Sleeping with the Boss

I'm sorry, Mr. Draper is busy at the moment...

112. Never have sex with the boss's sister.
113. Always have sex with the boss.

— The Ferengi Rules of Acquisition

A sub-trope of Unequal Pairing and Office Romance, this is when a person in authority specifically gets "busy" with an employee or a member of their staff.

A favorite plot device in many a film, this usually takes on one of any given number of scenarios: the master of the house banging the maid, or the mistress of the house getting naughty with the pool boy or gardener, or the office manager having "business meetings" with his secretary while his wife remains unaware. Either party in the affair may be the instigator, though usually that role goes to the one who holds the greater power and authority. Usually, too, the boss or supervisor is older and more "experienced" than the employee.

If either party is married or in a relationship (which is usually, but not always, the case in this kind of situation), this kind of affair comes from an unfaithful heart; unsurprisingly, in such a case, this usually results in a Love Triangle and all the problems that come with it. If the employee is female and the boss is male and married, the employee may take the role of The Mistress. Or, in some cases, the wife/husband of either participant may know of the affair, but won't say or do anything about it because they want to keep up public appearances.

Since Power is Sexy, the employee is often perfectly happy with such an arrangement, and may even enjoy being ordered around and punished. However, this kind of situation also holds the risk of the employee eventually asking "Am I Just a Toy to You?", if the boss is flaunting their power over the employee just to satisfy a perpetually high libido. Or it may be a form of Sexual Extortion if the employee engages in sex with the boss under duress or blackmail (though the reverse can also be true, in that it's the employee who blackmails the boss).

Sometimes, the relationship is a part of the employee's strategy of Sleeping Their Way to the Top, advancing their career (or trying to) by seducing their superior. This doesn't mean their feelings are necessarily fake, though. The boss might be in the dark about it, or might know and just not care. Sometimes, it's the boss who decides to "reward" the employee, leading to Nepotism. Sleeping Their Way to the Top is thought to be especially common in showbusiness, leading to Casting Couch situations, when someone sleeps with the producer or director to land a starring role — though this, too, might sometimes cross into Sexual Extortion territory.

Whether the participants are single or are married to other people, this kind of scenario opens itself to some discrimination depending on the gender of the employee in the equation. If the employee is female and the boss is male, the woman may be seen as loose and only advancing her career by sleeping her way to the top, and she'll be branded by those who are aware of the relationship. If, however, the boss is female and the employee is male, then the man will be seen as extremely lucky; at worst, the situation may be given an indifferent shrug, or played for laughs if the boss is an Abhorrent Admirer.

This can also happen in the military, which adds to the additional point that the relationship is probably flat-out illegal on top of all other considerations. See Inappropriately Close Comrades for more.

Compare Pizza Boy Special Delivery, where the persons in question aren't in a permanent boss/employee relationship but still have sex in the midst of conducting an otherwise ordinary business transaction; and Teacher/Student Romance, where the relationship in question takes place between a teacher and a student (though sex may or may not be involved in this case).

Also compare Bodyguard Crush, where a person's appointed security guard harbors feelings for their client or vice versa that may or may not be reciprocated; Subordinate Excuse, where the employee uses their being employed by the boss as an excuse to exercise affection for said boss (though that situation may NOT necessarily automatically result in the two parties having sex); and Hired for Their Looks, where the boss appreciates the employee's decorative qualities but doesn't go beyond ogling.

Note that this trope is not the same situation as the Sex Slave, where the person with the lesser authority is in captivity and is forced to engage in sex under orders from their captors.

Also note that the Office Romance speaks more generally about inter-office relationships and can be (and usually is) applied to co-workers who are on equal standing; this trope is specifically about a sexual relationship between a boss and their employee. It should also be noted that, although use or abuse of power on the boss's part does sometimes play a role in this trope, it does not happen in all cases, as some instances of this are mutually consensual.

Far more egregious and likely to result in retribution from the boss's end would be Sleeping with the Boss's Wife.

No, this isn't about video game Boss Battles.

noreallife

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Examples:

