->'''The Fairy Godmother:''' Ah, but this is no ordinary ScienceFair! The winner will marry the prince!\\
'''Cinderella:''' Are they insane? Marriage amongst royalty involves any number of political and trade factors that directly impact their countries' place within the geopolitical framework!\\
'''The Fairy Godmother:''' It gets worse. Both princes are inordinately fond of miniature volcanoes.
-->-- ''Webcomic/GirlGenius, [[ShowWithinAShow Cinderella Parody]]''

"You want to marry [[EverythingsBetterWithPrincesses my daughter]]? Prove yourself worthy; kill yonder dragon," the King proclaims, and the heroes gather to win the fair damsel's hand - a FairyTale scenario still used today.

Historically, used straight, as a way to get the story going.

The reason for challenge varies.
* The king invented it to test the suitors for the [[LivingMacGuffin princess's]] hand. This is often a GenderFlip, but the test for a bride is very different: of domestic skills.
* The king uses it to [[StandardHeroReward lure heroes]] to help the kingdom, which is sometimes a GenderFlip.
* It features as a way to have the [[DistressedDude prince]] or [[DamselInDistress princess]] rescued; this is more often a GenderFlip, but the precise challenges tend to differ according whether it is a hero or a heroine challenged, as the princess is more often ChainedToARock and the prince deathly ill and in need of [[HealingHands magical healing]].
* The king does not want to see her married off and resorts to this as a form of ParentalMarriageVeto. The challenge is either [[ImpossibleTask impossible]] or [[TheUriahGambit deadly]]. It may be targeted at a particular suitor that the king needs to get rid of, or maybe the kingdom is infested with a surplus of DumbJock types.
* It's a SecretTestOfCharacter. For example, perhaps the king wants a very particular type of man to marry his daughter, and the man who tries to murder the (perfectly nice, intelligent, reasonable) dragon will fail, while the one who offers it some of his lunch will pass.

Sometimes the princess (or prince) lay down the challenge themselves. This tends to get treated with less sympathy.

If [[RoyalBrat the king]] decides after all that fulfilling the challenge doesn't make you worthy (frequently if he didn't realize it would be RagsToRoyalty), DudeWheresMyRespect or MovingTheGoalposts may ensue; the opening EngagementChallenge was open to all comers, but the subsequent ones only to the peasant who succeeded -- and quite frequently an ImpossibleTask . Occasionally, the king makes this promise in order to rid himself of someone, sending him to do something he doesn't want done but which, he thinks, will kill him. Or [[XanatosGambit something he]] ''[[XanatosGambit does]]'' [[XanatosGambit want done but will probably kill him]].

Another problem is often a [[FakeUltimateHero false hero]], who claims to have done the deed. Many false heroes have cut off the heads of the monster only to discover that the hero had already cut out their tongues. The heroine may be threatened to silence but [[SingleWomanSeeksGoodMan will tell the truth if the hero is there to protect her]].

These days there are usually complications. Sometimes, the EvilChancellor set up the challenge, tricking the king into getting some naive hero to collect his [[MacGuffin MacGuffins]] or killing his enemies. Sometimes the hero befriends the poor misunderstood dragon, but still gets the girl. Having a dragon at your side is an amazingly effective negotiating tool. Sometimes the hero completes the challenge without realizing there's a reward; a case of AccidentalMarriage which can lead to some seriously miffed princesses. Of course, if the hero does want the marriage, the [[RebelliousPrincess more rebellious princesses]] will often be highly scornful of the idea of marrying someone just because they can kill an overgrown lizard.

With the cleverer heroes and NoManOfWomanBorn level conditions, ProphecyTwist-style wrangling may occur.

The FracturedFairyTale often plays with this. The ScheherezadeGambit enters into some variants where it is a test of wits rather than a test of courage.
----
!!Examples

[[foldercontrol]]

[[folder: Anime And Manga ]]
* In ''KenichiTheMightiestDisciple'', [[BadassGrandpa Elder]] tells Kenichi that he would only allow him to propose to [[ActionGirlfriend Miu]] (Elder's granddaughter) if Kenichi beats him in a fight. Elder is known as "the man without enemies". It's even better in Japanese: "man without enemies" is the literal definition of the word "invincible".
* In ''KimagureOrangeRoad'', a flashback reveals that Kyosuke's grandfather set up something like this for his father. The challenge was to bring snow down from the top of a mountain. As a normal human, Kyosuke's father was unable to complete the challenge... without help from the Esper he was seeking to marry.
* In ''HoneyHoneyNoSutekiNaBouken'', the princess ''herself'' sets up the quest. She has rich suitors from around the world after her fabulous fortune, and frustrated at her options, she sticks her enormous diamond ring into a cooked fish and throws it outside. The main character's cat eats the fish, swallowing the ring, and runs off. The princess says whoever can retrieve the ring will marry her, setting off the events of the series, which is a wacky chase across Europe for a poor young waitress and her cat.
* In ''TokyoMewMew'', Ichigo's father challenges Aoyama to a kendo duel in order to let him continue seeing her. After Ichigo learns that he had been subjected to a similar challenge to continue seeing her mother, she, [[GenerationXerox like her mother before her]], runs in and offers to continue the duel on Aoyama's behalf, convincing her father to accept him.
* Subverted in ''Manga/{{Bakuman}}''. After Akito Takagi, while meeting with his girlfriend Kaya Miyoshi's parents, mentions the name of his partner Moritaka Mashiro, Kaya's father challenges him to a sparring match to test his determination, but it turns out that it was a ruse to get the two of them away from his wife and daughter to talk about the relationship between Mashiro's uncle and Miho Azuki's mother.
* In ''LightNovel/HighSchoolDXD'', Issei crashes Rias and Raiser's marriage to take Rias back. Sirzechs then appears and tells him that if he wants his sister, he'll have to defeat Raiser. Naturally, Issei complies. [[CrazyPrepared And he brought some stuff with him too.]]
* In ''Manga/{{Beelzebub}}'', Aoi's grandfather refuses to let her date anyone he doesn't consider worthy--generally, by [[OldMaster fighting them and evaluating their skills]]. Oga is the only one he has ever acknowledged. Later, during the school trip, Oga wins a fight with the right to date Aoi as the prize. Oga [[ObliviousToLove seems completely unaware of the consequences of either of these events]], and Aoi is [[CannotSpitItOut too embarrassed to explain it]].
* Similarly to the RealLife example, Chi-Chi does this to Goku in ''DragonBall'' after the two had grown up - granted, the contest was instead "Beat me and I'll tell you my name", but the engagement followed right on the heels of it.
** Mr. Satan also freaks out when he realizes that Videl is in love with someone, saying that any boy who wants to date her would have to be capable of defeating him in combat (he's a long-running Martial Arts World Champion). Hilariously enough, Videl's boyfriend happens to be Gohan, who is one of the only teenage guys on the planet who could ''easily'' defeat Mr. Satan.
* In ''LightNovel/TheCircumstancesLeadingToWaltrautesMarriage'', the Valkyrie Waltraute says she will only marry Jack if he can climb Yggdrasil all the way up to Asgard. She wasn't expecting him to actually try it, but he does. In a subversion, he ends up falling off halfway, but she catches him and declares him the winner because his determination moved her. They marry.
* An unusual version occurs in volumes 4-5 of ''DanceInTheVampireBund''. The only three vampires of sufficient rank to be a socially acceptable match for Mina decide that they're tired of waiting for her to decide which of them she's going to marry (Despite being prepubescent and thus being ineligible for marriage to ''anyone'' at this time) and so they come up with and execute an EngagementChallenge ''without her knowledge or consent''. Made worse by the fact that the challenge in question is to see which of them (Or rather, whose champion) is able to murder her closest friend. Fortunately, Akira kills two of them and subdues the third, winning Mina the right to order them back to their estates until she's ready to decide who she wishes to marry.
[[/folder]]

