Engagement Challenge

"The Fairy Godmother: Ah, but this is no ordinary Science Fair! 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."

- Girl Genius, Cinderella Parody

"You want to marry my daughter? Prove yourself worthy; kill yonder dragon," the King proclaims, and the heroes gather to win the fair damsel's hand - a Fairy Tale 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 princess's hand.
 * The king uses it to lure heroes to help the kingdom, which is sometimes a Gender Flip.
 * It features as a way to have the prince or princess rescued; this is more often a Gender Flip, but the precise challenges tend to differ according whether it is a hero or a heroine challenged, as the princess is more often Chained to a Rock and the prince deathly ill and in need of magical healing.
 * The king does not want to see her married off and resorts to this as a form of Parental Marriage Veto. The challenge is either impossible or deadly.

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

If the king decides after all that fulfilling the challenge doesn't make you worthy (frequently if he didn't realize it would be Rags to Royalty), Dude, Where's My Respect? or Moving the Goalposts may ensue; the opening Engagement Challenge was open to all comers, but the subsequent ones only to the peasant who succeeded—and quite frequently an Impossible Task. 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 something he does want done but will probably kill him.

Another problem is often a 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 will tell the truth if the the hero is there to protect her..

These days there are usually complications. Sometimes, the Evil Chancellor set up the challenge, tricking the king into getting some naive hero to collect his 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 Accidental Marriage which can lead to some seriously miffed princesses. Of course, if the hero does want the marriage, the more modern 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 No Man of Woman Born level conditions, Prophecy Twist-style wrangling may occur.

The Fractured Fairy Tale often plays with this. The Scheherazade Gambit enters into some variants where it is a test of wits rather than a test of courage.

Anime And Manga

 * In Kenichi: The Mightiest Disciple, Elder tells Kenichi that he would only allow him to propose to Miu (Elder's granddaughter) if Kenichi beats him in a fight. Elder is known as "the man without enemies". Think about it.
 * It's even better in Japanese "man without enemies" is the literal definition of the word Invincible.
 * In Kimagure Orange Road, 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 Honey Honey no Suteki na Bouken, 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 Tokyo Mew Mew, 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, 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 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.

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).
 * Actually I heard it was about a dying man asking for help with his funeral, the seamless shirt being what corpses are buried in.
 * 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 (Child Ballad #2) has an elf or a Dirty Old Man 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 Child Ballad #47 "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.

Comics
"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."
 * Erstwhile poses one to a young girl in "The Farmer's Clever Daughter".

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.
 * This editor read a different version of this folktale. In it, the task was to make the princess speak. The hero succeeds by conversing with a candlestick, causing the princess to ask him if he's mad for talking to a candlestick. While the hero doesn't behead the princess here, he refuses to marry her and tells her off for deliberately keeping silent even when doing so meant many well-intentioned men's deaths.
 * The man who discovered what happened to the Grimms' "The Twelve Dancing Princesses" was entitled to marry one of them.
 * "Jesper Who Herded the Hares" brings the pearls the king demanded. The king doesn't approve of Jesper and starts piling up the tasks.
 * "Katie Crackernuts" demands to marry the ill prince before she stays by his bed for a third night.
 * "Molly Whuppie" having two older sisters, and the king three sons, she carries out three challenges, marrying off each pair.
 * The "Princess on the Glass Hill" could be won only by a man who climbed the hill.
 * In "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 "The Serpent", a snake wants to marry a princess; her father demands three Impossible Tasks, but the snake succeeds, and the king reluctantly gives him the princess's hand. The snake is revealed to actually be a prince under a curse, but when the King 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 "Seven Foals" all day.
 * In Grimms' "The Two Brothers", the king has promised his daughter to anyone who rescues her from the dragon; after the huntsman kills the dragon, the marshall cuts his head off while he sleeps, but his Talking Animals 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 "The Three Princes and their Beasts", where the prince had gotten tokens from the princess.
 * In "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 "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 Flipped, as the women had to describe an invisible hunter's appearance in order to marry him. The Naive Everygirl 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.
 * "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. Most readers will.
 * As they will in Grimms' "All-Kinds-of-Fur", and "The King Who Wished Marry To His Daughter".
 * Most will also agree with the heroine in "Catskin", although she only faced an Arranged Marriage to "a nasty rough old man" there.
 * "The Princess and the Pea".
 * Grimms' "The Six Servants" features an additional twist: Failure to perform the task set by the princess's evil mother would have their head cut off. The hero of the story prevails with the help of his six servants, mentioned in the title.
 * Grimm again, with "How Six Men Went Out Into the World"/"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.
 * "The Tale of the Bamboo Cutter" has a challenge such as this.
 * In "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 can make the princess laugh. Hans manages to make her laugh when he gets enough people stuck to him, forming a human chain.
 * Subverted in an old joke where a very rich man calls all his daughter's gold-digging suitors together and confronts them with a swimming pool full of sharks. The first man who has the courage to swim across the pool will receive her hand in marriage. After a long pause where nobody goes for it, suddenly there is a loud splash and one of the suitors is in the pool swimming frantically for his life. At the end the man congratulates him and says 'You must really want to marry my daughter, young sir.' -- to receive a reply of 'The only thing I want is the name of the sonofabitch who pushed me into the pool!'