Anime & Manga

• Berserk: Casca and Guts have a Relationship Upgrade and Their First Time after she's been promoted to leader of the Band of the Hawk in Griffith's absence, making theirs a boss-employee romance after a fashion. There was no coercion or ulterior motive on either part and they're in a serious relationship, but it does cause some tension later during the rescue operation when they argue with each other about having to put their feelings aside for the mission.
  • Interestingly, Casca was at one point accused of sleeping with Griffith to get her high position in their army. In actual fact, her feelings toward him ping-ponged between a hopeless crush and Hero Worship, but never went further than that.
• Booty Royale: Never Go Down Without a Fight!: Done by Kurisu with Yajima, 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 several hours. She returns to the office wobbly legged by the time he's done with her.
• In Chainsaw Man, Denji's boss Makima was a Fetishized Abuser who used the promise of sexual favors to manipulate him into doing her bidding, with him being so starved for affection that he initially either doesn't notice or doesn't care.
• Don't Meddle with My Daughter!:
  • Chapter 6 features a three-page montage scene of Point Blank having sex with Zenovia. After he exits her bedchamber, a pair grunts asks if he's done nailing their queen and notes that he seems to be her favorite; implying it wasn't their first time.
  • Artemis ends up in a similar arrangement with Blue Skull. Her bio in "Honey, Hold me Tightly!" says she's subservient to him and acts as his bodyguard. But he implies that he regularly sleeps with her, in what he calls their "therapy" sessions. It was eventually confirmed in the doujinshi epilogue series when they were given a page spread in "MILF of Steel: Forever".
• A massive Parental Bonus in HuGtto! Pretty Cure is that the villains of the season—Criasu Corporation—display a toxic work environment that adult viewers would be familiar with. One standout example is implication that the Big Bad George Cry abuses his power as the president of the company to engage in this trope with multiple employees. At the very least, it is known that Pupple considered George to be her boyfriend and was distraught when she found him having an affair with Gelos.
• In the one shot h-manga Maldivian Flight, an heiress named Ayako takes Sousuke, 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 parents agreed that she will marry the son of another wealthy family so that she can settle down and have kids like a proper lady should do. However, when they finish, Ayako 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 Sousuke. When they return from the trip, her father refuses to entertain the idea of Ayako and Sousuke being together because he's just a family servant, which is when Yasuko, Ayako's grandmother, interjects and tells her son that she met her husband/his father when she was just a maid. After hearing this, Ayakos's father decides to hear her out the young couple.
• Talia did this with Old Flame Chairman Durandal, under whose authority she helms the flagship in Mobile Suit Gundam SEED Destiny. She does end up trying to assassinate him at the end, but that's more for his general Jerkass and Dark Messiah qualities — aside from WMD'ing their own troops — than anything about their relationship, which isn't well-developed outside of one depicted instance of this, a Flashback breakup scene years prior to their current positions, and a lot of him pissing her off.
• Phantom Quest Corp.: In Incident File 03, Mr. Nagasuki gets caught in the act of having sex with his secretary, when Detective Karino drops by his office to question him. Nagasuki and his secretary are later shown in bed together at his condo.
• Princess Lover!: In the 2-part H-OVA, Teppei only fantasizes about his maid, Yuu Fujikura, giving him fellatio. But, in the VN's themselves, Teppei actually sleeps with her midway through her character route, which ends with her being pregnant with his child.
• In The Rose of Versailles, this is how Jeanne Valois was born, as her mother, Nicole Lamoriere, was a maid at the castle of Jacques de Valois, Baron de Saint-Rémy, when they were conceived, leaving her in the position to adopt Rosalie when Martine Gabrielle de Polastron, the future Duchess of Polignac, got pregnant out of wedlock while at the castle and had to give her daughter Rosalie away.
• Happened many times in Sakura Gari, before the series starts. Souma is the handsome leader of the rich Saiki family, and he often takes loves among the younger maids and boarding students/butlers ^note (high school/college-aged young men who work as servants in Big Fancy Houses during the Taishou Era, in exchange for academic/economic help from the main families); all of them meet rather screwed up ends after being harassed, tortured and, in one case at least, murdered by Souma's sibling Sakurako. This also makes the plot of the series itself, as the protagonist of the series is a boy named Masataka who is employed at the Saiki house, and later Souma starts to make passes at him...
• Variable Geo: It's implied that Reimi Jahana sleeps with her personal aide, Washio. Such as when Chiho found Reimi straddling him while they were making out. A later scene has him deliver a brief report to Reimi, which concludes with this exchange:
  Reimi: (while driving) "Washio..."
  Washio: "Yes, Madam Reimi...?"
  Reimi: "You're spending the night with me."
  Washio: (smiles shyly and blushes) "Yes, of course."
• In YuYu Hakusho, Kurama's mother was in a relationship with her boss. It was an honest courtship, and they eventually marry.

Comic Books

• The Boys has Billy and Rayner the CIA director, though it's not so much a relationship as it is vitriolic, self-imposed hate sex.
• In Chew, Tony's coworker Colby sleeps with his and Tony's Mean Boss Applebee (to get Applebee off their backs) and later with his USDA boss.
• Red Ears: A female office worker keeps getting called in by her boss every hour for a "special meeting" until she finally gets sick of it. The last two panels show her with a sticky white substance in her hair that one of her colleagues comments on, leading to the punchline "See, I don't just swallow everything from him!"
• Wonder Woman Vol 1: Dr. Lana Kurree's boyfriend works for her, and is using her and her affection towards him to try to advance his own career. This comes to light when he poisons a patient who had been a successful test case of a cancer treating drug and tries to steal her research and notes on the drug in question.

