Nightfall Series: Sissi to Myra: “You mean to tell me you regret these past two months? You wish you had never been captured and none of this had happened to you?”
In A Brother's Price, there is a practice in Queensland which Princess Ren hates — the small children of treasonous families are killed along with them. Her harsher and more pragmatic sister Halley reminds her that no relatives will take a traitor child, and if they do, well...
Lois McMaster Bujold's A Civil Campaign: "Why didn't you say 'no'?" Miles makes a horribly clumsy public proposal to Ekaterin, who storms out in a rage (for complicated reasons). Later, when Ekaterin is discussing the incident with her aunt, her aunt notes that running off was Ekaterin's way of avoiding the question, and that she could have said no.
Ekaterin: It wouldn't have been polite. The Professora: You could have said 'no thank you'.
For Artemis Fowl, it's: "Artemis... Isn't that a girl's name?" Artemis later gives his answer with a code phrase that sets the final part of an Awesome Moment plan in action.
Jaime Lannister says he wants to die after losing his sword hand, and is asked "Are you so craven?" While he has been called dishonourable or treacherous countless times in the past, nobody has ever accused him of cowardice, and so the question shocks him out of a downwards spiral, and restores his determination to survive and get revenge.
Euron Crow's Eye has proposed a risky plan and tries to sway the doubters. After this, Euron responds with a threat, never actually answers the question, and has changed his plans within hours.
Euron: Have you forgotten? I have sailed the Smoking Sea and seen Valyria.
Rodrik Harlaw: Have you?
In the first novel, Varys uses a pair of these — one answer, and one question — to get under Eddard Stark's armour. When Ned asks him who he serves in the Gambit Pileup, Varys answers "The realm, my lord. Someone must.", and then, when Ned says he's perfectly comfortable dying if it means not giving a false confession, Varys asks him what will happen to his family. This convinces Ned to 'confess' to prevent civil war and save his daughters.
In Angela Carter's "A Very, Very Great Lady and Her Son at Home," the lady of the title recounts her mother's advice to overcome her shyness by imagining the people who intimidate her looking ridiculous on the toilet. Her son, who has been attending to her for most of the story, proceeds to ask "And do you look pathetic on the lavatory, mother?" She promptly collapses.
In the third book in Jonathan Stroud's The Bartimaeus Trilogy, Kitty asks Bartimaeus a single question. "What about you and Ptolemy? The question gets to him so badly that we don't see his reaction until the next chapter, where about half of it deals with him absolutely breaking down and scaring the crap out of Kitty.
Blade of Tyshalle ("What do you want?") The opening quote is about two-thirds of the way through a dressing down Tommie gives Deliann, which takes a little under a page and a half. "What do you want?" happens to be both the identifying code phrase and the central tenet of the persecuted philosophy Tommie holds. Tommie has to ask the question, with mildly different phrasing, over five times. No, Deliann, not what you feel guilty about, not what you think went wrong in the past, not what you like or wish or would settle for. What you want.
A couple of examples from The Belgariad—Garion has a dream the night before his Awesome Moment of Crowning where everyone asks him "Are you ready?" until he accepts that yes, he's ready to take up his birthright.
A sort of inversion of this is that all throughout the series, he keeps asking "Why me?" His aunt finally returns the question, "Would you trust anyone else to do it right?" To which Garion is forced to reply that no; he wouldn't really, therefore burying this question forever.
The Bible: God really likes these kinds of questions (the most frequent one being "What is it you have done?"). This often overlaps with What the Hell, Hero?.
The Bronze Bow, a historical novel, has this conversation between Jesus and Daniel, a man whose hatred of the Romans has grown so all-consuming as to poison his familial relationships:
Jesus: Would you kill for God? Daniel: Yes, of course I would! Jesus: But would you love for God?
Catch-22 has Yossarian ask the show-stopping question: "Where are the Snowdens of yesteryear?" (It's eventually revealed that Snowden had died horrifically during a bombing run, waking Yossarian up to the Crapsack World around him and causing him to realize that he really, really didn't want to die, not for anything.)
Gordon R. Dickson's Tactics of Mistake: Founding Father of the Dorsai, Cletus Grahame, has forced Melissa Khan to marry him as part of his overarching strategy as he explains exhaustively in their bedroom on their wedding night. Melissa has only one question; "Then you never loved me?" "Did I ever say I did?" Cletus responds, and leaves the room. This tells Melissa all she needs to know. He loves her. If the answer was "No", he would have come right out and said "No" instead of evading the question.
