This paper is an attempt for a comparative study of two famous short stories, one by Anton Chekhov called “The Kiss” and the other by Thomas Wolfe by the name of “The Far and the Near”. The focus of the study is on the analysis of the theme of illusion versus reality, and the approach to the stories has basically been analogical in essence which compares and contrasts this theme in the two stories, and the relevant aspects of the stories such as characterization, symbols, or motifs, to name but few, have been deployed as technical/literary tools for the better apprehension of the working appearance and reality on the protagonists. The results of the study show that the characters’ inability in recognizing the true meaning of what appears to them as reality on the one hand, and their idealization of the apparent reality caused by their subconscious desire for self-deception on the other, have dismantled the protagonists’ power of perception; the ensuing disillusionment caused by the final affirmation of reality which is achieved by recognition of reality/truth leads to their catastrophic end, that is, a deeper alienation and sharper feeling of alienation and desperation. The study finds significance in the fact that no similar comparative study of the two short stories have been yet done. The authors hope that this study will contribute hugely to the criticism of the two short stories and start a resurgence of interest in the study of them comparatively utilizing different approaches.