This paper analyzes the utilization of exclamation mark as a means of expressing a variety of emotions in two books written in the 19th c. by the Bulgarian monk Neophyte of Rila: The First Bulgarian Grammar (1835) and the Description of Rila Monastery (1879). The section of the grammar that addresses punctuation, particularly the exclamation mark, is examined by comparing it to other grammars that were published during the same period. Additionally, the sentences that contain exclamation mark have been selected from the Grammar and the Description. Some of them are presented here in conjunction with brief remarks that elucidate the intended emotional impact and the sentiments they embody. A comparative analysis of the two books reveals a subtle difference. In the Grammar, the author utilizes the exclamation mark predominantly to convey negative emotions. In the Description, although the negative tone predominates in the exclamatory sentences, there are also some that are rather positive. The broader range of emotions articulated in the Description is presumably attributable to its vivid and expressive nature, which starkly contrasts with the technical tone of a grammar book.