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But Not Too Challenging

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Some people hold the idea that an easy victory is unsatisfying, which is why people prefer challenges over a guaranteed win. While some people are genuine in their desire for an actual challenge, for others, their idea of a "challenge" is essentially just a delayed victory; they're more interested in the idea of a challenge rather than an actual challenge. These type of characters try to have their cake and eat it too, by desiring "challenges" that are just hard enough to force them to try, but not so difficult that they can actually fail.
How this trope might manifest depends on the nature of the challenge a person supposedly desires. A pseudo-Blood Knight might claim to desire strong opponents, but in truth just wants an opponent who won't go down right away; when faced with a genuinely challenging opponent, they'll either cower in fear or throw a hissy fit over the possibility of actually being beaten. Someone who's used to easily winning contests might become excited at the idea of having to work for their victory, but throw a tantrum when they actually lose. A normally unstoppable villain might express amusement at the idea of a hero who doesn't immediately lose to them, but will lose it when said hero proves to be an actual threat to them and their plans.
Romantic and sexual conquests are another area in which this trope can apply. A common example involves characters who are easily capable of seducing people falling for a person who doesn't immediately fall for them; while some people might enjoy having to chase and put effort into winning over a crush, some of those same people might become enraged at the idea of someone being genuinely uninterested in them despite their efforts. With a Love Triangle, some people might like the idea of competing for someone's love, but won't take it well if the rival ends up being the winner. A man who hates being chased by women might enjoy going after women that don't show interest or take the initiative, but become bitter when a girl he chases after won't give him a chance.
Sub-Trope of Sore Loser. Compare Be Careful What You Wish For, Wanting Is Better Than Having, and Didn't Think This Through, all of which this trope can overlap with if someone who desires a challenge fails to take into account the possibility of failure. Examples involving romantic/sexual conquests often overlap with Entitled to Have You. Contrast Worthy Opponent and Honor Before Reason, which this trope might subvert.
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Dune: Feyd-Rautha Harkonnen loves to demonstrate his prowess by participating (rigged) gladiator matches where he emerges victorious every time. For his hundredth match on his 17th birthday, he makes it a bit more of a challenge by dueling an elite Atreides soldier. However, when it becomes clear that Feyd overestimated his opponent, he falls back on his failsafes (poison blades and Trigger Phrase activated paralysis) to make sure he still wins.
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Beauty and the Beast (2017): Part of the reason why Gaston is obsessed with Belle because, unlike every other girl who eagerly chases after Gaston, Belle isn't interested in him, which Gaston interprets as Belle Playing Hard to Get. Once Gaston realizes that Belle is genuinely uninterested and not playing coy, he tries to blackmail her into marrying him by holding her father hostage, which shows that while Gaston enjoys the idea of chasing women, he's incapable of accepting the idea of actually being rejected by a woman.
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The Simpsons:
It's a recurring thing with Lisa Simpson, as she is often frustrated with how little intellectual challenges she has in Springfield Elementary School, but any time she has less than straight A's, she doesn't take it well. These episodes often show that while Lisa might seem like a Child Prodigy when she's contrasted against a town full of apathetic idiots like Sprinfield, when placed in a competitive environment with actual standards she's less "gifted" and more "just above average".
In the episode "The Secret War of Lisa Simpson", she enrolls in a Military School alongside Bart (who is not there by choice but comes to thrive in it) because it is more intellectually stimulating, but literally everything else (physical training, firearms training, being hazed by the other students, the borderline Deadly Graduation) is beyond her.
Played for Laughs in "Girls Just Want to Have Sums". Lisa demands a challenge from the boys’ side of the elementary school, only to immediately run into an angry wolf. She (half-annoyed) reiterates she meant a mental challenge, to which the wolf sheepishly wanders away.
In "Waverly Hills, 9-0-2-1-D'oh", Lisa goes to a new school and gets a B+ on her homework instead of an A+ like usual. Not being the resident smart kid makes her realize she doesn't like the new school as much as she expected.
In "Bart Vs. Lisa Vs. The Third Grade", Lisa is sent forward to Third Grade because of her smarts and Bart is punished for his pranking by being sent back to Third Grade. Lisa's grades plummet slightly to plain Asor B-Pluses because the material is harder while Bart, again, thrives because he still remembers the material, including the answer keys to the tests (which have not changed). When Lisa is given the chance to go back to her previous grade and be a Normal Fish in a Tiny Pond, she eagerly takes it.
