History Main / SleepingWithTheBoss

[[quoteright:350:[[Series/MadMen https://static.tvtropes.org/pmwiki/pub/images/sleeping_with_the_boss.jpg]]]][[caption-width-right:350:I'm sorry, Mr. Draper is busy at the moment...]]

* Similar to ''Dragon Age'', ''Franchise/MassEffect'' can also have this come into play with relationships between Commander Shepard and any of their squadmates since they are the commanding officer on the ''Normandy''.

* ''Film/LiarLiar'': Jim Carrey's character is sleeping with his boss -- until the wish comes into effect and he makes a truthful (and uncomplimentary) comment about the sex they just had.

** [[https://www.youtube.com/watch?v=5g_qfVdo99A "My family made fun of my disability, until I became a CEO…"]] [sic]: [[spoiler:Sakiho had an affair with her boss and his wife's PI caught her red-handed and threatened to sue her. Therefore, she and her mom went to her grandparents' house to ask her now-CEO sister Misaki for money. However, she refused to give them money for all the abuse they put her through]].

* This trope is a favorite among the writers of ''VisualNovel/ChoicesStoriesYouPlay''. In ''{{VisualNovel/Bloodbound}}'', ''VisualNovel/HomeForTheHolidays'' and ''[[VisualNovel/OpenHeartChoices Open Heart]]'' for example, the DevelopersDesiredDate is the player character's boss. The same goes for ''VisualNovel/DistantShores'', as the main love interest is the captain of the pirate crew the player character is part of. ''[[VisualNovel/LawsofAttractionPixelberry Laws of Attraction]]'' also features the the player character's boss as one of the love interests.

* The ''Franchise/AceAttorney'' fandom is very fond of pairing up Phoenix with his assistant, Maya Fey.

* This trope is a favorite among the writers of ''VisualNovel/ChoicesStoriesYouPlay''. In ''{{VisualNovel/Bloodbound}}'', ''[[VisualNovel/HomeForTheHolidays]]'' and ''[[VisualNovel/OpenHeartChoices Open Heart]]'' for example, the DevelopersDesiredDate is the player character's boss. The same goes for ''VisualNovel/DistantShores'', as the main love interest is the captain of the pirate crew the player character is part of. ''[[VisualNovel/LawsofAttractionPixelberry Laws of Attraction]]'' also features the the player character's boss as one of the love interests.

* This trope is a favorite among the writers of ''VisualNovel/ChoicesStoriesYouPlay''. In ''{{VisualNovel/Bloodbound}}'' and ''[[VisualNovel/OpenHeartChoices Open Heart]]'' for example, the DevelopersDesiredDate is the player character's boss. The same goes for ''VisualNovel/DistantShores'', as the main love interest is the captain of the pirate crew the player character is part of. ''[[VisualNovel/LawsofAttractionPixelberry Laws of Attraction]]'' also features the the player character's boss as one of the love interests.

** Roger Sterling has a habit of sleeping with his secretaries. He most notably has a running on-and-off affair with Joan Holloway (who, while not ''his'' secretary, exactly, is still his subordinate in the sense that he's a partner in the firm while she is an employee). Roger even divorces his first wife, Mona, to marry his secretary Jane Siegel (who was about the same age as his daughter). It doesn't last.

* This is a frequent occurrence on ''Series/MadMen''.
** Roger Sterling has a habit of sleeping with his secretaries. He most notably had a running on-and-off affair with Joan (who was not ''his'' secretary, exactly, but she was still his subordinate in that he was a partner in the firm while she was an employee). Roger even divorced his first wife, Mona, to marry his secretary (who was about the same age as his daughter). It doesn't last.
** Don, ChivalrousPervert that he is, actually against this kind of relationship on principle (primarily for practical reasons, but he also has some ethical qualms about it). However, Don's principles went out the window in Season 4 (the one right after his divorce), and he started sleeping with his secretary Megan. He married her. It doesn't last, either.
** Peggy Olsen had a one-night stand with Pete Campbell when she was still a secretary. People also falsely assume that she was promoted to copywriter because she slept with Don; again, Don had a rule against that, which he was still following at the time she was promoted (Season 1).

** ''Series/{{Jessica Jones|2015}}'': In season 1, Jeri Hogarth is having an affair with her secretary Pam, while in the midst of a bitter divorce from her legal spouse Wendy. This one ends badly, as Jeri tries to have Kilgrave [[MindRape force Wendy to agree to lesser terms]], only for him to instead order Wendy to kill Jeri through DeathByAThousandCuts. Pam kills Wendy before she can get too far, but is subsequently arrested and breaks up with Jeri, now realizing what she truly is.

* ''Manga/BootyRoyaleNeverGoDownWithoutAFight'': Done by Kurisu with Yajima, [[RightHandHottie the assistant manager]] at the gravure modelling agency she works for. The first time happens during chapter 23, when Kurisu gets drunk and propositions Yajima for sex in his office. The second incident occurs during chapter 28, which starts with Kurisu playing footsie with his crotch under the table. Yajima excuses himself to the Men's room, only to have Kurisu follow him moments later and confront him about his feelings for her. Yajima finally relents, prompting a marathon session that last ''[[ExtremeLibido several hours]]''. She returns to the office wobbly legged by the time he's done with her.

