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Semantics and pragmatics are two complimentary and intertwined aspects of meaning in language. The former is concerned with the literal (context-free) meaning of words and sentences, the latter focuses on the intended meaning, one that is context-dependent. While NLP research has focused in the past mostly on semantics, the goal of this thesis is to develop computational models that leverage this pragmatic knowledge in language that is crucial to performing many NLP tasks correctly. In this proposal, we begin by reviewing the current progress in this thesis, namely, on the tasks of definiteness prediction and adverbial presupposition triggering. Then we discuss the proposed research for the remainder of the thesis which builds on this progress towards the goal of building better and more pragmatically-aware natural language generation and understanding systems.