This dissertation has two central foci: (i) it examines the behavioral contrasts of perspective-sensitive elements such as evidentials in questions and assertions; (ii) it investigates the connection between alternative questions and the clausal disjunction-embedder 'whether'. The overall theme of the dissertation is an exploration into the interaction of questions and doxastic domains, set within formal syntactic, semantic and pragmatic theories. The main empirical focus is the South Asian (Indo Aryan; India, Bangladesh) language Bangla (also known as Bengali), which is analyzed based on the native speaker judgements of the author, as well as several surveys collected from other native speakers. The interaction of perspectival elements with speech acts have been a relatively under-explored area of study. I undertake the study of evidentials (elements marking an agent's source of information). I argue for a theory that is both syntax and semantics informed. In particular, I propose that evidentials crucially take only finite clauses as complements, and derive their interpretation from a `judge' that is syntactically represented in the left periphery, and that interacts with other perspectival heads both inside the finite clause as well as the speech-act projection. This approach enables a unified analysis of the Bangla evidential 'naki', that changes its evidential flavor based on its syntactic position. In the interpretative component, I argue that evidentials embody either Involved (committed) or Uninvolved (not committed) sources of information. I propose that the world's evidentials come in two shapes: those that effect Interrogative Flip (shifting of perspective from the speaker to addressee in questions) and those that do not, and I locate the difference in a formal semantic property. This formal property predicts the presence or absence of bias in questions with evidentials, and forges a cross-linguistic link between evidentiality and bias. The second focus of the dissertation is alternative questions and disjunction. The main claim offered is that there is a crucial connection between interrogative and 'whether' in Bangla: they are underlying the same element 'kina'. The surface differences between the two constructions is shown to be derivable from the syntactic processes of head movement and ellipsis. This unification claim has not been undertaken for any other language in the literature. I argue that this claim is also semantically viable, and propose an Alternative Semantics-theoretic analysis that can explain the presence of 'kina' (`whether') in Bangla alternative questions. This analysis, while focussed on Bangla, also makes predictions in an area that is understudied in the world's languages - the interrogative-boolean divide within the universal disjunction space. I undertake a comparative study with Mandarin Chinese, and investigate the locus of the divide in the two languages. This study fits into the overall theme of the dissertation by furthering the understanding of Bangla questions and their interaction with other domains such as disjunction and perspective-sensitivity, as viewed from the standpoint of the syntax-semantics-pragmatic interfaces.