* At the beginning of ''Series/MoneyHeist'', Arturo Román, the then-director of the Royal Mint of Spain and a married man, has had an affair relationship with his personal secretary Mónica Gaztambide for several years, with [[CharacterNarrator Tokyo narrating]] that Mónica had made him feel young again ever since his marriage to his wife Laura 14 years ago. By the end of the second season, he ends up losing both Laura and Mónica, the former once she discovered she had been cheating on him for a good while and thus filing a divorce from him, and the latter when she defects to the heist team after finding Denver to be a better boyfriend for her.

* At the beginning of ''Series/MoneyHeist'', Arturo Román, the then-director of the Royal Mint of Spain and a married man, has had an affair relationship with his personal secretary Mónica Gaztambide for several years.

* In ''[[Fanfic/HowStormerGotHerGrooveBack Painted Blind]]'', Stormer begins a relationship with Riot. Riot is technically her boss, though that's overshadowed by their musical rivalry

* ''Series/InterviewWithTheVampire2022'': At the beginning of [[Recap/InterviewWithTheVampire2022S1E2AfterThePhantomsOfYourFormerSelf the second episode]], Daniel Molloy has no evidence of any inappropriate behaviour between the personal assistant Rashid and his boss Louis de Pointe du Lac, yet his journalistic instincts sense that they may be in a sexual relationship, so Daniel invokes this trope when he asks Rashid, "I mean, is it only work or are you and he...?" Rashid's answer is cryptic because it's neither an affirmation nor a denial: "[[LikeAGodToMe I serve a god. It is my honor to serve.]]"

* Franchise/MarvelCinematicUniverse:
** ''Series/{{Jessica Jones|2015}}'': In season 1, Jeri Hogarth is having an affair with her secretary Pam, while in the midst of a bitter divorce from her legal spouse Wendy. This one ends badly, as Jeri tries to have Kilgrave [[MindRape force Wendy to agree to lesser terms]], only for him to instead order Wendy to kill Jeri through DeathByAThousandCuts. Pam kills Wendy before she can get too far, but is subsequently arrested and breaks up with Jeri, now realizing what she truly is.
** ''Series/{{Daredevil|2015}}'': In season 2, [[SexySecretary Karen Page]] briefly dates [[BlindJustice Matt Murdock]] before the strain of his double life as Daredevil and a number of misunderstandings (like Karen finding Elektra in Matt's bed and mistaking him for cheating on her) temporarily drive them apart. Many fanfics have theorized that Matt would have slept with Karen at the end of their first date in "Kinbaku", had he not turned down her inviting him up to her apartment after making out with her on the front steps of her building so he could go help Elektra.
** ''Series/{{Luke Cage|2016}}'': Luke Cage's mother Etta was seemingly unable to have children. So when Luke was born, he was seen by many as the "miracle baby". During the years before this, his father James Lucas engaged in an affair with his secretary Dana Stryker. The affair culminated in Dana giving birth to a son, [[BastardBastard Willis "Diamondback" Stryker]]. After Luke was born, Willis grew up resenting his legitimate half-brother over perceived {{parental favoritism}}, eventually driving him to frame Luke and throw him in Seagate.

* Eleanor on ''Series/GoodGirlsRevolt'' brings this up at a meeting, asking the researchers who’s slept with their boss, and then asking who’s slept with a man they weren’t sure was their boss or not (i.e. their reporter). There’s also something going on between [[spoiler:Patti and Finn, the editor-at-large, though we’ve only seen them kiss]].

* ''Series/TheLWord'': Jodi ends up in this situation when she's hired by the university as a professor, with her grilfriend Bette as the dean who's her superior. This gets awkward when they break up over Bette's cheating.

* In the ''Series/ThirtyRock'' episode "Jack-Tor", when Jenna is tricked into thinking layoffs at the show are eminent, she decides to sleep with one of Jack's bosses to secure her job. Unfortunately for her, it turns out the man was [[SubvertedTrope actually]] an actor playing Jack's boss for one of the show's skits.

* In the one shot [[{{Hentai}} h-manga]] ''Maldivian Flight,'' an heiress takes her butler with her on vacation so that he can provide his services to her, and when she convinces him to once again pleasure her, she laments that this may be their last time since her [[ArrangedMarriage parents agreed that she will marry the son of another wealthy family]] so that she can settle down and [[IWantGrandkids have kids like a proper lady should do]]. However, the heiress decides rather than this being their last time, she will instead convince her father to call off the marriage so that she can be with her butler, which her father refuses to allow as he's just a family servant, which is when the heiress' grandmother interjects and tells her son that she met her late husband when she was just a maid. After hearing this, the heiress' father decides to hear her out.

* In ''WesternAnimation/MoonbeamCity'', Detective Dazzle Novak and Police Chief Pizzaz Miller enjoy a yearly, weekend-long romantic tryst during the annual "Cop Con" gathering, which involves multiple instances of [[CoitusEnsues passionate love-making]]. The rest of the year, the two are [[BelligerentSexualTension mutually antagonistic]], with Dazzle [[JerkWithAHeartOfGold routinely disobeying]] Pizzaz's orders, and Pizzaz being [[AngerBornOfWorry repeatedly frustrated]] with Dazzle.