Understand the rules of riddles. Most riddles deal with very familiar topics. Their difficulty comes in how those topics are described. Riddles often create a pattern of associations in order to direct you to the answer. For example, a popular riddle from J.R.R. Tolkien’s The Hobbit goes: “Thirty white horses on a red hill, / First they champ, / Then they stamp, / Then they stand still.” This riddle uses familiar ideas (horses, hills) to figuratively express the answer (in this case, “teeth.”)