The episode "King of the Hill" plays with this trope. When Homer Simpson finds out his Sherpa guides have been physically carrying him up the mountain he fires them, but he also disregards their comment that if he's so determined to do it the "right" way, he should backtrack the climbing they've already done and go back up all by himself.
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Dragon Ball:
Saiyans, despite claiming to be a warrior race, are essentially just sadistic bullies whose idea of a "strong opponent" is someone who's just strong enough to not be immediately curb stomped by them, but not strong enough to be an actual threat. Goku is an anomaly among Saiyans for preferring to fight people who can actually defeat him.
Captain Ginyu, during his fight with Goku, actually yells at Jeice for assisting him, stating that he doesn't need his help, implying that Ginyu has a sense of honor despite being evil. When he realizes that Goku is holding back, he lets Goku power up in order to get a better fight out of him. When Goku reveals just how powerful he really is, Ginyu has a minor Freak Out and decides to play dirty by stealing Goku's stronger body for himself, showing that Ginyu's "honor" is disposable if it's inconvenient.
After achieving his perfect form, Cell organizes the Cell Games in hopes of fighting a opponent worthy of his newfound strength, and even gives his enemies a week to prepare for the fight. He maintains a seemingly Affably Evil facade and a show of good sportsmanship in the lead-up to the tournament and during his fight with Goku, but when Super Saiyan 2 Gohan turns out to be vastly stronger than him, he proves to be a Sore Loser and tries to blow himself up and take the whole planet with him.
Super Buu is a Blood Knight who didn't destroy the Earth immediately because he remembers Goku's promise of a challenging opponent for him to fight. He also admits that the (initial) reason he didn't absorb Gohan alongside Gotenks and Piccolo is because he wanted a strong opponent to test his new power on. Of course, it's clear that Super Buu's idea of a Worthy Opponent is someone who doesn't die in a couple of hits, and he actually despises the idea of anyone being his equal in strength or being stronger than him. When he's first outmatched by Gohan, he undergoes a Villainous Breakdown and deliberately self-destructs (knowing he can reconstitute his body) so he can wait one hour before putting his plan to absorb Gotenks and Piccolo in motion. When Vegito starts to get the upper hand on him, Super Buu grows increasingly angry and desperate to win, which allows Vegito to put his own plan into motion by letting Buu absorb him so he can rescue all of the absorbed victims trapped inside Super Buu's body.
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In Castlevania: Lament of Innocence, the vampire Walter Bernhard is so bored with his eternal life that he provokes human warriors to attack his castle by kidnapping their loved ones, even sparing Rinaldo so that the alchemist will arm and assist said warriors. However, the end result of these countless escapades, up until his abduction of Sara and his resulting feud with Leon Belmont, is that the warriors will either die or have to deal with their newly-vampirized loved ones. When Leon manages to actually take him on and wound him with the Vampire Killer, Walter is shocked that he's actually being beaten in fair competition with a mortal human.
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 Castlevania: Lament of Innocence (Video Game)
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Danny Phantom: Stranded: The main reason why Colette is obsessed with stealing Danny from her stepsister Star is because unlike every other guy Colette stole from Star, Danny rebuffs Colette's advances rather than immediately falling for her, which forces Colette to put actual effort into winning over Danny. At the same time, Colette is Not Good with Rejection, as she's willing to resort to actions such as kidnapping, attempted murder, and blackmail to steal Danny or force him to be with her, showing that she's more interested in the idea of a challenge and is ultimately too proud to accept a guy preferring Star over her.
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I Woke Up As a Dungeon, Now What?: Karyn's pride causes her to flip-flop back and forth on whether she wants Taylor to go easy on the party, or all-out anything-short-of-death. She gets upset if she feels she's being coddled, but can't handle the psychological warfare and endless dirty tricks when Taylor is getting serious. Taylor finds her inconsistency annoying.
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Overlord (2012): According to Word of God, Zesshi Zetsumei (real name: Antilene Heran Fouche) is the World's Strongest Woman before Ainz and the Great Tomb of Nazarick are transported to the New World; she is the only person serving a nation who goes over level 50, being in the high 80s in a place where a legendary creature is equal to level 30 and an average human adventurer is likely to be less. Unsurprisingly, Zesshi is bored early on in the series as there's nobody, besides the Platinum Dragon Lord, who could challenge her and wishes for a Worthy Opponent to defeat her in combat and bear his child. Ironically, when she does get her wish upon engaging Mare, a Level 100 Dark Elf, for the first time in Volume 16, she doesn't enjoy herself nor feel attracted to Mare at all because 1) Mare is a child by elf standards, 2) she thought Mare was a girl due to his androgynous looks and swimsuit-like armor, 3) the battle was an ensuing curb-stomp with her suffering on the end with Mare not trying to kill her, and 4) the battle not going as she would expect; an epic battle that would drive both combatants to give every single drop of what they had until the best of them emerged victorious.
