->''You consider me the young apprentice\\
Caught between the [[TropeNamer Scylla and Charybdis]]\\
Hypnotized by you if I should linger\\
Staring at the ring around your finger''
--> -- ThePolice, "Wrapped Around Your Finger"

Situation in which a character must attempt to balance or choose between two (sometimes more) mutually exclusive obligations, desires, ideals, etc.; failure on either front would be disastrous, but it's equally [[FailureIsTheOnlyOption impossible to please everyone]]. When the trope is played for laughs, HilarityEnsues as the character attempts to mollify everyone while the scheme inevitably unravels around him; it's typically subverted when the consequences of failure are revealed to be not so dire as originally believed. Often seen on chase-style cartoons where, by avoiding one foe or obstacle to a good meal, the ButtMonkey unwittingly runs into another problem (e.g. jumping into water to avoid a swarm of angry bees, only to fail to see the [[PiranhaProblem DANGER: PIRANHA]] sign behind the bushes until too late).

The TwoTimerDate, wherein one person must shuttle between two simultaneous appointments, can be a specific example. Note, however, that a Scylla and Charybdis situation may not necessarily be caused by the character's own scheming, oversight or negligence. The outstanding feature of this trope is that the central character must try to appease everyone at once, but cannot.

WakeUpGoToSchoolSaveTheWorld generally results from this, as someone trying to balance a fantastic life with a mundane one realizes the intense pressure from either side.

The trope name refers to the two sea monsters of GreekMythology which trapped sailors between them, making it OlderThanFeudalism. Scylla was a ShapeShifterMashup that ate sailors, and Charybdis a whirlpool that swallowed ships. It has since been rationalized that the "monsters" were a real and dangerous shoal and a real but pretty weak whirlpool in the Strait of Messina, between the Italian mainland and Sicily (both long known to the Greeks and colonized by them by the 8th century BCE--incidentally around the same time modern historians believe Creator/{{Homer}} lived).

Often dumbed down to "a rock and a hard place". (In fact, the phrase likely had its origins in the aforementioned myth.)

Compare MortonsFork, where a character is presented a SadisticChoice where every outcome is negative, and doesn't even have the option of trying to stay on the fence.
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!!Examples:

