The object of this paper are two types of pronominal possessive constructions in Serbian language, out of which one is expressed using possessive adjectival pronoun, while the other is expressed using personal pronoun in dative (Moja drugarica je diplomirala / Drugarica mi je diplomirala). The aim of the paper was to determine the contextual influences on the speaker’s preference for one of these two constructions. Our hypothesis was that the thematization of the possessor represents one of the factors, considering the same form of dative logical subject, and that social distance / proximity represents the other factor, considering the same form of the ethical dative. A preliminary quantitative research was conducted, with Likert scale acceptability judgements, as well as a qualitative research, with a focus-group interview. The results of the quantitative questionnaire didn’t confirm the hypothesis, given that the possessive adjectival pronoun had higher rates in all of the conditions, although the rates of dative constructions were notably lower in the conditions without thematization of the possessor. The results of the focus-group interview, on the other hand, showed the speakers’ intuitions of the influence of thematization of the possessor, as well as social closeness of the possessor (when thematized) and the possessed. In addition, the interviewees mentioned the social closeness of the speaker and the listener as one of the factors, which could represent one of the reasons for the lack of the influence of forementioned factors in the quantitative section of the research. Further implications of this research apply to the interconnectedness of the case meanings, which led to the expressiveness of the dative structure, as well as to the influence of information structure on the additional meanings that can be conveyed by choosing dative possessive construction.