Scylla and Charybdis

"You consider me the young apprentice 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"

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 Shapeshifter Mashup that ate sailors, and Charybdis a whirlpool that swallowed ships.

Often dumbed down to "a rock and a hard place". See also Morton's Fork for the conundrums more like "Scylla or another head of the same Scylla".

Anime and Manga

 * 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.

Fan Works
"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: Why do you work for these people?"
 * 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:

Film

 * 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...
 * 27 Dresses has a bit of a variation, with the main character going to two weddings at once.

Literature
"Either option seemed cursed with failure. Macaroth simply had to decide which one to risk. Famously, he showed one of his generals two identical cups of wine and asked him to pick one. “One is elixir, one is poison,” he said. “How can I tell them apart?” the general asked. “By taking one up and tasting it,” replied the Warmaster.""
 * Although not following the trope, 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.
 * Sabbat Martyr has Warmaster Macaroth facing an old military dilemma: if his forces stay overstretched, they are vulnerable to a flank attack, and if he protects the flanks and communications at the cost of weakening pressure on the active front, the enemy may regroup and counterattack.

Live Action TV

 * 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 wife, Debra, and his family—especially his overbearing mother—on an almost episodic basis.
 * Another Raymond example: At one point, Debra runs for president of the neighborhood co-op opposite long-time arch-rival Parker. Although Raymond loves Debra and hates Parker, he realizes that Parker would make a better president.

Mythology

 * 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.

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 Medal of Honor:  have to choose between a gunfight against a huge number of enemies or leaping off a high cliff.

Web Comics

 * A recurring theme in Misfile is Ash trying to balance her happiness against her desire not to lose 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.

Web Original

 * More literally, here, Soren Bowie of Cracked.com does a pastiche of the Internet as The Odyssey. TV Tropes acts as Charybdis, and YouTube as Scylla.