Lampshaded (naturally) in the Discworld novels. The philosopher Ly Tin Wheedle was asked "Why are you here?" by a fellow guest at a dinner party (because Ly Tin Wheedle wasn't invited), and took three years to formulate a suitable reply.
Or Wen the Eternally Surprised who, after reaching enlightenment, told his apprentice to ask him a question, anything. His apprentice, who was quite stupid and not at all inclined to be philosophical (...or was he?), just said "Er... what [do you] want for breakfast?" "Ah, one of the difficult ones."
Also parodied with Detritus' interrogation technique, which simply consists of asking the same three questions ("Did you do it?", "Are you sure it wasn't you what done it?" and "It was you what done it, wasn't it?") over and over again for hours until he gets the right answer: "Yes! It was me! I did it! I did it! Now please tell me what it was I did!"
In Jingo, Nobby, of all people, asks some questions that puncture the anti-Klatchian rhetoric going around Ankh-Morpork.
Nobby is actually quite good at these. He'll let Colon go on a rant, seemingly agreeing with everything he's saying, then bring up one of the things Colon said earlier that pokes a great big hole in his logic.
In Monstrous Regiment, after a cease-fire is called, Polly Perks ends up negotiating with one Samuel Vimes about possible war aid to the starving country of Borogravia. When Polly remarks that Borogravia is "a proud country", Sam retorts by asking what Borogravia has to be proud of. Polly is mad at Vimes for asking the question, but she's even angrier at herself for not having an answer, and at her own country for all the centuries of pointless warfare caused by the same thoughtless "proud of being proud" mindset she caught herself falling into.
In Snuff, Vimes shakes the Gordon sisters out of their passive-young-flower-awaiting-a-good-match rut by asking them what, precisely, they actually do.
In The Dresden Files book Small Favor, Michael asks the question "Where is your blasting rod?" to Harry, because Queen Mab of the Winter Court stole it without Harry noticing earlier in the book, and then put Harry's mind into a brainlock that kept him from remembering either his blasting rod or the ability to use fire magic. Harry himself never realized this had happened, and the question sends him into a brief but intense spasming fit once he realizes what had been done to his mind.
In Fahrenheit 451, Clarisse causes Guy to begin questioning his entire way of living by asking the simple question "Are you happy?" and causing him to realize that no, he isn't. He's unable to automatically smile after that as "she had run off with it and he couldn't just knock on her door and ask for it back."
In Fated by Benedict Jacka (the first book of the Alex Verus series) a ghost asks Alex why he didn't run away and hide from more powerful wizards when he could have. Alex gives evasive answers but under repeated questioning admits he stayed to protect another person. It was a revelatory moment for Alex, as he had spent the last few years only looking out for himself.
In The First Fifteen Lives Of Harry August by Claire North, Harry is asked in his third life by Franklin Phearson "What is the point of you?" when he is both unwilling and unable to help him. The question sticks with him and tortures him for all of his lives after, eventually leading to his eventual betrayal of Vincent and systematic destruction of Vincent and the quantum mirror.
The original Fisher King could only be healed by being asked the right question. In some tellings, this is explicitly an Armor-Piercing Question that jolts him out of his self-centeredness; in others it just has unexplained magical properties.
In John C. Wright's The Golden Transcedence, Diomedes cites the Silver-Gray cultivation of such questions — such as, if a philosopher tells you it's right to lie, why do you not suspect him of lying when he says it? Loading such questions into the gadfly virus proves crucial.
In Good Omens, as Adam Young starts to be overtaken by his demonic heritage, his rambles about his plans to kill off all the grown-ups who've messed up the world and leave things to him and his circle of friends, which includes him divvying up the world among them. One of his friends, Pepper, asks what part of the world Adam wants, and Adam slowly starts to come back to normal as he realizes all he really wants is his hometown of Tadfield.
Attempted by Ford Prefect in The Hitchhiker's Guide to the Galaxy, when he asks the young Vogon guard if he actually enjoys his work. Subverted because the guard is too close-minded and stupid to do more than ponder the question for a minute or two, then resume throwing the stowaways off the ship.
