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Bob has infiltrated the Villain's side, or possibly is undergoing a Heel Face Turn or similar alliance-shifting move. Alice happens to be a prisoner of the Villain. Bob must somehow convey to Alice that he's there, or that he's changed sides, or some other information. However, he can't just go talk to her, because the guards would get suspicious.
Therefore, he makes the guards believe that he wants a few minutes alone with the prisoner, perhaps she needs to be "interrogated" or "taught a lesson". The guards let him into Alice's cell and leave them to it, chortling at the evilness of their buddy's intentions.
Once Bob manages to convince Alice that he was trying to fool the guards, (though maybe only after recovering from a vase to the head she was going to use on the real guard to try to escape) he can finally get that information to her, possibly even help her escape somehow.
Of course, Bob could be the Mad Scientist's Beautiful Daughter or other female henchwoman doing a High Heel Face Turn. If the audience has been unaware of Bob's alignment up to that point, this can be the way the Reverse Mole is revealed. It's also highly likely that Bob/Bridget has been putting in place The Infiltration or acted as the Fake Defector.
Compare Merciful Minion.
- In the 2003 anime version of Fullmetal Alchemist, Edward Elric pulls a hilarious version when trying to contact the fake Elric brothers.
- In Mobile Suit Gundam Unicorn Riddhe visits Audrey's cell twice, first to interrogate her and later to help her escape to Earth with him. Subverted in that the Federation is not the bad guy (we think) and Riddhe wasn't trying to fool the guard (just knocking the guard out instead).
- In the Blake and Mortimer book The Voronov Plot, Blake, posing as a Soviet officer, tries to pull this in order to contact an imprisoned British spy. Unfortunately, he is interrupted by Captain Ilkor...
- This can be subverted if someone sticks around to watch, or if the act must be performed in public. There was a scene from the end of a Snapefic in which a Heroic!Snape was trying to save the kids while pretending he was about to kill them, as part of a celebration held by the Death Eaters. So he's acting all crazy and even forcing Hermione to kiss him (no, no such Ship in this fic) so he could get close enough to hand her a vial of antidote and whisper some instructions.
- More fetish-oriented fics glee at Snape having to completely go through with sexual torture on a captive Hermione/Harry/Whoever because Lucius/Voldemort is watching. Then maybe hand over the tools necessary for escape afterwards, if they can be bothered to continue the rest of the story!
- In Gladiator, when Lucilla arrives at Maximus' cell, she tells him "rich matrons pay well to be pleasured by the bravest champions". He has been chained up in preparation for her visit. In fact she's there to tell him there is a growing conspiracy against Commodus, and to ask him to meet a politician who's involved.
- Pre-arranged in Ocean's Eleven, when the guy sent in to torture Danny Ocean was set up all along by Danny to show up and pretend to torture him so that he could escape.
- Rusty's posing as a federal agent to rescue Basher from the cops, near the beginning of the film, would also qualify, partially subverted by being done in public (although he does send the arresting police officer off on a wild goose chase to talk to Basher alone and free him from handcuffs).
- Textbook example in The Green Zone (but no sexual innuendo), though it turns out the target prisoner is beaten up pretty badly and the conversation doesn't go as planned.
- Xanth, from The Edge Chronicles does this for Magda, when she is captured by the Guardians of Night. Slight variation; instead of pretending to be evil for the guards, he just pulls rank on them.
- Sawyer uses this to talk to Sayid in season 5 of Lost.
- Colonel Mitchell has to pretend to attack (and then pretend to torture) a captured Teal'c so they can plan their escape in an episode of Stargate SG-1.
- On Burn Notice (Mind Games) Michael accidentally exposes an undercover cop while undercover himself. He shoos the others away while he threatens the prisoner, and takes the oppourtunity to mention that he's undercover too and slip the cop a means of escape.
- The sad irony here was that Michael was trying to frame the guy he thought was a Complete Monster as an undercover cop to his crime boss. Realizing he has condemned a good man to death, Michael is determined to make sure the cop lives to go back to his wife and kids.
- All the time on Alias. A particularly good example is Irina in "Passage Pt. 2", having pulled a Batman Gambit and aligned herself with Cuvee (which Sydney and Jack think is a Face Heel Turn). She puts on a good show of interrogating Jack and gets Cuvee to leave her alone with him. She pistol-whips him, but also slips him the key to his cuffs and tells him how to find the nukes they've come to find.
- Subverted in the fourth season of Babylon5: Garibaldi successfully uses this excuse to get past the first set of guards around Captain Sheridan, but the ones directly outside the cell demand to see authorization, so the rescuers just knock them out. Turns out that was actually the plan all along; asking to get inside was just a ploy to make one of the guards think of the door code so that their telepath could pick it out of his mind.
- Played straight in the fifth season, when Londo uses it to break Na'Toth out of the Imperial dungeons.
- Gwen tries this in Merlin during the season 3 finale with Sir Leon as the prisoner. She just claims she has "food for the prisoner" and once she's inside the cell, she tells him that she wants to help him escape. They don't know that the conversation is actually being listened to by the bad guys, so they weren't actually alone...
- George Washington pulled this on a double spy. He had the guards leave him and John Honeyman. Washington then used this oportunity to have Honeyman give false information to Col. Rall and give Honeyman a key so that he could escape from the Guardhouse. Honeyman went to Rall, gave him the false information and that is how George Washington won the Battle of Trenton in 1776.
- In the Hunchback of Notre Dame stage musical (that's only been performed in Germany) Phoebus does this with Esmeralda when he allows her to escape.
- At the beginning of Half-Life 2, Barney is working undercover for the resistance as a Combine soldier. When he comes across Gordon, he justifies wanting to be alone with Gordon by implying to another (real) Combine guard he's going to beat/torture him. Then when the guard leaves Barney and Gordon alone, Barney clues Gordon in with exposition and then sends him in the right direction.
- Black Sigil uses this one and twists it just a tad. After being separated from the rest of the group, Aurora and Nephi are alone in Drakus Tat. Nephi (the local King) has to extract information from his loyal subjects (and Aurora is a known enemy of their master, Big Bad Forbidden), so he declares Aurora his slave and brings her to the dungeon to "break her in". He then calls in one of his minions to lure out the necessary intel in what the minions believe is his "interrogation" of Aurora.
- Near the end of Metal Gear Solid 2 Sons of Liberty, there is a torture sequence reminiscent of the first game that ends with Raiden being released by Olga Gurlukovich. She reveals that she was only helping the Patriots because they were holding her son hostage, and that she was the mysterious "Deepthroat" that assisted Raiden at several points in the story.
- In Watership Down, Bigwig shows an interest in Hyzanthlay and asks about her... but is told "I'd look elsewhere if I were you, she's a trouble-maker." Hyzanthlay was never imprisoned though, Efrafa was enough to a prison camp anyway to make the point moot. Keeping prisoners is not in Woundwort's nature anyway.
- Furthermore in the original novel, Bigwig takes advantage of the fact that his position as Owsla gives him freedom of sex, so when he asks for her to be brought to his burrow everyone merely assumes he meant to mate.
- Played straight with Bigwig convincing Blackavar that they are planning a breakout.
- Sokka tried to do this in Avatar: The Last Airbender, when he was deep undercover. Of course, most of the plan was not well thought out, so why start now?
- And she only ended up hitting him when he made to kiss her before revealing his identity (he was actually hoping to reveal himself with the kiss as a Call Back to something she had done), which she doesn't react well to, for obvious reasons.
- He also tried this with Zuko, whispering some information to him while pretending to beat him up.