[[folder:Ballads]]
* The ballad "Scarborough Fair" is about a scorned man offering his former lover a series of impossible challenges to complete before he'll take her back (like weaving a seamless shirt in a sycamore wood lane, gathering it in a basket made of flowers, and washing it in a dry well).
** An older version of the song has the initial impossible request come from the guy, and everything else is the girl's response- demanding him plough land between "salt water and sea strand", reap the crop with a ''leather'' sickle, etc. So, it's either a "Hell no, take that" response, or a Beatrice and Benedick situation...
** The oldest version (Literature/{{Child Ballad|s}} #2) has an [[TheFairFolk elf]] or a DirtyOldMan demanding the woman become his lover ''unless'' she can make the shirt, and she escapes the implied rape by demanding impossible tasks of him in return.
* In Literature/{{Child Ballad|s}} #47 "[[http://www.sacred-texts.com/neu/eng/child/ch047.htm Proud Lady Margaret]]", the title character sets riddles and executes those who do not answer. A knight comes and answers them; then he explains he is her brother, come to humble her pride. She says she will go with him anyway, and he reveals that he is already dead.
[[/folder]]

[[folder:Comics]]
* ''{{Erstwhile}}'' poses one to [[GuileHero a young girl]] in "The Farmer's Clever Daughter".
-->'''King:''' Since you think yourself so clever, I want to give you a riddle to solve. If you solve it, not only will I return your father to his land...but I will also marry you.
[[/folder]]