To Kill a Mockingbird: In chapter 15, a group of men ready to lynch Tom is stopped dead by Scout when she asks one of them how his entailment (i.e.: an inheritance problem) is coming along. In this case, it's not specifically the question that's armor-piercing so much is that it's coming from the innocent young daughter of Tom's defense lawyer — it breaks the men out of their mob mentality and they quickly disperse in embarrassment, much to the confusion of Scout, who was only trying to make small talk.
In the StarCraft novel, Liberty's Crusade, a reporter confronts Colonel Duke with a Fridge Logic question that probably works on many players — if the Protoss just appeared and started attacking with no warning or communication, how do we know their name?
"Where did we get the name 'Protoss', Colonel? Is that ours, or theirs? And if it's their name for themselves, how come we know it?"
In the Warcraft Expanded Universe short story Of Blood and Honor, Eitrigg tells Tirion that the orcs were an honorable people who were corrupted by the warlocks. Tirion asks why the orcs would go along with the atrocities of the Old Horde if they were honorable. Eitrigg responds with the following question, and later points out that Tirion, who is a wealthy noble in addition to a paladin, has never had to sacrifice anything to do the right thing.
Eitrigg: Have you ever stood against the will of an entire nation, human? Have you ever questioned an order, knowing that to disobey meant immediate death?
In Stanley Ellin's short story “The Question,” the narrator is what he refers to as an “electrocutioner” – the man who rigs up the electric chair and throws the switch on condemned prisoners. It's a secretive job (virtually no one knows the narrator does what he does, including his son), but he's proud that he performs it well. He spends the story telling the reader of how he attempted to persuade his son to follow in his footsteps, citing society's need for the death penalty, comparing rapists and murderers to rabid dogs, and justifying his position as “electrocutioner” by saying that someone must take the responsibility for doing a job no one else wants. His son is shocked and utterly refuses to do it, and reacts with horror when his father says, “It's just a job.” The son asks, Just a job? But you enjoy it, don't you?” As the narrator searches his soul, he reflects on all the men he's watched die gruesomely in his electric chair, and ends the story with the question, “My God, how could anyone not enjoy it?”
Narrator:Does it make you feel big, to make a little boy cry?
In Tim Powers' On Stranger Tides, a captive pirate decides he'd rather be shot than hanged, so asks one of these ("Is it true what Panda Beecher once told me about you?") of the Navy captain who's questioning him. As Panda Beecher is a criminal who pays Navy officers to smuggle goods, on the one hand, and the owner of a whorehouse catering to "exotic" tastes, on the other, the question pushes the captain's Berserk Button and a fight breaks out. Bonus points because it's an Armor Piercing Shot In The Dark: the pirate actually knows nothing against the captain, he just knows lots of Navy officers do business with Beecher.
Suspicion by Swiss author Friedrich Dürrenmatt: Dr. Emmenberger keeps asking Inspector Bärlach what it is that he believes in. When Bärlach refuses to answer, Emmenberger even makes suggestions: Christianity, justice or maybe the law? Bärlach remains silent, forcing Emmenberger to go away in disgust.
In the Star TrekNovel Verse, we have "Are you Whole?" for the Andorians. Supposedly asked of the mythical hero Thirishar by all-powerful Uzaveh (AKA Andorian God), the question drives the modern Andorian culture in its entirety. To be truly Whole requires both reassembling in unity the four genders derived from Thirishar (essentially, bonding with three others in an marriage quad) and gaining knowledge of the "missing piece", an elusive aspect of racial knowledge hidden to the Andorian people. See the Star Trek: Deep Space Nine Relaunch in particular.
It's not actually a question, but it does fit. In the Star Wars Expanded Universe, Padme's Body Guard Crush, Captain Typho, searching for her murderer then finding him and getting utterly curbstomped, manages to stop Darth Vader cold by telling him "I know you killed Padme." He still gets killed after the pause, but he's comforted by the knowledge that he hurt the Dark Lord. Though, not knowing the actual events, he never knows why — his investigation basically went: Padme was killed with the Force, Skywalker was supposed to be bodyguarding her, Skywalker was killed shortly before her, Vader appeared after that, therefore Vader killed them both.
When Zedd is describing Seekers in Wizard's First Rule, he references this trope, saying that a truly great Seeker could bring even a king to his knees by asking a question.