Fan Works

• Baby Boom (Shawna Canon): After an Aliens Made Them Do It incident in Chapter 1, Gabriel Agreste's thoughts on hiring employees just to have sex with them, is noted:
  Hearing [his secretary] address him that way, looking as prim and business-like as ever, after what had just happened made him feel like one of those despicable men who used their secretaries like their own personal whores. Gabriel Agreste was not one of those men.
• It's mentioned in Chaos and the Aftermath that Samus has had sex with her employers in the past.
• I Hope You're Prepared For An Unforgettable Wedding!: Principal Skinner and Superintendent Chalmers' relationship is a mutually consensual, positively-portrayed example of this. Even though Chalmers is Skinner's boss, the two of them fell in love and entered a sexual relationship.
• A rare female on female example in Love Hina fanfic Contract Labor with Motoko and her boss Kotoko.
• Mended combines this with Teacher/Student Romance. Around twenty years ago, Delia began working as assistant of Professor Oak's post-university, after also having been his student as a teenager. Oak was attracted to her but kept his distance until Delia caught her husband Will cheating. After Will ran off with his ex, Delia couldn't afford her apartment so Oak offered the room above his lab to her. They became quickly friends, but one day they gave in to their mutual attraction. Delia ended up pregnant with Ash afterwards. They've been in a Secret Relationship behind Ash's back his entire life, until at seventeen when Ash discovers that Professor Oak is his dad. It was secret more because Delia was technically Oak's student rather than because of the "boss" element of their relationship. Delia wanted to avoid scandal.
• Mob Psycho 100 Any fic that pairs Reigen and Serizawa. It's usually lampshaded, too, such as in Apparitions Gone Awry
  Reigen: I'm sure your boss will be forgiving if you're a little late. [laughs] I heard he’s got a real weak spot for you.
• Horde Champion: Anevay is sleeping with her commanding officer, and later her Warchief.
• How Stormer Got Her Groove Back: In "Painted Blind", Stormer begins a relationship with Riot. Riot is technically her boss, though that's overshadowed by their musical rivalry
• Mob boss Violet Kincaid tried her hardest to make it happen with Roman Torchwick in Roman's Empire when he still worked for her (everything short of forcing him into it), but he refused to bite. He does admit that she's attractive, but he declines on the basis that it would be unprofessional and the fact that she's about thirty years older than him.
• In the second chapter of A Song of Grumbling & Cotton Candy, Pizzazz finds Jerrica's belongings in Jem's room. She comes to the conclusion that Jem and her manager Jerrica are ex-girlfriends, not realizing that Jerrica is Jem. Jem goes along with it by claiming she broke up with Jerrica because their relationship was unprofessional.
• Vale's Underground: A rare example with a female boss and a male subordinate. Cinder is portrayed as a mob boss and she has a casual sexual relationship with her personal hitman, Mercury Black. This is common knowledge in the criminal element. And while they don't broadcast it to everyone, neither of them actually make any effort to hide it either. Both of them even openly make quips about it.
• In What Tomorrow Brings, Tom implies that Feriss 512's relationship with Visser Three was sexual. Since neither he nor Alloran consented to it, he understandably doesn't like to talk about it.
• Vow of Nudity: Fiora seems to have a bad habit of sleeping with authority figures. In her first story, she seduces her university professor to become his academic assistant, and in her second story she seduces her clan's matriarch in the hopes of learning magic. In both cases, it blows up in her face and leads to even-worse choices.