[[folder: Fairy Tales ]]
* Jewish folktale. Everyone had to do some task and if they succeeded they could marry the princess and if they failed, they would be beheaded. So, when the hero succeeds after his brothers have failed, the first thing he does is behead the princess and send her head in the mail back to her father.
* The man who discovered what happened to [[Creator/TheBrothersGrimm the Grimms']] "Literature/TheTwelveDancingPrincesses" was entitled to marry one of them.
* "Literature/JesperWhoHerdedTheHares" brings the pearls the king demanded. The king doesn't approve of Jesper and starts piling up the tasks.
* "Literature/KateCrackernuts" demands to marry the ill prince before she stays by his bed for a third night.
* "Literature/MollyWhuppie" having two older sisters, and the king three sons, she carries out three challenges, marrying off each pair.
* The "Literature/ThePrincessOnTheGlassHill" could be won only by a man who climbed the hill.
* In "[[http://www.surlalunefairytales.com/pentamerone/11sisters1911.html The Three Sisters]]", the king pledges that any woman who cures his son may marry him; his secret wife cures him. (The prince refuses to marry because he's already married, but the princess reveals herself.)
* In "[[http://www.surlalunefairytales.com/pentamerone/14serpent1911.html The Serpent]]", a [[TalkingAnimal snake]] wants to marry a princess; her father demands three {{Impossible Task}}s, but the snake succeeds, and the king reluctantly gives him the princess's hand. The snake is revealed to actually be a [[BalefulPolymorph prince under a curse]], but when the King [[MyGodWhatHaveYouDone burns his shed snakeskin]], he is transformed into a dove and forced to flee the kingdom. The king pledges that any woman who cures his son may marry him; the princess reaches the kingdom and cures him.
* The king promised the kingdom and his daughter's hand in marriage to whoever watched over his "[[http://www.surlalunefairytales.com/authors/asbjornsenmoe/sevenfoals.html Seven Foals]]" all day.
* In [[Creator/TheBrothersGrimm Grimms']] "[[http://www.surlalunefairytales.com/authors/grimms/60twobrothers.html The Two Brothers]]", the king has promised his daughter to anyone who rescues her from the dragon; after the huntsman kills the dragon, [[FakeUltimateHero the marshall]] cuts his head off while he sleeps, but his {{Talking Animal}}s [[BackFromTheDead restore him]], and when he goes to the city with the animals, the princess identifies him, and since he has the tongues of the dragon, he can prove the marshall a liar.
** Similarly in "[[http://www.mythfolklore.net/andrewlang/079.htm The Three Princes and their Beasts]]", where the prince had gotten tokens from the princess.
* In "[[http://www.mythfolklore.net/andrewlang/396.htm The Three Dogs]]", the king made the same promise; the hero killed the dragon and promised to return within a year to marry her, but a coachman made her promise to say that he had killed the dragon. The hero proved himself with his dogs and the teeth of the dragon.
* In "[[http://www.surlalunefairytales.com/pentamerone/7merchant1911.html The Merchant]]", the hero had killed the dragon on this promise. He had to throw the heads far apart to keep them from rejoining the body, but a peasant collected them and claimed to have killed the dragon. The princess recognizes his dog, and he can produce the tongues to prove his claim.
* Native American myth: {{Gender Flip}}ped, as the women had to describe an invisible hunter's appearance in order to marry him. The NaiveEverygirl correctly described him, while her stepsisters lied about his appearance.
** In another version, the moral here is about honesty -- the guy wants an honest bride, so he has his sister (the only one who can see him) vet the candidates by telling them that the right girl should be able to see and describe him while he's invisible. They all lie, making wild (and wrong) guesses at his appearance, until the heroine, who admits that she can't see him. He makes himself visible for her (or involuntarily becomes visible, due to the mystical power of truth-telling), so she's able to tell his sister what he looks like and passes the test.
* "Literature/{{Donkeyskin}}" is an odd instance in which the reader is supposed to side with the one setting the challenges, rather than the one trying to complete them. [[ParentalIncest Most readers will.]]
** As they will in [[Creator/TheBrothersGrimm Grimms']] "[[http://www.surlalunefairytales.com/donkeyskin/stories/allfur.html All-Kinds-of-Fur]]", and "[[http://www.surlalunefairytales.com/donkeyskin/stories/kingdaughter.html The King Who Wished Marry To His Daughter]]".
** Most will also agree with the heroine in "Literature/{{Catskin}}", although she only faced an ArrangedMarriage to "a nasty rough old man" there.
* "Literature/ThePrincessAndThePea".
* [[Creator/TheBrothersGrimm Grimms']] "[[http://www.grimmstories.com/en/grimm_fairy-tales/the_six_servants ]]" TheSixServants features an additional twist: Failure to perform the task set by the princess's [[EvilMatriarch evil mother]] would have their [[OffWithHisHead head cut off.]] The hero of the story prevails with the help of his six servants, mentioned in the title.
* Grimm again, with "[[http://classiclit.about.com/library/bl-etexts/grimm/bl-grimm-how6men.htm How Six Men Went Out Into the World]]"[=/=]"[[http://www.youtube.com/watch?v=oVi3T2abqoU The Six Who Went Far In the World]]", where the suitor must beat the princess herself in a race or be beheaded. Unfortunately, the princess is a dirty cheater.
* "[[http://en.wikipedia.org/wiki/The_Tale_of_the_Bamboo_Cutter The Tale of the Bamboo Cutter]]" has a challenge such as this.
* In "[[http://etc.usf.edu/lit2go/contents/1300/1305/1305_txt.html Hans, Who Made The Princess Laugh]]", (also known as "The Princess Who Couldn't Laugh") the king promises his daughter's hand in marriage to anyone who [[ExactlyWhatItSaysOnTheTin can make the princess laugh.]] Hans manages to make her laugh when he gets enough people stuck to him, forming a human chain.
* In ''Literature/BootsWhoMadeThePrincessSayThatsAStory'', anyone who gets the princess to say that his story is a story can marry her and get half the kingdom as well. Boots succeeds.
* In Creator/TheBrothersGrimm's ''Literature/TheGoldenGoose'', whoever gets the princess to laugh wins her.
* ''The Farmer's Clever Daughter'', another one from the Grimms' collection, the king sets impossible tasks to the heroine, and marries her when she succeeds.
* In ''Literature/EastOfTheSunAndWestOfTheMoon'', the heroine wins the hero from the troll bride by washing his shirt clean.
* In ''[[http://www.surlalunefairytales.com/eastsunwestmoon/stories/norroway.html The Black Bull of Norroway]]'', the heroine washes out the hero's shirt, which is the test for the bride.
* In Creator/AndrewLang's ''The Violet Fairy Book'', in "[[http://www.mythfolklore.net/andrewlang/055.htm The Frog]]", the old woman tells her sons to test their brides with flax.
-->''Do as you like, but see that you choose good housewives, who will look carefully after your affairs; and, to make certain of this, take with you these three skeins of flax, and give it to them to spin. Whoever spins the best will be my favourite daughter-in-law.'''
* In ''Literature/TheThreeAunts'', the queen mother retroactively declares that the tasks were proof enough of her domestic skils, and lets her marry the king. Whereupon the three aunts show up again to scuttle the need for her to try the work again.
[[/folder]]

[[folder:Fan Fiction]]
* ''FanFic/AGrowingAffection'': Hinata's grandfather (named Hyouta in this story) decides if Hinata is going to keep dating Naruto, she will have to prove she is a worthy successor to Hiashi [[spoiler: by defeating Neji]] and Naruto will have to prove he is a better suitor than the man Hyouta has chosen [[spoiler: a Jonin and a noble who is older than Hiashi]]. And when it looks like Naruto and Hinata have succeeded, he does some rules lawyering, resulting in a third challenge [[spoiler: Naruto vs. Hyouta which is definitely not what the old man was looking for]].
[[/folder]]

[[folder:Film]]
* A variant in ''LoveAndBasketball'' in which the heroine asks this test of the hero. She assumes that if he wants her he will let her win. [[spoiler:As it happens the hero wins but marries her anyway.]]
* The title character in ''Film/{{Shrek}}'' saved princess Fiona from a castle situated [[ConvectionSchmonvection over a smoldering volcano]]. She was O.K. with marrying him until finding out he was an Ogre, and he was just working as a champion for Lord Farquaad. In keeping with the whole theme of subverting fairy tales in the movies, she [[spoiler:turns into an ogre as well and marries Shrek anyway]]. On top of that, [[spoiler:the (female) dragon who was guarding the princess ends up with Shrek's sidekick Donkey]].
** It's implied that Fiona was more upset over Farquaad sending what amounted to a courier to get her, rather than fetching her himself. Even then, she might have accepted it if it hadn't become very clear that the reason he didn't go and rescue her wasn't because he wasn't able to do so, but because he ''couldn't be bothered'' to follow fairy-tale traditions.
[[/folder]]

[[folder:Literature]]
* Creator/JRRTolkien's Middle-earth, twice:
** In ''Literature/TheSilmarillion'', the Elvenking Thingol tries to get rid of his daughter Lúthien's ''human'' suitor Beren by tasking him to get one of the holy Silmarils from the world's {{Satan}}-[[BigBad equivalent]] (who wears it constantly), thinking Beren'll either back off, fail, or die trying. Beren accepts the task, but in a variation on the usual trope, his lover Lúthien is instrumental to the quest; she follows him, repeatedly saves his ass, and vanquishes his much more powerful foes. Not that Beren's a slouch -- he's a {{Badass}} who accomplishes quite a bit himself along the way.
*** He also uses ExactWords to pull it off. He was told to return with a Silmarili in his hand, and he did so. Even though the hand was in the stomach of the werewolf Carcharoth.
** In ''Literature/TheLordOfTheRings'', Elrond will only let his daughter Arwen marry Aragorn if he's King of a reunited Arnor and Gondor and Sauron is gone; quite sensible, as of course Elrond doesn't want his daughter to stay behind on a Middle-earth ruled by Sauron, so he won't let her unless Aragorn helps make it a safer place to live.\\
\\
As Elrond [[ParentalSubstitute raised Aragorn]] as a foster-son, it's pretty strongly implied that he badly wants to make sure that Aragorn fulfills his destiny, so he's also using the useful coincidence fate dealt him to do so. And unlike their mutual ancestors Beren and Lúthien, Aragorn and Arwen seem okay with the condition set on their marriage. Naturally Aragorn wants to save the world ''anyway'', and the allusion to Beren implies he's lucky it's a relatively easier prospect.
* In Creator/JamesThurber's ''Literature/The13Clocks'', the Duke sets impossible tasks to the princes who want to marry his niece Saralinda.
** In another Thurber tale the princess herself sets the tasks, giving impossible ones to the two elder princes and an easy one - that turns out not to be ''quite'' so easy - to the youngest prince. Guess which one she really likes.
* In Creator/EdgarRiceBurroughs's ''Literature/TheMonsterMen'', the MadScientist regains his wits after [[MadScientistsBeautifulDaughter his daughter]] and promises his assistant that he can marry her if he rescues; as the assistant is lying and one of the villains of the piece, he does not succeed in the end, where the scientist agrees that the man who has rescued her can certainly court her.
* In Creator/DianaWynneJones's ''Literature/PowerOfThree'', the Chief of Otmound says that Gest can only marry his daughter Adara if he completes three tasks first: one, spend an entire day answering riddles the Chief asks him (Adara tells him the answers); two, move a massive stone from the top of Otmound (Gest [[spoiler:gets the Giants to help]]); and three, bring back a Dorig collar, made more complicated by the fact that Adara refuses to marry a man who would kill a Dorig ([[spoiler:luckily, Gest has Dorig friends]]). The Chief wanted Gest to remain on friendly terms with him without actually refusing his suit--hence the challenges. Unfortunately, Gest got help.
* In Creator/AndrewLang's ''Prince Prigio'', the king has promised his niece's hand in marriage and the kingdom to whoever brought him the head of a monster. The monster is killed by his rather annoying son Prigio, but the head is brought by a servant. Prigio persuades the king that obeying the letter of his promise would infringe on the right of royalty to say other than what they mean. However, being in love with another woman, he refuses to marry his cousin -- who had been engaged to and in love with his dead brother, but finds being refused rather insulting. Fortunately, Prigio revives his younger brothers, and so they agree to let him marry his love and the niece to marry his brother.
* Name-checked in LoisMcMasterBujold's ''[[Literature/VorkosiganSaga A Civil Campaign]]'', wherein Miles Vorkosigan is having trouble courting the lady of his dreams. She discusses him with his former boss, who tells her: "Do you know all those folk tales where the count tries to get rid of his only daughter's unsuitable suitor by giving him three impossible tasks? ... [[TheDeterminator Don't ever try that with Miles]]. [[GuileHero Just... don't."]]
* ''Literature/{{Stardust}}'': Victoria demands that Tristran bring her a falling star. He finds the star, which turns out to be a MacGuffinGirl, and falls in love with her instead. (As it turns out, Victoria was just teasing him and was already engaged to someone else.)
** Of course, the movie made both Victoria and her suitor a ''bit'' less honorable than in the book, wherein Victoria thought Tristran dead and was all set to marry her other beau when Tristran returned - and she was willing to honor her promise to him regardless. She was rather distressed, to be quite honest. Not that it was idle characterization, either: the marriage had a rather startling effect on a certain prophecy.
* The main plot of ''AllsWellThatEndsWell'' is a gender- and time-reversed variant. Helena is married to Bertram by her choice and against his will. He runs away to Florence, saying that he'll only accept her as his wife if she can get his family ring off his finger and present him with his own child. Of course, she does.
* In ''[[Creator/WilliamShakespeare The Merchant of Venice]]'', Portia's suitors must solve a puzzle in order to marry her, and if they answer incorrectly they're barred from marrying ''anyone''.
* In ''What is the Name of This Book?'' Raymond Smullyan uses this many times as the framing device for logic problems which the suitor (and the reader) must solve.
* In RobinHobb's ''[[Literature/RealmOfTheElderlings Fool's Fate]]'', the princess's family will only let the prince marry her if he can lay the head of the dragon on their mantel. He goes on a quest with some others to kill the dragon and fulfill this, but events transpire such that they realize that they really shouldn't kill the dragon. However, [[spoiler: he fulfills the condition anyway by convincing the dragon to come over and rest its head on the mantel]].
* In Susan Dexter's ''The Prince of Ill-Luck'', the hapless protagonist stumbles into one of these; he only rode his horse up a hill of glass to claim a golden ring because, well, golden ring! Only afterward does he realize that victory is attached to a princess who doesn't want to marry ''anyone'', thanks.
* In Anthony Armstrong's short story "The Warlock's Daughter", a king assigns his daughter's suitors the task of finding water in a desert. The protagonist, having encountered the title character, uses a charm she gave him to summon her and asks her to create a river. She does, but having seen her, the hero decides he'd rather marry ''her''. She's a little surprised, but agrees. The princess, who didn't like the whole "Do X and marry my daughter" thing the king came up, orders her suitors to find the hero and capture him in exchange for her hand, then marries a knight she'd had her eye on once they're all out of the kingdom.
* Creator/PatriciaAMcKillip's ''Literature/TheRiddleMasterTrilogy'' begins this way. The Prince of Hed (an island prinicipality so small that even the prince is just a farmer) went in secret to challenge a fearsome ghost to a riddle-contest - his life wagered against the ghost king's crown. He won the contest that princes and sages had died in for centuries and went home, unaware that by winning Peven's Crown he had won the right to marry his best friend's sister, Princess Raederle "the second most beasutiful woman in the Three portions of An". (Mildly subverted in that Raederle's father Mathom had SecondSight and knew who would win the game before he made the challenge.)
** This is all backstory, mind you. And Morgan, the prince, does not go to collect his princess, which requires her to go searching for him, which in turn drives much of the second book of the trilogy.
* In Creator/BruceCoville's ''The Dragonslayers'', the king promises that whoever can slay the dragon may marry his daughter. The only person who will go is the ancient squire Elzar. The princess, naturally not liking this at all, pulls a SweetPollyOliver and sets off to slay it herself.
* The basis of the romance subplot in Literature/TheEdge novel ''On The Edge''. Rose has powerful magic but no pedigree, and as such would be treated as a baby-making machine by any noble she married. Declan proves that he's powerful enough to take her by force, and then offers her a deal. "The traditional solution" to their dilemma is three engagement challenges. If he loses any of them, he will leave and never bother her again; if he wins them all, she must come with him and be pleasant and agreeable. Rose accepts. [[spoiler: It develops that Declan came up with this plan on the spot as a reasonable excuse for him to be hanging around the area, where he has a mission to complete. In short order it's more than a cover, however.]]
* In the MagicTheGathering novel ''The Brothers' War'', the warlord ruler of the city of Kroog and the surrounding nation of Yotia wants somebody "strong" to carry on his legacy, so he sets up one of these. He puts a giant statue in an arena - far too heavy for any single person to lift - and promises his daughter and kingdom to the man who can carry it to the other side. GadgeteerGenius Urza succeeds by building a Magitek robot to do it for him, and the king is unusually willing to keep his side of the bargain. Amusingly, Urza, being a ChasteHero and a borderline [[{{Asexuality}} asexual]], is far more interested in the kingdom's supply of magical powerstones than its stunningly beautiful princess; she ends up falling for ''him'' long before he develops feelings for her.
* A "PostModern Fairy Tale" book had the story of a rather butch princess whose parents put on an engagement challenge for her. If I recall correctly, the competing princes had to be stronger, smarter, and ''taller'' then her (she's kind of a HugeSchoolGirl), and the only guy who qualified was a [[NoodlePeople Noodle Person]] she let win their ''wrestling match'' (well, how else could they prove they're stronger?) because she was afraid of hurting him. Later that night, the princess [[MeetCute meets cute]] with one of the visiting princes' helicopter pilots (she's a big helicopter buff) and while he is her intellectual equal he's [[HugeGuyTinyGirl neither as tall nor as strong]] as she is (she doesn't care, but her parents might, considering their criteria). [[spoiler: It turns out that not only is he Noodle Guy's pilot but he's actually the prince - he and Noodle Guy switched places because he (the prince) thought the challenge was silly. Naturally, the prince and princess get a HappilyEverAfter.]]
** That would be ''The Wrestling Princess''. Awesome book. One of the other stories in it, "Georgiana and the Dragon", features the titular princess rescuing a prince from a dragon, also as one of these.
* In "The Sleeping Beauty" one of TalesOfTheFiveHundredKingdoms, the Princess Rose's hand is the prize of a great tournament that many princes have traveled to compete in. The thing is, the reason the tournament is being held is the princes being there prevents the kingdom from being attacked until it's strong enough to discourage invasions by other means. Furthermore, the challenges are designed to be completely non-lethal and entirely relevant to ruling the kingdom, and the GenreSavvy Princess Rose and her guardian are hoping that narrative causality will make sure that the winner ends up being someone Rose can love, as well as a good king.
* In ''Literature/CodexAlera'' every Marat marriage involves on of these. However, since each individual challenge is set by the Marat woman in question the nature of the challenge can vary wildly based on the abilities of the prospective husband, and whether she wants to marry him or not. [[spoiler: In the final book Kitai names her challenge to Tavi as killing the Vord Queen.]]
* This trope forms the backbone of [[http://en.wikipedia.org/wiki/Culhwch_and_Olwen How Culhwch Won Olwen]], one of the oldest surviving works of Welsh literature. Culhwch is [[{{Curse}} cursed]] by his WickedStepmother that he can [[ParentalMarriageVeto marry no-one]] but the daughter of Ysbaddaden the Giant. Ysbaddaden claims that he cannot prepare for the ceremony until Culhwch hunts the [[FullBoarAction giant boar Twrch Trwyth]] and retreives a [[PlotCoupon comb, scissors and razor]] from his hair. But he can only be tracked by a certain hound, and the leash can only be made by a [[LivingMacGuffin certain hero]] [[DismantledMacGuffin and held by another...]] the job ultimately involves over forty different tasks and the aid of no less than KingArthur and his warband.
** And then, once they've done all that, Ysbaddeden's nephew Goreu [[ShaggyDogStory beheads the giant before the marriage]] in vengeance for the deaths of his brothers.
* In another FracturedFairyTale, the princess is the one who set the challenges - which include such things as keeping up with her in an all-night roller-disco, and other feats of endurance and proofs that they share her interests (or are at least willing to tolerate them for her sake). Finally, one prince manages to succeed at all the tasks she sets (while other, lesser princes drop like flies around him) and she rewards him with one last task: kiss her. He does [[spoiler: and he turns into a frog. Her reaction: "Darnit, that's the hundredth time that's happened!" She's been trying to weed through the suitors to try and find one who won't turn into a frog when she kisses him!]]
* Subverted in ''Literature/TheLegendsOfEthshar'' novel ''With a Single Spell'' where the erstwhile dragon-slayers were promised a bag of gold and a princess for defeating the dragon. Upon returning successfully, one of the heroes tries to refuse the princess and take the gold only to find that it's a package deal. There are too many princesses and the gold is her dowry.
* The ''Franchise/DoctorWhoExpandedUniverse'' short story "The Trials of Tara", a pastiche of Shakespearian tropes, has [[Recap/DoctorWhoS16E4TheAndroidsOfTara Queen Strella of Tara]] set tasks for her suitors to avoid marrying any of them, since she believes that King Reynart is still alive.
* Parodies in ''Discworld/GuardsGuards'', in which [[BarbarianHero barbarian heroes]] refuse to try and slay the dragon plaguing Ankh-Morpork unless they get "the king's daughter's hand in marriage and half the kingdom", despite the fact that Ankh-Morpork is a republic and its Patrician is unmarried.
** He's got an aunt though. And a dog. One of the heroes asks what kind of dog before deciding "Nah."
* A double example occurs in the ''{{Nibelungenlied}}'' - Siegfried will only get her brothers' permission to marry Kriemhild if he helps the eldest, Gunther, to woo Brunhilde. And who wants marry Brunhilde has to defeat her in a three-part athletic contest or die. Using his ''Tarnhelm'' (helmet of invisibility and shape-changing), Siegfried helps Gunther to win by cheating. ItDoesNotEndWell.
* One springs up unexpectedly in Creator/JohnMoore's ''Literature/HeroicsForBeginners''. When the Ancient Artifact Model Seven is stolen by Lord Voltmeter, it immediately becomes clear to everyone that Princess Rebecca's hand must go to the man who retrieves it. There's no other way. Which is a problem for Prince Kevin, since Prince Logan--and his army--is clearly the most qualified man to retrieve the artifact. Kevin has only his copy of ''The Handbook of Practical Heroics'' on his side.
* In the backstory of RobinMcKinley's ''Literature/{{Deerskin}}'', the heroine's grandfather was highly possessive of his daughter, and set fearsome challenges to her suitors, that no man might take her from him.
* The Terry Pratchett short story "The Prince and the Partridge" featured a challenge to present to the princess a gift that can dance, leap, play tunes, make a beat, carry pails, hiss, swim, lay eggs, can be worn on one hand, sing, cackle, coo, waggle its eyebrows and is good to eat. The titular prince and partridge ultimately work out that the gift doesn't necessarily have to be one item, and so, on the twelfth day of Christmas, Prince Albert presented to his true love [[spoiler:Twelve ladies dancing, eleven lords a leaping, ten pipers piping, nine drummers drumming, eight maids a milking, seven swans a swimming, six geese a laying, five golden rings, four calling birds, three french hens, two turtle doves, and a partridge in a pear tree]].
[[/folder]]

[[folder: Live Action TV ]]
* ''Series/MontyPythonsFlyingCircus'' spoofed this with a sketch in which a king keeps telling his daughter's courtiers to go to the tallest tower in the land and hurl themselves off it. If they survive they can marry the princess. All of them do it, not one of them survives, until eventually the queen gets so fed up with this that she makes him stop it. The final courtier's impossible task is to go to the shops and get the king a packet of cigarettes. Ironically, he fails as well; he gets hit by a bus on the way home.
** In an alternate version of the sketch, the prince succeeds, but a better-looking prince shows up and slays a 'dread dragon' (a plastic toy on a string), at which point the king hands him the engagement. This causes the rejected prince to get an evil witch to curse everyone[[note]] including herself, which she realises too late[[/note]] in revenge.
* ''Series/FreeSpirit'', a 1989 sit-com, had main character Winnie Goodwin (a witch)'s fiancee (a warlock) show up after a courtship that spans 150 years. He had to cross the Atlantic in a day, and capture a girl's smile without using magic. Modern tech helps him beat most of her father's challenges.
* ''Series/TheGoodies'' spoofed the trope in the episode "Scatty Safari" by having "an anonymous Queen" offer the hand in marriage of her eldest son to whoever purged the land of its plague of Rolf Harrises.[[note]] The eldest son of said "anonymous Queen" was apparently interested in appearing in the episode as himself, but Palace security voted down the idea.[[/note]]
** In another episode Tim wins the hand of his bride, but it's [[ExactWords literally the hand]]. Graham is shown snogging with the rest of her, except for the legs which are given to Bill.
[[/folder]]