Used in The Tale of Despereaux. The question in, well, question is "What do you want, Miggery Sow?" This comes as such a shock to Mig, who'd never been genuinely asked, that Pea only had to ask once.
In the fifth Temeraire book, Victory of Eagles, Napoleon has invaded Britain. Laurence, who technically committed treason at the end of the last book by saving the dragons of Europe from biological genocide, is given a stay of execution because the Admiralty needs someone to ferret out pockets of French troops — and he has orders to take no prisoners. It's dirty, dishonorable, and depressing, but he obeys until Tharkay arrives, sees his plans for the next attack, and plainly asks, "What are you doing?" It prompts a small breakdown from Laurence, and a frank assessment of what he is prepared to take responsibility for.
The sequel to Those That Wake has this near the end, which opens Laura up to talking about her problems and memory loss.
The Librarian: Tell me, Laura, what is your life like now?
"Do you really want to be remembered as another Garrosh? Another Arthas?"
In the novel Vol'jin: Shadows of the Horde, when Vol'jin plans on going out in a blizzard to rescue Tyrathan, despite the fact that, due to being a Jungle Troll unsuited to snow and still recovering, he has practically no chance of survival, much less success. Taran Zhu asks him this question regarding his motives for the search that gets him to call it off.
"Is it to save the man that you wish to act, or to preserve your own self-conception as a hero? I expect much dusting to be done before you have reached the truth."
In James Garfield's novel Follow My Leader, Jimmy wants revenge against his former friend Mike, who had accidentally blinded him with a firecracker. Jimmy's roommate at The Seeing Eye asks this question: "How would you like to go through the rest of your life knowing you made someone else go blind?"
A more-literal-than-usual example in the children's picture book Exclamation Mark: one of its characters is a literal question mark who barrages the protagonist, an exclamation mark, with a number of curious questions about who he is. The exclamation mark, who has been suffering a crisis of identity about not being like the periods he hangs out with, finally yells "STOP!" in response to the endless questions — and in doing so, realizes just what his identity as an exclamation mark means.
In MARZENA we have Livia, a psychotherapist, asking Lauren, an ex-medical resident, the following question: "So you spent all your time chasing money, but ended up at the age of 25 with no money, no valid professional license, and 100,000 Credits in debt, how do you make sense of that?"
The Riddle Master Trilogy: Not quite a question, but at the end of Heir of Sea and Firewhen Morgon is about to kill Deth, Deth says, "They were promised a man of peace," referring to the words of the Earth-Masters' children, who had given Morgon the sword he was currently holding above Deth's head. Morgon is so affected that he drops the sword and lets Deth walk out of the room intact.
In Wolf Hall, Thomas More remains silent rather than take the oath confirming Henry VIII as head of the Church of England and says that there's no need for his imprisonment; he thinks none harm and does none harm. Cromwell's reply: "What about Bilney? What about Bainham?", two friends of his whom More had burned at the stake for distributing the Bible in English, and says that More ought to be grateful they're sparing him the methods he used on others.
At the end of The Dagger and the Coin series, Clara Kalliam is restored to the barony of Osterling Fells for her heroic actions in overthrowing Geder and the spider priests, thereby saving Imperial Antea and the world, meaning that Clara will once again be a leading member of the Antean royal court. She resolves that she must send her young lover, Vincen Coe, away, since it would be too much of a scandal were it found out that she is carrying on her affair with a servant young enough to be her son. In breaking the news to him, she explains that, if it were just her own reputation at stake, she would not care, but that the problem is that her infant granddaughter has been named after her, and the scandal will damage her reputation as well. Vincen assures her that he will leave without any fuss, but asks her one simple question first: "why do you want your granddaughter to live her life with less courage than yours?" She is completely unable to answer, and then, after a prolonged flustered silence, decides that she will continue her affair with him after all.
In The Reader (2016), Captain Cat asks of Captain Reed, who insists on continuing his journey to the edge of the world to be remembered for all time, "who will remember your crew?" It's harsh because writing doesn't exist in this world, and most people realize that any supporting characters in Reed's legends will be reduced and forgotten over time as the oral tradition degrades.
The Spirit Thief: Banage attempts this when he asks Sara what if it was her son she was mistreating the way she does (sentient, humanlike) spirits. Unfortunately, she's too far gone to care at this point.