Films — Live-Action

• Subverted to comic effect in Boomerang, when Marcus (Eddie Murphy) sleeps with Lady Eloise (Eartha Kitt), the elderly namesake of the company who just acquired his company. The next day, he boasts to Angela,(Robin Givens), that he's got the inside track for the upcoming promotion. At which point, Angela breaks it to him that Lady Eloise hasn't been involved with the company for years and is just a figurehead with no power.
• This is a significant driver for the plot of Bridget Jones' Diary (that and the Belligerent Sexual Tension with the other love interest).
• In City Slickers, a checkout girl from Phil's store breaks into a party he's attending to tell him she's pregnant, so this trope has been in play. Played both for drama, and laughs:
  Ed: ...that's pretty smug advice, coming from a man who mounted an eighteen-year-old checkout girl on the day-old bread rack.
  Phil: She's twenty - and shut up.
  Ed: Let me get you hot, Phil: "I need a price. Register Nine, I need a price..."
  Phil: Cut it out!
  Mitch: (warningly) Guys...
  Ed: What did you use for protection, paper or plastic?
• Cut to the Chase: It's revealed Izzy was seeing her boss, the DA, who was also married.
• The movie Disclosure plays the "female boss, male employee" version of this for all the drama it can. Meredith Johnson, the ex and new boss of Tom Sanders, tries to restart their relationship, but Tom doesn't want to go through with it due to him being married now. Meredith then out-and-out tries to rape him, forcing him to fight her off. The plot gets kicked off when she files charges of sexual harassment against him. When his lawyer investigates her, she finds that several of her male subordinates have abruptly and inexplicably quit, heavily implying that Tom is neither the first nor only employee that she's made unwanted advances to.
• Fair Play: Throughout the film Luke insinuates that Campbell being attracted to Emily in some way played a part in her promotion, and finally accuses her of trading sexual favors for it. Emily explodes, saying that he can't accept that she earned that job all on her own without her good looks playing a part.
• A particularly grim and sleazy version in Feast. Tuffy doesn't want to and doesn't enjoy it, but she has a kid to feed, so whenever Bossman is stoned and horny, it's time to bend over his desk and "take a meeting".
• Fear City: Nicky is in a relationship with one of his strippers, but it's apparently a loving one. She also says to him that she doesn't expect any special favors because of the way it will make her look to the other girls.
• Flashdance: Alex starts a romance with Nick, the owner of the steel mill she works at.
• Grand Canyon: Secretary Dee had a one-night stand with her boss, attorney Mack. The aftermath of this encounter drives Dee's character arc in the film.
• The Wesley Snipes film Jungle Fever has this as the trigger for its main plot, in which Snipes' character sleeps with his secretary despite him being a married man and her already being in a relationship. It's more remembered and criticized in-universe for the fact that he's black and she's white.
• This turns out to be a major plot point in Lakeview Terrace. Turner's wife was having an affair with her white boss, and they died in a car accident together. The affair resulted in Turner hating interracial couples, and it's the reason he harasses the lead couple.
• Liar Liar: Fletcher's immediate law firm boss, Miranda, seduces him into bed with her after being impressed by his Amoral Attorney skills. However, that interest turns sour the moment the wish on Fletcher comes into effect as it results in him making a truthful uncomplimentary comment about the sex they just had.
• This is the status of Tony and Pepper's relationship from the finale of Iron Man 2, throughout the rest of the Marvel Cinematic Universe, until some unknown point between the events of Avengers: Age of Ultron and Captain America: Civil War.
• In 9 to 5, Doralee is accused of doing this, and Judy makes it look like that's what she's doing (with the added bonus of BDSM) in order to get rid of her ex-husband Dick.
• Please Turn Over:
  • After reading Naked Revolt, Mr. Jones and Janet are convinced that Edward is having an affair with his secretary, Miss Jones.
  • Stella from Naked Revolt sleeps with her boss Roger so he'll buy all sorts of expensive things for her:
    Blanche: You dare to suggest that... my father... and you, his secretary-?
    Stella: Confidential secretary, cookie. Hmm, very confidential.
• By seducing the chairman of Omni Consumer Products in RoboCop 2, OCP psychologist Juliette Faxx is able to railroad her project through development.
• Scanners III: The Takeover: After Helena takes over her father's company, she schedules an "appointment" with one of her younger execs at her house. It's at this point that she happens to realize that her psychic abilities also work through television signals, and uses him as a guinea pig for this purpose.
• In the Michael J. Fox film The Secret of My Success, Howard Prescott, CEO of the Pemrose Corporation and the main character's uncle, has an ongoing affair with Christy, one of his employees and the main character's Love Interest.
• This forms the plot of Secretary, where Lee and her boss Edward engage in a sadomasochistic relationship.
• Showgirls: Nomi eventually sleeps with her new stage boss to get ahead (she had already given him a lap dance when she was still a stripper and not employed by him). The other girls call her out on this, because they have an unwritten rule against it, though it's implied at least some of them have also broken this rule.
• In Son of the Stars, Zhengzheng starts a relationship with her supervisor Hong Jin, who promotes her, to the anger of some of her coworkers, and lets her move into his nice apartment. They break up because Hong doesn't want an autistic stepson.
• Played for laughs in Spies Like Us, when Fitzhume tells his coworker that he's arranged an intimate lunch with the boss. Cut to Fitzhume and his attractive boss in bed. And apparently, he just arranged the "intimate lunch" to try to talk his boss into finding a way for him to not take the Foreign Service Board test.
• This is the standard way to land a husband in the world of Thoroughly Modern Millie (give or take actual sex): you meet a successful man by becoming his secretary, then he falls in love with you and you get married.

