In classical Chinese, the distinction between a rhetorical question and a simple question may not be readily clear when interrogative words are used. This paper aims to investigate factors that may determine whether a question formed with an安, yan焉, or heyi何以is a simple question or a rhetorical question; they include the presence of (1) a modal verb; (2) a negative marker in the main clause; (3) condition in the subordinate clause; and (4) a final exclamatory particle. Based on an analysis of these factors, a set of markers is proposed to distinguish a rhetorical question from a simple question and the extent of their reliability is discussed. Furthermore, a scale will be proposed to measure the strength of a rhetorical question based on the set of said markers.