The word "guess" in literature has been employed in remarkably diverse ways, evolving from casual interjections of uncertainty to devices that invite readers into a shared act of conjecture. In some works, such as Sinclair Lewis's Babbitt ([1], [2], [3], [4]), "guess" punctuates conversational asides, blending casual speech with irony or resignation. In other texts it functions as both a prompt and an expression of speculative thought, as seen in Cleland’s Memoirs of Fanny Hill ([5]) and Dickens's Our Mutual Friend ([6], [7]), where it both challenges and entertains the audience by leaving room for interpretation. Furthermore, in the treatments by authors like Dostoyevsky ([8], [9], [10], [11]) and Dumas ([12], [13], [14], [15], [16]), "guess" often signals a deeper psychological or moral uncertainty, encouraging readers to consider hidden motivations or unresolved dilemmas. Even when "guess" appears in more playful or ironic contexts—as in Twain’s sparse “Well, guess” ([17]) or Carroll’s wonderment in Alice's Adventures in Wonderland ([18])—it underscores the dynamic interplay between stated fact and the reader’s expectation, demonstrating a flexibility that has made "guess" a subtle yet powerful tool in literary dialogue.