering an original interpretation of the relevant parts of Wittgenstein’s Philosophical Investigations, Saul Kripke has set up a well-known skeptical argument whose radical conclusion is that meanings do not exist. This argument will be presented in the third part of the paper. In the fourth part, the conditions that a theory of meaning must satisfy in order to avoid Kripke’s skepticism will be explicated. One such theory was proposed by Paul Horwich under the label “Use Theory of Meaning” (UTM). This theory will be presented in the fifth part of the thesis. The sixth, final part considers the idea that current artificial intelligence systems known as Large Language Models (LLM) or chatbots operate with meanings, provided that meanings of words can be reduced to their use by application of context-sensitive rules.