Expressing condolences is among the least frequently explored expressive speech acts. Just like the other speech acts, it is culture specific, i.e. its realizations vary from culture to culture. This particular paper pioneers the studying of the speech act of expressing condolences in the Macedonian language and culture, and, logically, it draws heavily on the findings and insights gained previously in other cultures, primarily Western (the English speaking countries), but also some more exquisite Eastern ones (Iraqi, Persian, Malaysian, Iranian, etc.). The aim of the study is to make an intercultural comparison and to investigate the presence, or more precisely, the frequency with which the semantic formulas for expressing condolences used in the abovementioned languages and cultures are used in the Macedonian language and culture. In that context, attempts are made to disclose whether Macedonian culture bears a greater similarity to the Western cultures or, perhaps, to the Eastern ones. The research incorporates both a qualitative and quantitative paradigm. The chosen instrument for compiling data is a structured Discourse Completion Task. Bearing in mind the limitations of the DCT, the data from the DCT are compared with the acts of condolences given to one of the author after her father has died in 2016. These data which are not analyzed were identical with the one compiled with the DCT and serves as a confirmation of the validity and reliability of the DCT. Analysis, synthesis and comparison of the results obtained from previous research are the methods utilized for both processing the linguistic corpus and reaching scientifically valid conclusions. The analysis shows that in the Macedonian language and culture, just like in the other languages and cultures, there are primary and secondary semantic formulas for expressing condolences. Some of the primary semantic formulas appear to be typical only of the Macedonian native speakers, whereas some resemble the ones used in Western cultures, and some are closer to the ones used in the Islamic cultures. The study also bears evidence to the fact that in the Macedonian language, the formality of the context and the social status of the interlocutors still influence the choice of the semantic formulas for expressing condolences. Nevertheless, there are also some indications that some of the semantic formulas are undergoing a process of generalization, which practically endorses their usage in both formal and informal domains. Article visualizations: