Extensive cross-linguistic data document a wide gamut of semantic and pragmatic uses of the diminutive that revolve around the fundamental concepts of `small' and `child'. As typical inventory of informal registers, diminutives are utilized as pragmatic markers of politeness in a wide range of contextual meanings. This dissertation is intended to fill some major gaps in the systematic and empirical research on the formation and pragmatic uses of the diminutives in Macedonian and to explore the role of diminutivization in a broader linguistic framework, by examining the consistency of the field of diminutives, the core and peripheral meanings of the diminutive, their typology, as well as their pragmatic potential. The morphology and pragmatics of the diminutive is examined by combining data from electronic and printed sources, video recordings of natural conversations, as well as from material collected from participant and non-participant observations. At the level of morphology, it is argued that three fundamental semantic constraints underlie the formation of diminutives: [-big], [+ emotional], and [+ informal]. Furthermore, it is shown how diminutive combinability is rule governed in Macedonian by proposing sets of formal constraints for all grades of diminutives. At the level of pragmatics, the pragmatic functions of the diminutives proper and the related periphrastic diminutive malku are investigated in a variety of contexts involving child-directed speech (CDS) and adult communication. By analyzing the pragmatic functions of the diminutive in a series of speech acts, and drawing upon cross-cultural interpretations suggested by Wierzbicka (1991), it is argued that, in Macedonian, social bonding, cordiality, intimacy or affection are pragmatically more salient than personal autonomy in the Anglo-Saxon societies, realized through non-imposition, tentativeness, or similar pragmatic strategies for saving face. Additionally, it is contended that there exist cultural differences in the assessment of the concept of imposition between these societies. The analyses of the pragmatic potential of the diminutive proper and the periphrastic diminutive 'malku' give rise to the claim that Macedonian culture is predominantly founded on the pragmatic principle of positive politeness.