Literature

• The Bible:
  • Abram (shortly before his name was changed to Abraham) slept with his Egyptian maid Hagar in order to have a child, with encouragement from his wife Sarai (later renamed Sarah) since she couldn't have children of her own. Unfortunately, since God had specifically told Abram that he would have children with Sarai, this plan backfires horribly — Hagar starts forgetting her place with Sarai and is eventually thrown out with her son, Ishmael, though God helps them out later. (Ishmael is said to have become the ancestor of the Arabian people)
  • There's also a subversion with Joseph, at the time a slave in Egypt under the employment of Potiphar. His master's wife wanted to screw him physically, but he rebuffed her advances on the grounds that she was already married and that giving in to her would be a sin against God. So she chose to screw him metaphorically.
    Joseph: How then could I do this most wicked thing, and sin before God?
• In Bone Song by John Meaney, the protagonist has a passionate romance with his female boss (who also happens to be a zombie woman). Unlike most cases, they are genuinely in love with each other, and their relationship is undeterred neither by their professional status nor by the fact that she's undead.
• In Dragon Bones, the noble Garranon sleeps with the king. In the sequel, Dragon Blood, the king becomes interested in his court mage. It is revealed that Garranon sleeps with the king only to keep his family safe and that it has been going on since he was fifteen, making this overlap with Sex Slave.
• The Mister revolves around a playboy earl falling for his housemaid, who is hiding a Dark and Troubled Past.
• Both Anne and Raphael from My Next Life as a Villainess: All Routes Lead to Doom! were born from a nobleman sleeping with one of their maids. The former was conceived during the short period of time her mother was serving as her father's mistress, while in the case of the latter their father used their position to force their mother to sleep with them.
• In the Jamaican play Old Story Time, this is one of the major revelations made toward the end of the story, involving two major characters. George Murchison (the boss) coerced Lois (his secretary at the time) to engage in physical relations with him, in exchange for covering up her misuse of bank funds to finance her then-fiance Leonard's education.
• An expanded-universe Star Trek supplement, The Ferengi Rules of Acquisition, lists Rule 113 as "Always sleep with the boss." Interesting when one recalls (and a later commentary book on the rules points out) that in traditional Ferengi culture (barring interspecies employment), all bosses and employees are male.
• Anthony Winkler's works:
  • In The Duppy, Baps recalls that he slept with five of his maids.
  • Barrister Fitzpatrick in The Great Yacht Race sleeps with his secretary Lilly, and the hotelier O'Hara is carrying on a secret affair with his maid Iris. Father Huck later gets it on with his housekeeper, Missus Grandison.
  • In his autobiographical Going Home to Teach, Winkler recalls how his maternal uncles, all shopkeepers, often slept with their female employees.
• Something to Talk About: Jo and Emma, her assistant, are perceived as dating. It's not true, but the gossip outlets play up the idea nonetheless.
• Shock Point: A year ago, Cassie and her mother Jackie lived in a duplex in Minor. Then Psycho Psychologist Rick hired Jackie as his study coordinator. Before Cassie knew it, Rick had become her Wicked Stepfather and moved the family to Portland. Cassie thinks he wanted to flee Minor so his patients' families won't find out what he'd done. Jackie eventually realizes that Rick only pretended to love her to stop her from asking questions about his unethical behavior. Jackie was so starved for male attention, especially from someone as charming as Rick, that she made an easy mark.