Film

 * Shrek saved princess Fiona from a castle situated 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 . On top of that,.
 * 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.
 * A variant in Love and Basketball in which the heroine asks this test of the hero. She assumes that if he wants her he will let her win.

Literature
""And Caleb said, He that smiteth Kirjathsepher, and taketh it, to him will I give Achsah my daughter to wife.""
 * JRR Tolkien, twice:
 * In The Silmarillion, Thingol tries to get rid of Lúthien's suitor Beren by tasking him to get one of the Silmarils from the Big Bad, thinking he'll either back off, fail, or die trying. Beren accepts the task, but in a variation on the usual trope, it is his lover Luthien who is instrumental to the quest; she follows him, and continually saves his ass and vanquishes his much more powerful foes.
 * In The Lord of the Rings, Elrond states to only agree for Aragorn to marry Arwen if he's King of a reunited Arnor and Gondor and Sauron is gone; quite sensible, as those are the ingredients of a save and secure future. Naturally Aragorn is planning to do this anyway, and the allusion to Beren implies he's lucky it's a relatively easier prospect.
 * And as Elrond raised Aragorn as a foster father, it's pretty strongly implied that he's only setting the condition because he badly wants to make sure that Aragorn fulfills his destiny, and he's just using the useful coincidence fate dealt him to do so.
 * Also unlike their mutual ancestors Beren and Luthien Aragorn and Arwen seem okay with the condition set on their marriage.
 * Elrond of course does not 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.
 * In James Thurber's The 13 Clocks, 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 Edgar Rice Burroughs's The Monster Men, the Mad Scientist regains his wits after 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 Diana Wynne Jones's Power of Three, 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 ); 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 . The Chief wanted Gest to remain on friendly terms with him without actually refusing his suit—hence the challenges. Unfortunately, Gest got help.
 * In Andrew Lang'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 Lois McMaster Bujold's 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? ... Don't ever try that with Miles. Just... don't."
 * Stardust: Victoria demands that Tristran bring her a falling star. He finds the star, which turns out to be a MacGuffin Girl, 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 All's Well That Ends Well 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 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 Robin Hobb's 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,.
 * 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.
 * Short story called 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.
 * Patricia A. McKillip's Riddlemaster Trilogy begins this way. The Prince of Hed (an island principality 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'd won the right to marry his best friend's sister, Princess Raederle, "the second most beautiful woman in the Three portions of An". (Mildly subverted in that Raederle's father Mathom had Second Sight and knew who would win the game before he made the challenge -- or at least knew the winner was also the man Raederle would love; the challenge was really to shield her from being nagged into marrying anyone else.)
 * This is all backstory, mind you. And Morgon, the prince, gets kidnapped before he can 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 Bruce Coville'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 Sweet Polly Oliver and sets off to slay it herself.
 * The basis of the romance subplot in The Edge 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.
 * In the Magic: The Gathering 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. Gadgeteer Genius 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 Chaste Hero and a borderline 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 "Post Modern 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 Huge Schoolgirl), and the only guy who qualified was a 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 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 neither as tall nor as strong as she is (she doesn't care, but her parents might, considering their criteria).
 * 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 Tales of the Five Hundred Kingdoms, 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 Genre Savvy 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 Codex Alera 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.
 * This trope forms the backbone of How Culhwch Won Olwen, one of the oldest surviving works of Welsh literature. Culhwch is cursed by his Wicked Stepmother that he can marry no-one but the daughter of Ysbaddaden the Giant. Ysbaddaden claims that he cannot prepare for the ceremony until Culhwch hunts the giant boar Twrch Trwyth and retreives a 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 certain hero and held by another... the job ultimately involves over forty different tasks and the aid of no less than King Arthur and his warband.
 * And then, once they've done all that, Ysbaddeden's nephew Goreu beheads the giant before the marriage in vengeance for the deaths of his brothers.
 * In another Fractured Fairy Tale, 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
 * The Bible naturally enough has at least one case of this, with David having to bring Saul back 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.
 * 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 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:


