As social creatures, people need to understand others, express themselves, and without doubt, be understood. In this sense, language is seen as an indispensable tool of effective communication. However, the fact that it is considered as a bare-necessity delayed a thorough questioning of Aristotle’s long-embraced presumption that words are the symbols of mental images. It was not until Gottlob Frege in the twentieth-century that the aforementioned issue was analytically studied. Gradually, Frege’s foundational thoughts on the problem of meaning have been shaped by a wide range of views to the date and have eventually turned the matter into a context problem, thus nullifying the opinion that the words are the exact equivalents of thoughts. Thus, subscribing to the view that all semantic elements in the language other than grammar can be evaluated within the scope of context, this paper aims to open the differences and similarities between literary language and ordinary language towards a subjectivity-centred investigation and explores the cognitive processes carried out during meaning-making. Building upon the views of ordinary language philosophers and contemporary theories of pragmatics, the cognitive processes taking place while meaning-making in relation to literary texts are shed light on. Consequently, it is stressed that the ambiguity of meaning/context, despite being an undesirable element in ordinary language where the primary goal is to communicate and to ensure the recognition of emotions and thoughts by the receiver, creates the opportunity to take textual pleasure in the literary language. Finally, the hypothesis that ‘the receiver, who engages in the adventure of constructing their own meaning subjectively to the extent of the ambiguity in the text, receives the same amount of textual pleasure’ is grounded based on Sperber and Wilson’s (1986) relevance theory, with examples especially from poetry.