The subject of research is the novel “Headlong” by Michael Fraine, published in 1999. The purpose of the study is to study the concepts of authenticity and meaning in art, presented by the author through an analysis of expressive means and stylistic techniques in this novel. The methods used to obtain results include a formal method, a hermeneutic method, psychological and existential methods, and an applied method, since the study was conducted during the teaching of an extensive reading course for students of the 4th year of the Foreign language: two foreign languages specialty. Michael Fraine's “Headlong” offers a thought-provoking exploration of authenticity and meaning not only in art, but also in real life of both the fiction character and the reader. Through the protagonist's quest for a lost painting, the novel challenges conventional notions of authenticity, emphasizing the subjective nature of perception and interpretation. Frayn underscores the role of context in shaping the meaning of art and highlights the complex interplay between art and society. Ultimately, “Headlong” invites readers to reflect on the intricate relationship between authenticity, meaning, and the ever-evolving nature of art. This essay explores how Frayn's skillful use of language, narrative structure, and character development enhances the exploration of authenticity and meaning in art, shedding light on the complex interplay between perception, interpretation, and the subjective nature of artistic value. The obtained results are of applied character, since they can be used for inclusion in educational syllabi in the English language and Literature of Great Britain, or used to illustrate events in art circles or courses and/or to organize extracurricular events, such as debates about the role of art or about the boundaries between reality and perception.