[[folder:Religion and Mythology]]
* ''Literature/TheBible'' naturally enough has at least one case of this, with David having to bring Saul back [[TwentyBearAsses the foreskins of 100 Philistines]] to prove himself worthy of Michal's hand (and not coincidentally, Saul's throne). Some versions claim he brought back twice that number in order to show Saul up.
** [[CrowningMomentOfFunny Hilariously played for laughs]] in Joseph Heller's ''God Knows'' where David spend several pages calculating how many warriors it will take to hold down each Philistine so [[GroinAttack the mohel can circumcise him]], until Saul takes pity on him and explains that it isn't actually necessary for the Philistines to survive the operation and he will, in fact, accept foreskins that haven't actually been detached yet.
** Also Judges 1:12:
--->"And Caleb said, He that smiteth Kirjathsepher, and taketh it, to him will I give Achsah my daughter to wife."
** The Book of Tobit (not to be found in Protestant Bibles) features a woman cursed with a demon so that [[CartwrightCurse the men who try to marry her don't survive the wedding night]]. In a subversion of the trope, her parents are only too eager to marry her off to a young man willing to give it a try -- the seven previous suitors didn't make it. With the help of the angel Raphael, Tobias banishes the demon [[spoiler: by putting fish parts in the fire and saying his prayers]] and survives til morning.
** Older still: In Genesis, Laban has Jacob work for a period of 7 years (in lieu of a more conventional bride price) for his daughter Rachel. Then, he switches her out for [[ChristmasCake her sister Leah]] under the bridal veil, on the grounds that he didn't think it was appropriate for the younger daughter to be wed before the elder. Daddy agrees that he'll still give Jacob the girl he ''really'' wanted...in exchange for another 7 years of servitude.
* According to a Jewish legend, Reb Eisele Charif challenged all the young yeshiva students with a difficult Talmudic question, declaring that the one who answered correctly could marry his daughter. No one came up with a good answer, so he packed up and left. However, on the outskirts of town he noticed he was being chased by one young scholar, who admitted that despite failing the challenge he still wanted to know the answer to the question. [[SecretTestOfCharacter He was allowed to marry the daughter]].
* GreekMythology tells of how Atalanta made a deal with her father so she would only marry the man who could outrun her in a race (she was a really, really fast runner). Some versions also held that losers of the challenge would be killed. Hippomenes ([[DependingOnTheWriter or Melanion]]) won her by throwing golden apples (kindly donated by [[LoveGoddess Aphrodite]]) at her feet during the race, which she stopped to pick up. OlderThanFeudalism.
* Standard practice in ancient India, so of course it shows up in the ''Literature/{{Ramayana}}'' and ''{{Mahabharata}}''. In both cases, they're occasions not only to get the hero(es) with his future wife but also to establish just how awesome they are. In the ''Ramayana'', Rama picks up Shiva's personal bow, tries to string it, and ''snaps'' it; most people and some lesser deities aren't even able to lift it. And in the ''Mahabaratha'', Arjuna and Karna both shoot the eye of a wooden fish atop a pole by its statue, and Arjuna goes on to be TheHero while Karna becomes TheDragon.
* In the 19th-century Finnish epic ''Literature/TheKalevala'', EvilMatriarch Louhi of Pohjola likes to give her daughters' potential suitors nigh-impossible tasks.
* One of the points where Germanic and [[RussianMythologyAndTales Russian]] heroic legend meet in ''Thidrekssaga'' is when Hartnit (or Ortnit), who ruled in Novgorod (Holmgard) and supposedly son of the hero [[TheBigGuy Ilya Muromets]], won a {{Valkyrie|s}} bride by fighting against a giant. He was later killed by a dragon, but his brother avenged him and married the widow -- which probably counts too.
* When Cu Chulainn asked for Emer's hand in ''[[CelticMythology The Wooing of Emer]]'', Emer told him via a very dense riddle that, as Forgall the Willy would almost certainly refuse to let his daughter marry him, Cu Chulainn wasn't allowed to [[UnusualEuphemism "come to her plain"]] until he defeated one hundred men at every ford from Ailbine to the Boyne, slain her evil shapeshifting aunt, salmon-leaped across three ramparts to reach her, killed each of her three brothers' teams of guards while leaving the brothers themselves untouched, and personally carried both her and her possessions out of her father's castle. After some training under the warrior woman Scathach, he did exactly that.
[[/folder]]

