History Main / DelightingInRiddles

* Gollum in ''Literature/TheHobbit'' is a [[DownplayedTrope 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.

* The ''VideoGame/ProfessorLayton'' series runs on this idea--it's a WidgetSeries wherein players are tasked to solve various puzzles while following an in-game story. Each game in the series has relied on [[ExcusePlot increasingly flimsy justifications]] as to ''why'' everyone that Professor Layton and his friends meet is so obsessed with puzzles. It's usually either a SecretTestOfCharacter, a [[PlanetOfHats weird quirk]] of whatever new location the Professor is visiting ("Everyone here loves puzzles!"), or a [[OnlySmartPeopleMayPass test]] to see if Layton and his friends are worthy.

* In Stephen Sondehim's ''Theatre/IntoTheWoods'', this is the defining trait of the Mysterious Man, an enigmatic figure who dwells in the titular forest. His [[RhymesOnADime rhyming]] CatchPhrase 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, SurprisinglyRealisticOutcome occurs and people either ignore him or [[BigShutUp tell him to shut up]]. The tendency is [[DeconstructedTrope deconstructed]], though, when the Mysterious Man is revealed to be the Baker's DisappearedDad--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.''

There are many reasons why characters may puzzle others by [[CrypticConversation speaking in riddles]]. Sometimes [[FigureItOutYourself it may be a test for the protagonist to figure out the meaning]]. Or [[SpySpeak 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 [[MadOracle 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, {{Koan}}s may serve both as a way of amusement for the mentor and as a challenge for the disciple. [[EccentricMentor Eccentric Mentors]] and [[TricksterMentor Trickster Mentors]] are especially prone to this; beautiful females and [[LoveInterest Love Interests]] can also have such inclinations, since mysteries and riddles are often [[TricksterGirlfriend the best way to intrigue the hero]]. As a result, [[TeacherStudentRomance a love interest who doubles as a mentor]] would almost inevitably indulge in this.

Compare TeasingFromBehindTheLanguageBarrier, when a foreign language is used for the same purpose, and LovesSecrecy, when a character delights in keeping secrets from others. Subtrope of ItAmusedMe; may overlap with ProverbialWisdom.

* This is actually the calling card of Edward Nygma aka Comicbook/TheRiddler from [[Franchise/TheDCU DC comics]]. In ''{{Series/Gotham}}'', where he starts off as a forensic expert in police, he often annoys his colleagues by presenting his information in riddles.

* In ''Fanfic/ChildOfTheStorm'', Doctor Strange delights in being cryptic - since he's an enormously powerful {{Seer}} and [[TimeMaster Chronomancer]], with a reputation for never lying and deep eccentricity, he gives TheFairFolk a run for their money at mastery of ExactWords.

* In ''Fanfic/TheVow'', Ah-Ma [[WesternAnimation/KungFuPanda2 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.

* In Stephen Sondehim's ''Theatre/IntoTheWoods'', this is the defining trait of the Mysterious Man, an enigmatic figure who dwells in the titular forest. His [[RhymesOnADime rhyming]] CatchPhrase 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, RealityEnsues and people either ignore him or [[BigShutUp tell him to shut up]]. The tendency is [[DeconstructedTrope deconstructed]], though, when the Mysterious Man is revealed to be the Baker's DisappearedDad--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.''

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

* In ''Fanfic/ChildOfTheStorm'', Doctor Strange delights in being cryptic - since he's an enormously powerful {{Seer}} and [[TimeMaster Chronomancer]], with a reputation for never lying (even suggesting that he will is his personal BerserkButton, [[EveryoneHasStandards since he's lost almost everything else]]), and deep eccentricity, he gives TheFairFolk a run for their money.

* ''Literature/TheKingKillerChronicles'' has Kvothe's EccentricMentor and BunnyEarsLawyer 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.

'''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, {{Koan}}s may serve both as a way of amusement for the mentor and as a challenge for the disciple. [[EccentricMentor Eccentric Mentors]] and [[TricksterMentor Trickster Mentors]] are especially prone to this; beautiful females and [[LoveInterest Love Interests]] can also have such inclinations, since mysteries and riddles are often [[TricksterGirlfriend the best way to intrigue the hero]]. As a result, [[MentorShip a love interest who doubles as a mentor]] would almost inevitably indulge in this.

[[folder:Visual Novels]]
* In ''{{VisualNovel/Xblaze}}'' Lost Memories, the MysteriousWaif "Nobody" who lived in the Phantom Field liked to entertain herself with riddles. When our hero "Watashi" stumbled into the realm, Nobody gave her riddles regarding the "memory fragments" they found in the realm.

[[folder:Western Animation]]
* Mr. E from ''WesternAnimation/ScoobyDooMysteryIncorporated'' 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?

* In ''Fanfic/ChildOfTheStorm'', Doctor Strange delights in being cryptic - since he's an enormously powerful {{Seer}} and [[TimeMaster Chronomancer]], with a reputation for never lying (it's implied that he's bound not to) and deep eccentricity, he gives TheFairFolk a run for their money.