Live-Action TV

• In the 30 Rock 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 actually an actor playing Jack's boss for one of the show's skits.
• Acapulco: Hector is hooking up with the resort owner Diane, which lands him a promotion to pool manager.
• In 'Allo 'Allo!, the long list of women that Rene sleeps with includes every female member of his cafe's staff other than his wife.
• Arrow
  • After becoming manager of Verdant, Thea Queen gives her boyfriend Roy Harper a job there. In fairness she offered him the job before she was either his boss or lover (back when her brother owned Verdant), to draw Roy away from his life of crime.
    Thea: Keep in mind, I do control your paycheck and your sex life.
  • Felicity Smoak and Ray Palmer, technically. He is her boss, seeing as he's the CEO of Palmer Technologies and he hired her, but she's his vice-president and they work together more as equals than as anything else.
• Behind Her Eyes: The protagonist strikes up a flirtation with a handsome stranger she meets in a bar only to find out he's her married boss. They try to resist each other, but they can't.
• The plot of the Turkish Soap Opera Binbir Gece is kicked off by a mix of this trope and Healthcare Motivation, as the widowed protagonist Sherzat will get the money she needs for her son's treatment from her very handsome boss Onur... but only if she sleeps with him.
• Cam and Arastoo on Bones technically. Brennan is his direct supervisor since he’s an intern but Cam runs the lab and is the overall boss. It’s less of an issue later in the series when Arastoo gets his doctorate and is more consultant than intern.
• Breaking Bad
  • Skyler White does this with her boss Ted Beneke. It's much less about any particular romance between them and much more about getting revenge on her increasingly criminal husband, though, and the power equation changes when it becomes clear that Ted is something of an irresponsible twit, driving her back to Walt.
  • Subverted in season 3. Walter tries to put the moves on his own boss Principal Carmen in retribution for Skyler's affair. However, while Ted and Skyler already had Unresolved Sexual Tension between them, there wasn't even a hint that either Walter or Carmen were attracted to one another, so his out of the blue attempt to seduce her just comes across as weird and pathetic. Rather than turning the cheating into a mutual affair, he is fired from his job as a teacher.
• In Charmed (1998), Jason Dean actually bought the paper where Phoebe works to set up this scenario. Well, meeting and seducing her was at least part of his motivation. He did directly leverage his position by making her write an article defending online dating because she hadn't responded to his profile.
• Cheers: Sam hooks up with his waitress Diane at the end of season 1 (resolving the UST), and they almost get married at the end of season 5.
• CSI had Grissom and Sara, although much has changed since he left and she left, then returned.
• Throughout Season 2 up to early Season 4 of Drop Dead Diva, Kim Kasswell dated on and off Jay Parker, the managing partner.
• Dexter:
  • Debra Morgan, a detective at Homicide of Miami Metro Police Department, starts sleeping with and falls in love with Agent Lundy, their task force leader in season 2. He's actually an FBI agent and not her usual direct superior. Deb wants to keep their relationship secret at first but Lundy says it always gets out and that it's better to be honest right from the start. She wants to stay with him but they break up when she realizes they won't manage to make their long-distance relationship work.
  • Lieutenant Maria LaGuerta, a boss of Homicide, and Sergeant Angel Batista, her direct subordinate, start a sexual affair in season 4. Their superior Captain Matthews wants them to either break up or have Angel transferred to another department. They decide to marry and the pro-family politics allows them to stay together and both at Homicide department. Season 6 begins with them being Amicably Divorced.
• In El embarcadero, Katia has a long-standing affair with Big Boss. However, unlike most examples of this trope, the power dynamic isn't really an issue, and for the most part their affair doesn't affect their work.
• A significant arc in a later season of Friends saw Rachel sleeping with her male secretary, Tag.
• Eleanor on Good Girls Revolt 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 Patti and Finn, the editor-at-large, though we've only seen them kiss.
• In the Season 5 finale of House, the titular doctor winds up having sex with Lisa Cuddy, the hospital administrator and his immediate supervisor, after she comes over to his house to help him kick his Vicodin addiction. Except their encounter that night never actually happened—it was all a Vicodin-induced hallucination on House's part.
• Interview with the Vampire (2022): At the beginning of "...After the Phantoms of Your Former Self", 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: "I serve a god. It is my honor to serve."
• Las Vegas: Monica, the megalomaniacal new owner of the Montecito in Season 3, tries to seduce Danny McCoy after promoting him to President of Operations in Ed's absence. Danny isn't interested in the slightest and starts to conspire with Ed to have her removed.
• Jack McCoy of Law & Order is notorious for having had this kind of relationship with his assistants, all female. When he first came into the District Attorney's office in the original series, Claire Kincaid pointed out that he'd slept with all three of his previous assistants (and married one of them), to which Jack replied that all the relationships were mutually consensual. Then Claire declared that nothing of the sort would happen between herself and Jack, to which he agreed... only for them to get intimate later on down the line. However, the fact that they did become intimate wasn't revealed in the show until after Claire's death.
  • Claire had previously had an affair with a judge that she clerked for. As it turned out he had a criminally bad way of dealing with breakups.
• Across the pond on Law & Order: UK, James Steel (who was given McCoy's habit of bedding his colleagues) and his subordinate Alesha Philips had considerable Unresolved Sexual Tension, to the point where their final scene made it obvious that he deeply regretted never trying to make a go of it.
• After Lois & Clark got married, one episode saw Lois being promoted to the Daily Planet's editor. Clark jokingly says he's looking forward to sleeping with the boss.
• The L Word: 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.
• Mad Men: This happens a lot around Sterling Cooper.
  • 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 is about the same age as his daughter). It doesn't last.
  • Don Draper, Chivalrous Pervert that he is, 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 go out the window in Season 4 (following his divorce from Betty), and he starts sleeping with his secretary Megan, and eventually marries her. It doesn't last, either.
  • Peggy Olsen has a one-night stand with Pete Campbell while she is still a secretary. People also falsely assume that she was promoted to copywriter because she slept with Don; again, Don has a rule against that, which he was still following at the time she was promoted (Season 1).
  • Megan is propositioned by her female boss when she gets an acting job on a soap opera.
• Marvel Cinematic Universe:
  • Jessica Jones: 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 force Wendy to agree to lesser terms, only for him to instead order Wendy to kill Jeri through Death by a Thousand Cuts. Pam kills Wendy before she can get too far, but is subsequently arrested and breaks up with Jeri, now that she's seen Jeri's true colors.
  • Daredevil: In season 2, Karen Page briefly dates 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.
  • Luke Cage: 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, 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.
• Shows up a few times on Midsomer Murders, whether as "sleeping up the ladder" or actual romance.
• At the beginning of Money Heist, 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 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 filed a divorce from him, and the latter when she defects to the heist team after finding Denver to be a better boyfriend for her.
• In The Nanny, after four seasons' worth of Unresolved Sexual Tension between Fran and her boss Maxwell, they almost wind up sleeping together while in Paris, during the Season 4 finale...but Maxwell backs out of it at the last moment, offending Fran.
• On NewsRadio, news director Dave had an on-going relationship with reporter Lisa. For most of his first day she was his boss (everybody assumed he was a new sports reporter) and had every expectation of being named the new news director. She didn't take the revelation of him being her new boss well. (It eventually became clear their relationship resulted from her channeling anger into sexual arousal, but they still ended up as a surprisingly stable and generally supportive couple.)
• The Office (US) has Michael's rather rocky extended relationship with his boss Jan.
• This is a major plot point in seasons 3 and 4 of Parks and Recreation. Leslie and Ben, technically her superior, have UST from the beginning of season 3. However, it is revealed in "Soulmates", that Chris, the city manager (who is everyone's boss), has a rule against employees dating their superiors. Thus Leslie is afraid to act on their sexual tension until 4 episodes later in "Road Trip". They manage to have a Secret Relationship, until the season 4 premiere where Leslie decides to run for city council, where they mutually decide to break up. Chris finds out about them and in "The Trial of Leslie Knope", Ben ends up quitting his job so that Leslie isn't fired.
• In an episode of Quantum Leap where for the first time Sam leaps into a woman, his task of the episode is to keep a fellow secretary from committing suicide. The other secretary thinks that her boss is going to leave his wife for her; the wife informs the secretary in no uncertain terms that she's OK with her husband fooling around but she will not under any circumstances allow a divorce. It's also implied that she is the boss's second wife, and he met her when she was his secretary. When the secretary learns this, she tries to jump off a building but Sam talks her down.
• In the Seinfeld episode "The Maid", Jerry starts sleeping with the new maid he had hired. Unfortunately, this distracts the maid from doing any cleaning in the house at all and Jerry starts to think that he is paying a whore which the rest of the gang makes fun of. After he accidentally offends the maid with this statement, the maid breaks up with him and quits her job.
• On Showtime's Shameless (US), Fiona gets a low-paying job at a supermarket, and soon learns that most of her co-workers have been pressured into having sexual relations with the boss, Bobby. When she gets them all together to talk about it, some of them even defend it.
• Six Feet Under: This happens between Kroehner's Matthew Gilardi and his boss. It doesn't stop her from firing him for incompetence.
• The Thin Blue Line has Police Inspector Fowler paired with live-in girlfriend Sergeant Dawkins. Although given Fowler's outlook on his duties however, this is not a major issue. At one point he offers Dawkins some advice, half now (as her senior officer) and half when he is on break (as her boyfriend, as he is not being paid to advise people as their boyfriends and so cannot due so during work hours.)
• The Wheel of Time (2021): It turns out that Moiraine and Siuan, who's the head of the Aes Sedai which both belong to, are lovers. They keep this secret seemingly to avoid accusations of nepotism toward Moiraine.
• In Without a Trace, Samantha Spade had a brief sexual affair with her supervisor, Jack Malone. It resulted in his marriage dissolving. They rekindled it in the last season, but she ended it in the final minutes of the series finale to make things work with her son's father.