[[folder: Tabletop Games ]]
* In the ''MagicTheGathering'' tie-in novel ''The Brothers' War'', the Warlord of Kroog, searching for a powerful warrior to wed his daughter, decrees that whoever can move a giant jade statue from one end of the palace courtyard to the other will win the hand of Princess Kayla. [[GadgeteerGenius Urza]] completes the challenge by building an automaton with enough power to lift the statue.
[[/folder]]

[[folder:Theatre]]
* Gender-flipped in ''OnceUponAMattress'': Queen Aggravaine has declared that nobody in her kingdom can get married until her son Dauntless does. Unfortunately, she keeps setting impossible tests for the Princesses because she believes that nobody is good enough for him.
* In ''Theatre/{{Turandot}}'', if one wanted to marry the titular princess he had to correctly answer three questions asked by her; failure resulted in beheading.
* In ''Die Meistersinger von Nürnberg'' by Creator/RichardWagner, Walther must win the [[strike:Nuremberg's Got Talent]] time-honored singing contest before he gets the hand of Eva.
* In the song "Princess of Pure Delight" from ''LadyInTheDark'', a King demands his daughter's suitors answer the riddle, "What word of five letters is always spelled wrong?"
* ''Theatre/TheMerchantOfVenice'': When Portia's father died, he set up a lottery--anyone who wants to win Portia's hand must be given the choice of three chests, gold, silver, and lead. If a man choses the one that contains her picture, he gets to marry her immediately--but if not, not only does he have to leave her forever, he's bound by oath never to marry anyone else.
** Played more nastily by Shakespeare in ''Theatre/PericlesPrinceOfTyre'': Antiochus decrees his daughter's suitors must attempt to answer a riddle, and if they fail they will die. Since the solution of the riddle is "Antiochus is in an [[ParentalIncest incestuous]] relationship with his daughter", those who answer it correctly [[MortonsFork will also die]].
* In Creator/AAMilne's ''The Ugly Duckling'' the test is a rediculously easy riddle: "What is it which has four legs and barks like a dog?" [[spoiler:A dog, of course.]] But because the Princess is [perceived to be] so very ugly everyone always guesses wrong.
[[/folder]]

