The study analyzes the linguistic and stylistic features of comic texts in terms of their influence on translation peculiarities of short situational utterances. The relevance of this work is preconditioned by the fact that the issue of adequate translation and understanding of humor in English is becoming more and more relevant over time due to widespread prevalence of real interaction in the transcultural space. Short humorous texts can be found in different conversational situations, but most often in situations of real communication, which, in turn, allow establishing contact and maintaining productive relationships with representatives of other linguocultures. With the reference to complex methodology, the authors analyze short humorous utterances in the virtual discourse of English messengers. Based on the analysis of a vast representative material, the authors conclude that it is necessary to take into account not only the norms and rules of the literary language, but also the non-literary features of the language (for example, “the mobile language of youth”). It means the need to translate combinations of slang and graphic signs with their specific meaning in short humorous texts. It also entails the implementation of an adequate perlocutionary effect. The peculiarity of short humorous texts translation is largely related to the phenomenon of written pronunciation, as well as imitation of the oral register of communication. The authors’ conclusions prove that in order to comply with different variants of explication of these contaminated characteristics in the target text, the use of modulation transformations, differentiation and functional replacement, as well as compensation and zero translation - complex lexical transformations, is required. Another criterion influencing the translation peculiarity of these humorous texts is the optional and obligatory explication of the comic element. The contextual analysis of the texts confirmed that in more than 30% of cases, the author generated the comic component of the text unintentionally. When conveying random humor, it is important to preserve the situation of the original and the style of speech of the author of the original message, which entails the emulation of speech features used in the framework of self-presentation strategy.