This article probes the connections between the metaphysics of meaning and the investigation of human communication. It first argues that contemporary philosophy of mind has inherited most of its metaphysical questions from Brentano’s puzzling definition of intentionality. Then it examines how intentionality came to occupy the forefront of pragmatics in three steps. (1) By investigating speech acts, Austin and ordinary language philosophers pioneered the study of intentional actions performed by uttering sentences of natural languages. (2) Based on his novel concept of speaker’s meaning and his inferential view of human communication as a cooperative and rational activity, Grice developed a three-tiered model of the meaning of utterances: (i) the linguistic meaning of the uttered sentence; (ii) the explicit truth-conditional content of the utterance; (iii) the implicit content conveyed by the utterance. (3) Finally, the new emerging truth-conditional trend in pragmatics urges that not only the implicit content conveyed by an utterance but its explicit content as well depends on the speaker’s communicative intention.