 * The Book of Tobit (not to be found in Protestant Bibles) features a woman cursed with a demon so that 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  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 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.
 * Subverted in Ethshar 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 Doctor Who Expanded Universe short story "The Trials of Tara", a pastiche of Shakespearian tropes, has Queen Strella of Tara set tasks for her suitors to avoid marrying any of them, since she believes that King Reynart is still alive.
 * Played with in the Xanth series by Piers Anthony. Magician Humphrey is the setting's resident curmungeonly loremaster, widely known for demanding a years' servitude from people before he consents to use his oracular powers to answer a question for them. When the Gorgon falls in love with him and asks Magician Humphrey to marry her, he actually demands that she serve out the full year of servitude (as his housekeeper) before answering her question. When confronted on this by an understandably aghast cast member, Humphrey quite reasonably points out that at the time she'd asked him to marry her the Gorgon had only just met him and fallen for him after a whirlwind romance, and that it was actually kinder on his part to give her a year's worth of opportunity to actually get to know him and decide if she really wanted to spend the rest of her life living with him and maintaining his household before she was actually committed to doing so, there being no divorce in Xanth.

Live Action TV

 * Monty Python's Flying Circus. In a spoof of this, 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 of course causes the rejected prince to get an evil witch to curse everyone in revenge.

Mythology

 * Greek Mythology 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). Hippomenes (or Melanion) won her by throwing golden apples (kindly donated by Aphrodite) at her feet during the race, which she stopped to pick up. Older Than Feudalism.
 * Standard practice in ancient India, so of course it shows up in the 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 The Hero while Karna becomes The Dragon.
 * In the 19th-century Finnish epic The Kalevala, Evil Matriarch Louhi of Pohjola likes to give her daughters' potential suitors nigh-impossible tasks.
 * One of the points where Germanic and Russian heroic legend meet in Thidrekssaga is when Hartnit (or Ortnit), who ruled in Novgorod (Holmgard) and supposedly son of the hero Ilya Muromets, won a Valkyries 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 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 "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.

Tabletop Games

 * In the Magic: The Gathering 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. Urza completes the challenge by building an automaton with enough power to lift the statue.

Theatre

 * Gender-flipped in Once Upon a Mattress: 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 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 Richard Wagner, Walther must win the Nuremberg's Got Talent time-honored singing contest before he gets the hand of Eva.
 * In the song "Princess of Pure Delight" from Lady in the Dark, a King demands his daughter's suitors answer the riddle, "What word of five letters is always spelled wrong?"
 * The Merchant of Venice: 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 Pericles, Prince of Tyre: 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 incestuous relationship with his daughter", those who answer it correctly will also die.

Video Games

 * In 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
 * In Dragon Quest IV, 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. Considering how clearly she could make her disagreement with that idea known, it's no surprise he backs off.
 * Speaking of Dragon Quest, Dragon Quest V 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 Bianca if you so desire and still get the shield.
 * In the DS Remake, you can marry Debora, but no matter what, you'll always get the Zenithian Shield.
 * Variation in Odin Sphere. 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 fallen in love at first sight with her earlier, he decided to accept the task, though not without being skeptical at first.
 * Maple Story treats this like a quest. And like any quest in Maple Story, requires you to collect Twenty Bear Asses 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 (unstated in the game) backstory of Emperor Mateus Palamecia says he once did this with his daughter, anyone who can reach her at the top of a tower filled with dangerous monsters would have her hand in marraige, 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 is implied to have sparked the insanity that lead The Emperor to try and conquer the world.

Web Comics

 * In Sinfest, Monique will upgrade Slick not to a fiancee or even boyfriend, but a "good friend" if he defeats the Devil, creates world peace, feeds the hungry and treats her like a princess. Slick observes that the Devil offers a better deal.
 * The often NSFW oglaf has this trope as part of this story

Western Animation
"King: Well, since no one's ever come back from the first task, I've forgotten the other two."
 * Buzz Lightyear of Star Command has the characters invoke this when Mira is suddenly reminded of her arranged marriage. Her suitor is challenged to join the Space Rangers and prove himself- cut to the suitor being adorned with medals by the Space Ranger commander for all his offscreen brave and outstanding acts.
 * The He-Man and the Masters of the Universe 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 Rocky and Bullwinkle's 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.

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 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. My, oh my.