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Dragon Ball Z Abridged: Just like in canon, Cell holds the Cell Games to get a good fight from Goku only to get agitated when Goku forfeits in the middle of the fight. He also doesn’t take well to Goku sending out Gohan believing him to not be much of a fight, though he becomes interested in the power Gohan states. When Gohan refuses to let that power out, he becomes pissed again that he decides to just kill everyone which gets Gohan to go all out. This get Cell ecstatic until he sees just how much Gohan overpowers him to the point of dragging the fight to torture him, which gets Cell to have a fit of his own.
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One-Punch Man:
Suiryu claims he wishes to feel the thrill of a real fight, just like Saitama and Boros, but the moment he's faced with a situation where he might actually lose, he immediately loses all composure and flies into a rage. He outright states he doesn't find losing to be fun, which contrasts Boros, who had the time of his life even though he completely lost.
Superalloy Blackluster is revealed to be this during his fight against Garou in the Monster Association arc. He thought he was looking for an opponent that could push him to use 100% of his power, but when he finally fights against Garou and finds himself pushed to that point, he realizes that what he wanted wasn't so much a "good fight", as a fight that could make him feel good about himself. He never considered the possibility that he might actually lose. He was looking for an equal, not a superior. After the Garou arc, he's shown falling victim to his fears of loss no matter how much he trains.
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Sognic: Mall-tiverse of Madness: In episode 3, Roter.exe places each of the six main heroes into personalized "nightmares" and attempts to scare them in various ways. Almost all of them laugh off his attempts to scare them, making Roter.exe increasingly frustrated. The only one who Roter.exe successfully scares is Knockles, who has a Comical Overreaction because Roter.exe replaced his canned pasta with a Shoddy Knockoff Product. Roter.exe remarks that scaring Knockles was so easy that it wasn't even fun.
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Star Trek: Deep Space Nine: In "Rivals," O'Brien and Bashir both regret playing each other at racquetball for this reason. Bashir, having played competitively at the Academy, is the superior player, but O'Brien's pride won't let him either concede, or accept Bashir throwing the game. Bashir eventually fakes a medical emergency to get away (fearing a real medical emergency if O'Brien has a heart attack), but knows he'll insist on a rematch.
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Lord Hong in Interesting Times:
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The Legend of Zelda:
The Legend of Zelda: Spirit Tracks: Byrne has spent an untold number of years training to be the best warrior he can be. When he actually faces defeat at the hands of Link and Zelda, he is completely aghast that he could ever lose, least of all to mere Hylian children.
The Legend of Zelda: Tears of the Kingdom: The Demon King Ganondorf expresses contempt for the world he awakened to, lambasting them as a bunch of peace-loving cowards who made a world too soft for him to face any difficulty or satisfaction in conquering them. Link, the prophesied hero, appears to earn his respect as he proves to be a legitimate challenge in combat for the Demon King. But once Link actually wins their duel, Ganondorf flies into a rage as he cannot stand the thought of being defeated by "a mere mortal". In a fit of spite, the Demon King turns himself into a mindless dragon, just for the sake of finishing Link off and to slaughter all of Hyrule.
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Yu-Gi-Oh! ARC-V: The Greater-Scope Villain Z-ARC is revealed to be the this as the Duel drags on. Despite his Blood Knight and Challenge Seeker tendencies, he quickly feels insulted when Shingeo and Crow accuses him as Dirty Coward whose so scared of losing for his Purposely Overpowered cards. When he actually does lose despite all efforts, he undergoes a huge Villainous Breakdown.
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Death Note: While Light Yagami does enjoy a "battle of wits" against L, and later Near after the 5-year timeskip, he'll never accept losing as a possibility. His refusal to accept loss is justified given that "losing", in his case, means that he can kiss whatever goals he has as Kira, his social life, and his freedom goodbye behind bars, assuming that he doesn't get killed beforehand or get the death penalty. It also shows his raging God complex, narcissism, and refusal to admit to any fault. This attitude is what really separates him from L, as by his own admission, he also doesn't like to lose, but the latter's very self-aware of his flaws.