Radio

• In Jack and Millie, Millie's friend Shirley is devastated when her husband Harvey runs off with his PA. Jack tells Millie that Shirley should be glad to get rid of such a boring man, and when Millie says he obviously wasn't that boring after all, retorts that running off with your PA isn't interesting, it's cliche, and she probably completed the cliche by being half his age. Millie says he was around the same age as Harvey, and Jack concedes that maybe Harvey is slightly less boring than he thought.

Tabletop Games

• Shadowrun supplement Tir Na Nog. In the title country (the country formerly known as Ireland) Junior Minister Patrick Flanagan was videotaped having sex with his curvaceous redheaded secretary in his office.

Video Games

• Nadia Zelenkov in Command & Conquer: Red Alert is one of Stalin's advisors, and also his lover. She's actually The Mole for Kane, and kills Stalin after a Soviet victory.
• Technically the case for any of the Love Interests in Dragon Age: Origins, Dragon Age II, and Dragon Age: Inquisition, since the player characters of those games are the leaders of their respective Ragtag Bunch of Misfits, and the games (usually) require sex to take place before the romance is considered official.^note Sebastian in Dragon Age II and Josephine and Solas in Inquisition do not have sex scenes; if Sebastian is romanced on a friendship path, his romance is stated to be explicitly chaste. It is possible to romance Dorian without sleeping with him in a cutscene, but there is still suggestive party banter of the typical 'discussing the protagonist's sex life' style.
  • In Origins, if the player romances Alistair, Oghren explicitly invokes the trope in party banter with Al. "So... you and the boss, huh?"
  • Also found in Dragon Age II if Hawke helps Aveline romance Guardsman Donnic, as she's the captain of Kirkwall's defenses and he's one of her soldiers. In this example, however, the sex is only implied because Aveline and Donnic get married.
  • Similarly to Oghren, Cabot the bartender will call attention to the trope in Inquisition. One of his random comments, should he be asked about the mood in Skyhold after the romance is confirmed, is to tell the Inquisitor that some people are grumbling about "you having time to bed your allies." He then assures them that "I don't judge. Much."
  • There's another in-universe example in the background of Inquisition, and a rare female/female example at that; the Empress of Orlais had a lengthy affair with her elven servant Briala. The tie-in novel The Masked Empire introduces the relationship, which can be factored into the outcome of the peace talks in the game.
• If the Dragonborn in The Elder Scrolls V: Skyrim becomes Harbinger of the Companions, Arch-mage of the College of Winterhold, Guildmaster of the Thieves' Guild, and/or Listener of the Dark Brotherhood, and proceeds to romance/marry any of the faction members of the groups they lead, this trope is technically in play.
• Mass Effect can have this come into play with relationships between Commander Shepard and any of their squadmates, since Shepard is the commanding officer on the Normandy.
• In many class storylines of Star Wars: The Old Republic, you can romance your companions and technically, most of available companions are subordinates of the Player Character. Elara Dorne, the Republic Trooper's companion, even lampshades this, observing that intimate relationships between a commanding officer and a subordinate are forbidden by military regulations, but reciprocates your advances, anyway. Elara, being Elara, finds and submits official paperwork that authorizes the relationship.

