There are many reasons why characters may puzzle others by speaking in riddles. Sometimes it may be a test for the protagonist to figure out the meaning. Or they have to employ a code to keep the meaning hidden from strangers. In other cases, they simply cannot express their thoughts properly due to being mentally unhinged... And finally, there is the simplest reason: they may be doing it for fun, as an unusual form of amusement.
Very many mentors, sages and oracles can be suspected of this due to their cryptic speech mannerisms, though they would rarely admit to it. This motive often overlaps with the others listed above: for example, Koans may serve both as a way of amusement for the mentor and as a challenge for the disciple. Eccentric Mentors and Trickster Mentors are especially prone to this; beautiful females and Love Interests can also have such inclinations, since mysteries and riddles are often the best way to intrigue the hero. As a result, a love interest who doubles as a mentor would almost inevitably indulge in this.
Compare Teasing from Behind the Language Barrier, when a foreign language is used for the same purpose, and Loves Secrecy, when a character delights in keeping secrets from others. Subtrope of It Amused Me; may overlap with Proverbial Wisdom.
- In Child of the Storm, Doctor Strange delights in being cryptic - since he's an enormously powerful Seer and Chronomancer, with a reputation for never lying (even suggesting that he will is his personal Berserk Button, since he's lost almost everything else), and deep eccentricity, he gives The Fair Folk a run for their money.
- In The Little Prince, a Harry Potter/The Chronicles of Narnia crossover fanfic, the eccentric magician Coriakin is depicted as the mentor of young Dumbledore and Grindewald. He delighted in giving them advice in cryptic Koan-like form.
- In The Vow, Ah-Ma the Soothsayer is a wise old lady and a seer who just loves giving advice in vague riddles and ripping off his old foster child Shen's silk clothes to irritate him.
- As per canon, Yoda from Star Wars: Lineage is an Eccentric Mentor who seldom, if ever, gives a straight answer to anything.
- Tia Dalma from Pirates of the Caribbean. It is often implied that her cryptic speech patterns are due to the fact that she takes joy in allowing people to figure things out by themselves.
- Nightfall (Series): Prince Vladimir puts Myra through a series of tests to determine is she is useful to him alive. She must answer his riddles without knowing what he is looking for and what is a part of the test.
- Emmie Reese, the main character's wife from The Harry Reese Mysteries series by Robert Bruce Stewart. She simply loves all sorts of pranks, surprises and schemes, and keeps many secrets from her husband. She will only speak clearly when she absolutely has to; otherwise she almost always speaks in riddles.
- The beautiful Naina from Boris Akunin's Pelagia And The White Bulldog often talks like this, mainly for the purpose of intriguing everyone around her (especially the opposite sex):
She read somewhere that modern young ladies always speak in riddles, and she's practising on us.
- Gollum in The Hobbit is a downplayed example: he doesn't speak in riddles all the time, but he's more than happy to challenge Bilbo into a game of riddles.
- According to the same book, dragons in general, including Smaug, enjoy being spoken to in riddles.
- Angela the Herbalist from Inheritance Cycle frequently speaks in Non Sequiturs and cryptic statements, and the others' astonished reactions seem to amuse her.
- In Robin Jarvis' Deptford Mice books, the bat brothers Orfeo and Eldritch will give predictions, but in such a cryptic manner that no one can make any sense of what they say. They get enjoyment from confusing those who come to them for help.
- The King Killer Chronicles has Kvothe's Eccentric Mentor and Bunny-Ears Lawyer Master Elodin, who devises lessons for his student like standing out in a storm, naked, or ripping up a pillow, chasing the fluff throughout the room, and cursing up a storm in several different languages when he bangs his knee, then limping out of the room.
Elodin: Uresh. Your next assignment is to have sex. If you don't know how to do this, see me after class.
- In Stephen Sondehim's Into the Woods, this is the defining trait of the Mysterious Man, an enigmatic figure who dwells in the titular forest. His rhyming Catch Phrase is "When first I appear, I seem mysterious—but when explained, I'm nothing serious," which is itself a riddle—a riddle with the answer "a riddle." He absolutely delights in the confusion and frustration of those who hear his cryptic clues, although by the end of the first act, Reality Ensues and people either ignore him or tell him to shut up. The tendency is deconstructed, though, when the Mysterious Man is revealed to be the Baker's Disappeared Dad—he was too proud and ashamed to admit his mistakes and fled to the woods after his wife died in childbirth with the Baker's sister Rapunzel, and uses riddling to keep himself from having to confront the reality of his own past. In "No More," the Baker, who is planning to flee his responsibilities in a similar way, begs the Mysterious Man to stop his constant puzzles—and he complies with a straightforward answer about how running away absolutely destroyed his life and has left him feeling empty and hopeless for decades.
- The Myst series is full of this trope; most of the puzzles that the player must solve are given the in-story justification of their creators loving riddles and using them to challenge those who would try to learn their secrets.
- The Professor Layton series runs on this idea—it's a Widget Series wherein players are tasked to solve various puzzles while following an in-game story. Each game in the series has relied on increasingly flimsy justifications as to why everyone that Professor Layton and his friends meet is so obsessed with puzzles. It's usually either a Secret Test of Character, a weird quirk of whatever new location the Professor is visiting ("Everyone here loves puzzles!"), or a test to see if Layton and his friends are worthy.
- Mr. E from Scooby-Doo! Mystery Incorporated is this one. He hangs a lampshade in one episode when he wants to give a Riddle to Mystery Inc, but Shaggy demands a straight answer.
Mr. E: Where's the fun in that?