Shaggy: Can you give us a straight answer?
Mr. E: Where's the fun in that?
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.
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- 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.
- 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.
- 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?