Visual Novels

• This trope is a favorite among the writers of Choices: Stories You Play. In Bloodbound, Home for the Holidays and Open Heart for example, the Developers' Desired Date is the player character's boss. The same goes for Distant Shores, as the main love interest is the captain of the pirate crew the player character is part of. Laws of Attraction also features the player character's boss as one of the love interests.
• Besides Amanda, the protagonist of Daughter for Dessert can sleep with his other employees (Kathy, Heidi, and Lily) as well.

Web Animation

• Manga-Waido: In this story, Aya became known for this at her part-time job, but she dumped the man when his wife and sister-in-law held her accountable. Her fling broke the couple apart and the ex-wife fell into depression, for which her younger sister wants to make Aya pay.
• MoniRobo:
  • "My toxic sister tried to ruin my wedding…": At Miyu's wedding day, the groom reveals that her seemingly successful and dignified older sister had an affair with her boss, on top of sleeping with other guys and even asking the groom out before he met Miyu. Since she tried to ruin Miyu's wedding and snatch her husband, he decided to tell everyone about her secret, effectively making the older sister a pariah.
  • "My family made fun of my disability, until I became a CEO…" [sic]: 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—the "made fun of my disability" part of the title refers to this, and this is why she lives with her grandparents.
  • "Exposing a slacking worker during lockdown. What the camera showed was shocking!": Yahata turned out to have slept with one of the company's higher-ups, which was the reason Masayoshi's aunt sent him to take care of her in the first place. When he finally exposed her affair in an online meeting, they reported her to another superior, which resulted in the lovebirds getting fired on top of the former superior's wife suing Yahata for alimony.
• Revenge Films: In My oldest sister was so scary when my other sister had an affair, A slept with her boss when she started working, which came to light when he had to be rushed to the hospital and she had to accompany him. However, she didn't want to because B, her older sister, worked there. Sister B got furious at A for it, as well as the boss's wife when she demanded A to pay for the affair.

Web Comics

• Big Break (2019): Yazmin, the owner of a bakery, often has sexual flings with her dishwasher Joseph, who she hired mostly because she found him very attractive.
• El Goonish Shive: Mr. Verres's personal assistant, Lavender, definitely has feelings for him. And as of the arc with the Working Title "Title Pending", it looks like he's started to reciprocate.
• This is a fundamental part of Erfworld culture, since a commander can give his units any order, including "take off all your clothes", and they'll obey it. This really Squicks Parson out.
• Invoked several times on Something*Positive: Kharisma makes no secret that she'll sleep with anyone for advancement (and is later fired without ceremony when the boss's fetish goes from redheads to blondes), while Monette is accused of this by an older, uglier coworker.
  Co-worker: At least all that lying on your back must have done wonders for your posture.
  Monette: Well, seeing as your method gave you bad knees and rancid breath, I figured I'd do it differently.
• Sumin works at a game development company in What Does the Fox Say. She has a sexual relationship with her boss Seju. Seju just so happens to also be her ex-girlfriend, who is also still in love with her.

Western Animation

• In Moonbeam City, 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 passionate love-making. The rest of the year, the two are mutually antagonistic, with Dazzle routinely disobeying Pizzaz's orders, and Pizzaz being repeatedly frustrated with Dazzle.
• Becomes a plot point in The Simpsons episode "Grade School Confidential", where Principal Skinner and Mrs. Krabappel enter a relationship, but have to keep it secret because a principal dating one of the teachers at his school would be considered a "conflict of interest".
• Played for laughs in South Park, in which PC Principal and his vice-principal Strong Woman get into a relationship that they have to keep secret due to the implications of this trope despite the fact that it is a fully consensual relationship between two adults. Even in later seasons where the two of them are raising kids they're still trying to keep it secret.

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