Caught between the Scylla and Charybdis
Hypnotized by you if I should linger
Staring at the ring around your finger"
A 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 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.)
- 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.
- Yu-Gi-Oh! VRAINS: In episode #42, seeing Playmaker continuously fail to perform Storm Access and even getting a forearm ripped off, Ai stepped in and transformed into a larger version of himself to prevent Playmaker from falling. Ai then proceeded to sacrifice a part of himself to repair Playmaker's arm and shield him from the flying debris. He really could have been erased. Even if he could have been erased either by Playmaker losing or being destroyed by the debris and had the slightest chance of surviving by saving Playmaker, he still saved Playmaker from certain death while risking his own life. Ai may have been willing to sacrifice himself because he wanted to make it up to Playmaker for lying about losing his memories.
Ai: "Be quiet! This is how I atone!"
- In Goddess Creation System Button, Jun'er's personal eunuch attendant, acts completely loyal to him while actually answering to his mother the queen. However, after Jun'er starts behaving more seriously and paying more attention to his surroundings he quickly notices his attendants divided loyalties. This puts Button in an extremely dangerous position because either the queen or prince could easily have him executed and he can't possibly satisfy both. But Jun'er is a nice guy, so he just makes it clear he knows and then continues about solidifying his own position.
- 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.
- One canto of The Divine Comedy opens with the protagonist stuck in silence because he can't decide whether to ask how nuns forced to break their vows could justly be given a lower position in Heaven or to ask if those dead nuns really live on the Moon.
- In The Dresden Files: Ghost Story, 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. We eventually find out Harry had himself killed in a vain attempt to cheat Queen Mab out of having a wizard as her Winter Knight.
- 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.
- In Percy Jackson, the Sea of Monsters can only be entered by passing between them and it doesn't matter where you try to enter from cuz they'll always appear in the way.
- 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.
- The Asterisk War: The prize for being on the winning team at a Festa is for the IEFs to grant each team member any boon it is within their power to provide, which, since they basically rule the world, means almost anything that isn't a physical impossibility. Occasionally, however, a winning Genestella's wish puts them into a bind, particularly if it impinges on the IE Fs' political power: if they refuse to grant a wish that might cause them problems, they put the legitimacy of their own regime at risk, so they normally try to negotiate a compromise with the champion.
- Madiath Mesa asked to become an executive at Galaxy, but they didn't want to make an exception in their intake procedures for him (which involve Brainwashing for the Greater Shareholder Value). The solution was to make him an Authority in Name Only, giving him the job of chief administrative officer of the Festas but no other official power in the company.
- Claudia Enfield wishes to interview her Orga Lux's creator Ladislav Bartoik, who was involved in a mysterious incident in the recent backstory and is spending life in prison at a Black Site. Galaxy, the IEF that backs Seidoukan Academy, would suffer significant political harm if whatever happened became public knowledge. They first send Psycho for Hire Gustave Malraux to try and drive her prospective Gryps Festa teammates away from her, then escalate to sending Bujinsai Yabuki's Ninja clan to assassinate her. When that fails, Galaxy agrees to let her meet Bartoik on condition of keeping anything she learns from him secret.
- Politically Active Princess Julis's second wish is to expand the power of Lieseltania's monarchy, in hopes of eventually ending its Puppet State status to the IEFs. In volume 12, the IEFs are mentioned to be negotiating with her and her brother King Jolbert on just how much leash to give him.
- 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.
- 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.
- Star Trek: Picard: In "Absolute Candor", La Sirena and its crew finds itself having to fight off a Romulan Bird-of-Prey while at the same time avoiding crashing against Vashti's planetary shields or getting blown up by the planet's orbital drones.
- 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.
- In some versions of the myth of Jason and the Argonauts, the Argo passes through the strait as well, but rather than choose between one of the monsters, some nymphs, lead by Thetis, appear and carry the Argo out of the strait safely. It helps that the gods liked Jason much more than they did Odysseus.
- 1916 - Der Unbekannte Krieg plays this straight. The protagonist, a lone German soldier, is stuck in a trench infested with carnivorous dinosaurs, and even if he does manage to escape, he'll be stranded in no man's land, completely exposed to the enemy.
- Medal of Honor (2010): 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 3: 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 Danganronpa 2: Goodbye Despair 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 three members of the Future Foundation who came to rescue them inside as well with Junko (who hates the three 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.
- Star vs. the Forces of Evil: Her pursuit of monster equality hasn't been as simple as she wanted it. She discovered that she's part of a line of ancestors who were imposed by the High Commission to keep Eclipsa's monster-Mewman hybrid daughter from the throne. She's now stuck with a very difficult decision. If she maintains her role as Princess then she betrays her ideals, if she allows Meteora to take the throne then she loses her identity as a princess, and Meteora is clearly completely insane and unfit to lead. Fortunately for her, Eclipsa doesn't care about the throne as much as she just wants her daughter back, and after Meteora is magically regressed back into a baby, she wants to give her daughter another chance at growing up.