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[[folder:Anime/Manga]]
* Many {{Love Dodecahedron}}s fall into this trope, with the poor fellow in the center doomed to infuriate (potentially violently) whomever he rejects if he makes a decision. Ranma of ''Manga/RanmaOneHalf'' and Tenchi of ''Anime/TenchiMuyo'' are extreme examples.
* In ''Manga/TokyoMewMew'', Ichigo is trapped in a battle with a monster and desperately trying to finish up so that she can go on a date. In the end, the battle escalates so far that she misses the concert and appears, hours late and in tears. Of course, her boyfriend was nice enough to wait all that time in the rain.
* In ''LightNovel/{{Corsair}}'', Canale, a very young assassin, is planted in the court of Pisare to kill the attorney-general, Sesaam, in exchange for being set free. He falls in love with Sesaam and ends up with the options of either killing the man he loves or revealing that he is an assassin and be cast out or possibly killed by Sesaam, while knowing the assassins guild would just come after Sesaam again anyways and succeed next time. He decides to kill Sesaam and die with him as penance. This doesn't work out as planned.
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[[folder:Fan Fiction]]
* In ''FanFic/AllYouNeedIsLove'' [[Manga/DeathNote Naomi relates how it SUCKS being stuck between L and Kira's warring egos]]; worrying what would happen to [[OriginalCharacter her son]] if they were to discover that [[IKnowYouKnowIKnow he knows what they know]]:
--> '''Naomi''': You do realize that if L or Kira were to find out they would kill you... If Light finds out he'll probably kill you. However he might keep you around as a pawn and use you to reach his ultimate goal of creating a cult civilization in which he's god. That means that if you don't find yourself drowning in a swimming pool you'll find yourself brainwashed and tortured and then thinking nothing at all... If L finds you that's a whole different story. L won't kill you but he will tie you to a chair and leave you there to rot for fifty days and then pretend to execute you only to leave you alive so that the government can perform nasty experiments on you. He probably won't give you a trial but instead will leave you in a mental institution or have you killed off by thugs. Then he'll steal your name and use it as yet another detective name and that will be the end of that.
--> '''Duck''': [[OnlySaneMan Why do you work for these people?]]
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[[folder:Film]]
* Used at the climax of ''Film/MrsDoubtfire'', where Daniel shuttles between a dinner with his boss and dinner with his family, changing in and out of his Mrs. Doubtfire makeup with each transition. Of course, on top of that, he's been drinking...
* ''[[TwentysevenDresses 27 Dresses]]'' has a bit of a variation, with the main character going to two weddings at once.
* ''Film/TheJazzSinger'' has Jack/Jakie have to decide to either star in a Broadway show on opening night or fill in for his dying Cantor father and sing Kol Nidre for the Yom Kippur Service. The producer warns him that if he misses the show, his career may be ruined, but he wants to be there for his family. He decides to fill in for his father and miss the show, and his father forgives him before dying.
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[[folder:Literature]]
* In Creator/RafaelSabatini's ''The Hounds of God'', Lady Margaret described herself as escaping Scylla, but being sucked into the whirlpool of Charybdis. This refers to her technically being rescued from being kidnapped, but only to be brought to trial for witchcraft. This slightly differs from the main trope, in that the Margaret is simply brought along for the ride rather than being allowed to choose.
* ASongOfIceAndFire has Jaime Lannister, who gets no small amount of grief from the mutually exclusive demands of knighthood and the oaths it brings. You swear to serve and protect the king, defend the people and respect your father. So what do you do when the king is at war with your father and intends to massacre his subjects?
** Jon Snow gets this too. He goes beyond an EnemyMine with the wildings he's supposed to be fighting into outright aiding them because what's coming is [[ZombieApocalypse even worse.]] Some of his brothers, however, disagree and object. [[KnifeFight Vigorously.]]
* In ''Ghost Story'' from TheDresdenFiles, [[TheFairFolk Lea]] strikes a deal with Dresden, and gets caught in the position of having to uphold the deal, which stated that he got answers to three questions. One of those questions was "Who killed me?" Unfortunately for Lea, she also had to uphold a promise to not tell Dresden who killed him. Presumably, this promise was given to Mab. She manages to balance these two conflicting promises by using ExactWords with a healthy dose of FromACertainPointOfView.
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[[folder:Live Action TV]]
* ''Series/BurnNotice'' has a dramatic example when Michael has to choose between helping Anson and hurting the CIA or stopping Anson by telling the CIA about him and suffering his revenge.
* Nearly every SitCom in existence has pulled the TwoTimerDate version.
* ''Series/EverybodyLovesRaymond'':
** Raymond found himself in the middle of conflicts between his violent and immature wife, Debra, and his family--especially his overbearing and guilt-mongering mother--on an almost episodic basis. He was pretty much in a situation where there was no way he could please one without royally pissing off the other due to the fact that [[NotSoDifferent they both wanted complete and exclusive control over Ray.]]
** Another ''Raymond'' example: At one point, Debra runs for president of the Parent-Teacher Association at their kids' school opposite [[SitcomArchNemesis long-time arch-rival]] Parker. Although Raymond loves Debra and hates Parker, he realizes that Parker would make a better president (Debra reacts by stomping on everyone's jackets--crushing Robert's cell phone in the process--and rather ridiculously comparing Ray to antebellum slaveholders).
* ''Series/{{Frasier}}'' Niles is caught between Mel and Daphne when Mel makes Niles pretend they are happily married after he runs off with Daphne. Mel won't give him a quickie divorce otherwise but Daphne almost breaks up with him due to the strain of watching Niles pretend to be in love with Mel.
* ''Series/PrisonBreak'': Towards the end of the show the General and another of Michael's enemies each have one of his loved ones held hostage and they both want Scylla.
* A very much life-and-death example in the 2008 version of ''{{Survivors}}'' where a father attempts to keep his two kids inside their house, fearing any contact with the outside might land them with the virus (which they have not yet come into contact with). The daughter refuses to stay in this existence, though, and escapes, to be shut out by her dad. Eventually it boils down to a choice, posed by two of the main characters who take the daughter temporarily under their wing: either risk leaving the effective imprisonment in their own home and risk exposure to the virus, or stay inside and eventually starve to death when all the food runs out.
* ''Series/WhiteCollar'' has Neal trying to choose between keeping Peter happy and keeping Mozzie happy early in S3. He doesn't want to rat Mozzie out to Peter but he also doesn't want to disappoint Peter by fleeing with the treasure.
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[[folder:Mythology]]
* As mentioned above for Greek mythology, in ''Literature/TheOdyssey'', Odysseus has to choose between passing by Scylla and Charybdis. Both creatures live on opposite sides of a narrow ocean-pass, and he has to pass by one of them to continue. He chooses to pass by Scylla. Scylla snaps up six of his men, killing them, but passing by Charybdis would have caused the entire ship to be swallowed up, killing the entire crew.
** Later on, he is forced to pass by the two monsters ''again'', this time by himself in a raft (long story). This time, he passes by Charybdis. Alone, he's able to grasp onto a fig tree growing on an outcropping near the whirlpool, and is able to recover his raft after it's swallowed, and then expelled.
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[[folder:Video Games]]
* Damn near every single RPG ever made involves this at some point. This trope is especially abundant in Bioware titles.
* The 2010 version of ''MedalOfHonor'': [[spoiler: Rabbit and Mother]] have to choose between a [[BolivianArmyEnding gunfight against a huge number of enemies]] or [[NoEscapeButDown leaping off a high cliff]]. [[spoiler: [[LeapOfFaith Bones]] [[BadassBoast heal.]]]]
* ''[[Franchise/ResidentEvil Resident Evil: Nemesis]]'' had the QuickTimeEvent precursors to the [[ScrappyMechanic reviled]] PressXToNotDie mechanic in the later games. You'd often be given two very poor choices like either jump off the bridge or ''Punch [[ImplacableMan Nemesis]] in the face'', though sometimes doing nothing would be a distinctly third (but usually much worse) option.
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[[folder:Web Comics]]
* A recurring theme in ''Webcomic/{{Misfile}}'' is Ash trying to balance her happiness against his [[GenderBender desire not to lose his/her masculinity]].
* ''Webcomic/TalesFromThePit'''s [[http://tumblr.com/xfd2sgah1t R&D Rule #8: You Can't Win.]] When Mark designs [[PowerEqualsRarity powerful rare cards that see tournament play]], he gets angry emails about how expensive it is to play in tournaments. When the rare and mythic cards are too weak to see tournament play, he gets angry emails complaining about {{Junk Rare}}s.
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[[folder:Web Original]]
* More literally, [[http://www.cracked.com/blog/exploring-internet-in-11-days-epic-online-odyssey/ here]], Soren Bowie of ''Website/{{Cracked}}'' does a pastiche of the Internet as ''Literature/TheOdyssey''. TVTropes acts as [[TVTropesWillRuinYourLife Charybdis]], and Website/YouTube as [[{{Troll}} Scylla]].
* LetsPlay/SomethingAwfulDungeonsAndDragons: Minerelle in regards to the book of Ioun, trapped between her party leader, her evil god, and a dragon lich.
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