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The Three Musketeers (2011): The Cardinal mocks Rochefort when he sees him practicing sword-fighting by himself. He makes a tongue-in-cheek observation that the imaginary opponent is always as challenging as one imagines him to be, so as to make victory satisfying, even though victory is guaranteed.
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Mother 3: At one point in The Empire Porky Building, the player has to play three games against Master Mini-Porky, a robotic copy of Porky. In order to progress the player has to lose, but just barely. The reason being is that while Porky is too much of a Sore Loser to accept being beaten, he's also too proud to accept an easy win, meaning that you have to lose by such a small margin that it makes Porky's victory seem more impressive.
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Baki the Grappler: The five death row inmates all escape containment at roughly the same time in order to find a fighter who can make them "experience defeat". Turns out, they do not take losing all that well.
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Son of the Sannin: Madara Uchiha becomes this as part of his Adaptational Jerkass treatment, in stark contrast to canon where Madara can genuinely respect opponents who give him a challenge. Here, while Madara will praise opponents who last more than a few seconds against him, he will start throwing a tantrum when they start getting the upper hand on him. Case in point, one of the most noticeable changes is how he acts towards Maito Gai when the latter opens the Gate of Death: Canon!Madara comes to see Gai as a Worthy Opponent for besting and almost killing him, and his final attempt to kill Gai before he succumbed to the fatal aftereffects was done as an act of mercy from his point of view. Here, Madara actually mocks Gai for using a technique that will kill him, insulting his efforts and laughing after he barely survives Gai's final attack.
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Yu-Gi-Oh!:
Seto Kaiba is an obsessive Duel Monsters player, always trying to improve his skills and often slandering those he perceives as lesser-skilled. When he actually gets outplayed by Yugi, he spends the rest of the series trying to one-up him.
Noah Kaiba actually tries to stop one of his henchmen, Johnson, from cheating during his duel against Joey, as Noah wants to prove his superiority to Seto and his associates by beating him fair and square. During Noah's duel against Seto, the minute the latter starts winning, Noah decides to cheat by using their brother Mokuba as a Human Shield, and after Seto rescues Mokuba, Noah decides to use his power over the Virtual World to turn Seto and Mokuba to stone and declares himself the winner by default. Yugi calls him out for his hypocrisy.
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Power Rangers Zeo: When King Mondo's first monster is defeated by the Rangers, he is initially enthusiastic about facing opponents who can actually put up fight, as every other planet he conquered went down with ease. It doesn't take long before King Mondo starts suffering Villainous Breakdowns from having his plans continuously be thwarted.
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The Legend of Zelda: Spirit Tracks: Byrne has spent an untold number of years training to be the best warrior he can be. When he actually faces defeat at the hands of Link and Zelda, he is completely aghast that he could ever lose, least of all to mere Hylian children.
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Vermintide II: The Chaos Lord Bödvarr Ribspreader makes a big show of bragging that he'll personally cut down all the heroes in his Boss Battle, but starts calling for backup as soon as they put a dent in his health.
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Ars Magica: Apprentice mages in House Tremere need to defeat their master in a formal, non-lethal Wizard Duel to complete their apprenticeship. It's always a serious fight, but it's bad form for the master to go all-out to avoid losing, as they might if the stakes were higher.
 But Not Too Challenging / int_eed321b1
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 But Not Too Challenging / int_f5855286
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But Not Too Challenging
 But Not Too Challenging / int_f5855286
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The Legend of Zelda: Tears of the Kingdom: The Demon King Ganondorf expresses contempt for the world he awakened to, lambasting them as a bunch of peace-loving cowards who made a world too soft for him to face any difficulty or satisfaction in conquering them. Link, the prophesied hero, appears to earn his respect as he proves to be a legitimate challenge in combat for the Demon King. But once Link actually wins their duel, Ganondorf flies into a rage as he cannot stand the thought of being defeated by "a mere mortal". In a fit of spite, the Demon King turns himself into a mindless dragon, just for the sake of finishing Link off and to slaughter all of Hyrule.
 But Not Too Challenging / int_f5855286
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 But Not Too Challenging / int_f5855286
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But Not Too Challenging / int_f5855286

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 But Not Too Challenging
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Character Flaw Index
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Index Backfire
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 I Woke Up As a Dungeon, Now What? (Fanfic)
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