You consider me the young apprenticeSituation 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 impossible to please everyone. When the trope is played for laughs, Hilarity Ensues 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 Butt Monkey unwittingly runs into another problem (e.g. jumping into water to avoid a swarm of angry bees, only to fail to see the DANGER: PIRANHA sign behind the bushes until too late). The Two-Timer Date, 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. Wake Up, Go to School, Save the World 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 Greek Mythology which trapped sailors between them, making it Older Than Feudalism. Scylla was a Shape Shifter Mashup 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 B.C.—incidentally around the same time modern historians believe Homer lived). Often dumbed down to "a rock and a hard place". (In fact, the phrase probably had its origins in the aforementioned myth.) Compare Morton's Fork, where a character is presented a Sadistic Choice where every outcome is negative, and doesn't even have the option of trying to stay on the fence.
Caught between the Scylla and Charybdis
Hypnotized by you if I should linger
Staring at the ring around your finger
Caught between the Scylla and Charybdis
Hypnotized by you if I should linger
Staring at the ring around your finger
— The Police, "Wrapped Around Your Finger"
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- Many Love Dodecahedrons 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 Ranma ½ and Tenchi of Tenchi Muyo! are extreme examples.
- In Tokyo Mew Mew, 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 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.
- In All You Need Is Love Naomi relates how it SUCKS being stuck between L and Kira's warring egos; worrying what would happen to her son if they were to discover that 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.
- Liara in the Mass Effect/Sword of the Stars Fusion Fic Shepherd Of The Stars is faced with one of these, forced to chose between preserving an ancient Morrigi temple revealing the true fate of the Protheans or destroying it to save a ship full of innocent people from its now-active defenses. She elects to save the ship, at the cost of the data and much of her scientific credibility.
- Used at the climax of Mrs. Doubtfire, 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...
- Twentyseven Dresses has a bit of a variation, with the main character going to two weddings at once.
- The Jazz Singer 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.
- In Rafael Sabatini'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.
- A Song of Ice and Fire:
- 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 Enemy Mine with the wildings he's supposed to be fighting into outright aiding them because what's coming is even worse. Some of his brothers, however, disagree and object. Vigorously.
- In Ghost Story from The Dresden Files, 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 Exact Words with a healthy dose of From a Certain Point of View.
- Burn Notice 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 Two-Timer Date version.
- Everybody Loves Raymond:
- 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 they both wanted complete and exclusive control over Ray.
- At one point, Debra runs for president of the Parent-Teacher Association at their kids' school opposite 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).
- 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.
- Game of Thrones: The simultaneous wildling attacks in "The Watchers on the Wall" force Ser Alliser Thorne to choose between leaving the Wall or the castle itself in the hands of a lesser commander.
- Prison Break: 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.
- White Collar 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.
- As mentioned above for Greek mythology, in The Odyssey, 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.
- Damn near every single RPG ever made involves this at some point. This trope is especially abundant in Bioware titles.
- The 2010 version of Medal of Honor: Rabbit and Mother have to choose between a gunfight against a huge number of enemies or leaping off a high cliff. Bones heal.
- Resident Evil: Nemesis had the Quick Time Event precursors to the reviled Press X to Not Die mechanic in the later games. You'd often be given two very poor choices like either jump off the bridge or Punch Nemesis in the face, though sometimes doing nothing would be a distinctly third (but usually much worse) option.
- The final trial of Super Danganronpa 2 was constructed by the Big Bad to be like this. The heroes can either leave the simulation as they are while damning the world to be overrun with Junko-infested corpses, go back to reality where their minds and bodies have already been destroyed by Junko while losing all their memories of the battles they fought and relationships they formed inside the simulation, or they can stay in the simulation and trap the 3 members of the Future Foundation who came to rescue them inside as well with Junko (who hates the 3 of them with a passion) in control forever. By the end of it, the protagonist refuses to make a decision.
- A recurring theme in Misfile is Ash trying to balance her happiness against his desire not to lose his/her masculinity.
- Tales from the Pit's R&D Rule #8: You Can't Win. When Mark designs 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 Rares.