[[folder: Video Games ]]
* In ''VideoGame/{{Terranigma}}'', the King of Loire gives the hand of the mute princess to the man who makes her speak again. However, there is a twist: [[spoiler: she's not really his daughter but a child from a village that he destroyed in search of the village treasure. The King only wants her to speak again so she can tell him where the treasure is.]]
* In ''VideoGame/DragonQuestIV'', a king offers his daughter's hand in marriage to the one who wins a fighting tournament. His daughter is already in love with someone who isn't a wonderful fighter, unbeknownst to daddy. What's worse, the front-runner in the tournament is viciously cruel. In the end, both king and princess plead with the tomboyish Alena to enter the tournament; same-sex marriage is apparently unheard of, so a woman winning the tournament would cause the whole marriage thing to be called off.
** In the original version, it's just the princess who asks Alena to help her. And when Alena wins, the king briefly jokes about marrying her instead. [[CuteBruiser Considering how clearly she could make her disagreement with that idea known]], it's no surprise he backs off.
* Speaking of ''VideoGame/DragonQuest'', ''VideoGame/DragonQuestV'' features an Engagement Challenge for the hand of Nera, along with a shield the hero needs as a wedding present. You have to complete the challenge and ''can'' marry Nera, but Nera's father is willing to let you marry [[VictoriousChildhoodFriend Bianca]] if you so desire and still get the shield.
** In the DS Remake, you can also choose to marry [[ThirdOptionLoveInterest Nera's sister Debora]], but no matter what, you'll always get the Zenithian Shield. Conveniently, [[spoiler:all three girls are descendants of the previous ChosenOne, thus allowing your son to be the new ChosenOne later in the game]].
* Variation in ''VideoGame/OdinSphere''. In order to obtain the MacGuffin, Demon Lord Odin requested his former enemy, Oswald the Shadow Knight, to slay a dragon. He offered him a castle as a reward at first, but Oswald wasn't interested until Odin decided to offer his daughter Gwendolyn. Having [[LoveAtFirstSight fallen in love at first sight with her]] earlier, he decided to accept the task, though not without being skeptical at first.
* ''VideoGame/MapleStory'' treats this like a quest. And like any quest in ''VideoGame/MapleStory'', requires you to collect TwentyBearAsses to earn a Proof of Love. Males have to earn 6 of those Proofs of Love (And have the materials to make the ring), while females have only have to earn 2. That's as far as you can get for free, the actual wedding is going to cost you real money.
* The [[AllThereInTheManual (unstated in the game)]] backstory of Emperor Mateus Palamecia from ''VideoGame/FinalFantasyII'' says he once did this with his daughter, declaring that anyone who can reach her at the top of a tower filled with dangerous monsters would have her hand in marriage. Nobody succeeded in rescuing her the fair way, but a bold adventurer just used an airship to fly up to her room and rescue her. Being bested by this loophole caused the Emperor to be consumed with rage, and he invaded and burned down the adventurer's hometown, [[StartOfDarkness finding he very much enjoyed conquering in and of itself.]]
* Should you choose to marry Mana in ''[[VideoGame/RuneFactory Rune Factory 2]]'', her final request will involve [[OverprotectiveDad fighting her crazy father.]]
** In ''VideoGame/RuneFactory3'', your chosen bride will disappear the morning of your wedding. You'll have to fight [[spoiler:Aquaticus, Dragon God of Water]] to get her back.[[note]]This turns out to be the final part of Aquaticus' master plan to revitalize the Sharance Tree and save the land from ruin: Proving your love is strong enough that you'd be willing to take on a god for your bride.[[/note]]
* Present in the {{Backstory}} of ''VideoGame/WishBringer'': the evil Queen Alexis sent all of her daughter Morning-Star's suitors on Love Quests that invariably get them killed, then declares that no man is worthy of the princess and Morning-Star will be forever unwed. [[DownerEnding Morning-Star dies with all her wishes unfulfilled and her heart becomes the wish-granting stone Wishbringer]].
[[/folder]]

[[folder:Web Comics]]
* The [[http://www.drowtales.com/mainarchive.php?sid=8319 'Flower Queen']] of ''{{Drowtales}}'' did not wish to mate with a drow, the newest forming race in their underground kingdom and the only remaining race that had suitable males for her to mate with. To avoid this, she set up a challenge that anyone who wished to mate with her most first bring her the most beautiful flower in the world, expecting this to be an impossible task. The Flower Knight was [[{{Determinator}} determined]] to prove her wrong.
* In ''Webcomic/{{Sinfest}}'', Monique will upgrade Slick not to a fiancee or even boyfriend, but a "good friend" if he [[http://www.sinfest.net/view.php?date=2005-06-30 defeats the Devil]], [[http://www.sinfest.net/view.php?date=2005-07-01 creates world peace, feeds the hungry and treats her like a princess.]] Slick observes that the Devil offers a better deal.
** [[http://www.sinfest.net/view.php?date=2007-06-03 He tries again later. No dice.]]
[[/folder]]

[[folder: Western Animation ]]
* This idea was played with on ''WesternAnimation/TheSimpsons'' when Apu gets caught cheating on Manjula. He lays the challenges on ''himself'' in an attempt to win her back, which works wonders but also causes a lot of marital problems for all the other guys in town.
* On ''BuzzLightyearOfStarCommand,'' [[BadassPrincess Mira]] [[InvokedTrope invokes this]] when she is [[YouHaveWaitedLongEnough suddenly reminded of her]] ArrangedMarriage. She challenges her foppish fiancé to get through [[SpacePolice Space Rangers]] Basic Training, knowing that a pampered blueblood like him could never--[[GilliganCut oh wait]], he winds up becoming [[RuleOfFunny the most decorated cadet in history]]. Fortunately, she eventually gets it called off, and the fiancé decides that he would rather go back to the Rangers than settle down anyway.
* The ''WesternAnimation/HeManAndTheMastersOfTheUniverse1983'' episode "The Return of Granamyr" had a variation. A dragon had fallen in love with a human girl. Her wizard father consented to the union and offered to make him human if he could pass his test, but the test was designed for humans, so He-Man was volunteered to be his substitute. He-Man had to enter a maze and retrieve a silver apple from a tree in the center. In the maze, his path gets blocked by a wall of fire, but He-Man realizes it is an illusion and continues. Then, he gets confronted by a beautiful woman who offers him the apple, but He-Man remembers the apple is on ''the tree'' and dismisses that illusion. The final obstacle was a centaur who demanded a test of strength. He-Man was unwilling to fight him, so he proposed a tug-of-war, which the centaur accepted and lost. On the way back, He-Man gets attacked by an evil wizard who wanted the girl for himself, but he quickly defeats him and returns with the apple to win the challenge.
* Hilariously invoked in one of RockyAndBullwinkle's [[FracturedFairyTale Fractured Fairy Tales]]. A young man is told by the king that in order to marry the princess, he must successfully complete one task. The youth points out that this is unusual, as three tasks is the regular requirement.
-->'''King''': Well, since no one's ever come back from the first task, I've forgotten the other two.
** That show had ''at least'' two other FracturedFairyTale sketches poking fun at the trope.
[[/folder]]

[[folder: Real Life ]]
* In early 19th-century Okinawa a woman named Yonamine Chiru insisted that any would-be-suitors had to best her at martial arts. She defeated everyone until [[{{Badass}} Bushi Matsumura]], one of the founders of modern karate and among the most fearsome fighters in Okinawan history, managed to narrowly defeat her and so won her hand. [[CrowningMomentOfAwesome My, oh my.]]
[[/folder]]
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