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Anime & Manga
- Inverted in K: Countdown, a manga that takes place between the movie and season 2, where Munakata invites Awashima and Fushimi to his family's home for dinner. It's very awkward, but in the end, the two of them come to understand him better and bridge that gap.
- Monica's Gang: Maggy's Dad's boss once had dinner with her family and she was told to control herself. Easier said than done. Maggy's Dad was afraid he'd be punished but instead his boss gave him a raise so he'd be able to support her.
- The "Dead-End Kids" arc of Runaways opens with the team having dinner with The Kingpin, who's hired them to steal something on behalf of a third party.
- Occasionally happens in Blondie.
- In Dilbert, Dilbert was once randomly chosen to have lunch with one of his company's executives. Dilbert took the opportunity to criticize the executive after the executive asked him to be honest (though he was really just fishing for compliments). He angrily started a Food Fight by flinging au gratin potatoes at Dilbert. Dilbert countered with an ear of corn in his hand unintentionally killing the guy when the corn knocked him out and he drowned in his soup.
- Calvin and Hobbes: The Series mentions one of these, but it's never actually shown.
- The film version of A Dog's Purpose has one of these be spoiled when Bailey (a dog) eats the prize coin of the dad's collection, a rare golden eagle, which he naturally boasts of to his boss and wishes to show off. Ethan gets Bailey to poop out the coin and returns just as they're about to open the case, so he distracts the adults by pretending to see a rat which Bailey tries to chase leading to a series of pratfalls and the boss and his wife storming out in disgust.
- The Judy Blume novel Tales of a Fourth Grade Nothing has this, only rather than the boss, it's a client at an advertising agency. The defiant kid brother, Fudge, causes trouble when the client visits, and it's implied that the agency lost the account because of this. The connection is made more direct in the TV adaptation, Superfudge.
- In Harry Potter and the Chamber of Secrets, Mr. Dursley's potential client and his wife come over to discuss a promotion over dinner. When Harry retires to his bedroom, Dobby the house elf appears and begs Harry not to return to Hogwarts. When he refuses, the house elf levitates a cake over the boss's wife's head and drops it.
- The Paul Jennings short story "Licked" (which became the basis for part of the Round the Twist episode "Little Black Balls") has this as its plotline. This time around, our narrator is the son, who is going out of his way to disgust everybody.
Live Action TV
- Heil Honey, I'm Home!, the infamous sitcom which had Adolf Hitler and Eve Braun as the main characters (seriously) used a similar set up in its opening episode. The person coming to dinner was Neville Chamberlain rather than a boss, but it's treated exactly the same way.
- Happens twice in Happy Endings, both with Jane's boss, the Car Czar. The first time, she invites him and her other male coworkers over to try and win them over, the second time, Brad foolishly invites the Car Czar over to dinner even though Jane has planned a double date for them with Penny and a new guy. The first time, it goes fairly well, the second time...not so much.
- Often happens in Three's Company.
- Happens a few times on Bewitched.
- Happens on Family Matters when Harriet's boss Nick is invited to play poker with Carl and his friends.
- Actually happens several other times throughout the series. Most straightforwardly, when Carl throws a dinner party for his boss, which is thwarted when Urkel's exploding pepper is accidentally used on the roast chicken.
- Inverted on Friends - Chandler's boss has him and Monica over to his home for dinner.
- My Family imported Susan's clueless American boss - who stayed the night and then died in the Harper couple's bed.
- Done of course on Dinosaurs:
- In 'Power Erupts', WESAYSO exec, Earl's boss Mr. Richfield invites the Sinclaire family to dinner at a fancy restaurant in order to convince Robbie to sell his volcano-powered generator designs...after WESAYSO has discredited the idea with some mass-media mudslinging.
- When Earl was made employee of the month, Mr. Richfield said he'd invite Earl and his family to dinner at his place but, since he was doing some alterations in the bathroom (or so he said), he invited himself to diner at Earl's place. With an overinflated ego, Earl had his family ready for this and even invited his mother-in-law to rub it in her face. Richfield didn't show up.
- Happened on Hi Honey, I'm Home!, Nick-at-Nite's short-lived sitcom that parodied classic shows and tropes. The boss turns out to be Mr. Mooney from The Lucy Show, played by Gale Gordon.
- Get Smart had some fun with this, as it aired during the height of the Women's Lib movement and all:
99: Max, did you say The Chief? You invited your boss for dinner tonight?!Max: What do you mean, my boss? He's your boss, too.
- The whole plot of Alan Ayckburn's How the Other Half Loves centers on two dinner visits by the same boss to his two employees on subsequent evenings - acted out simultaneously on stage.
- Not technically "the boss" as much as "coworkers", but the premise is generally the same: the song "The Room Where It Happens" in Hamilton focuses around a dinner meeting between Hamilton, Jefferson, and Madison, where Hamilton traded the location of the US capitol (Washington, DC over New York) for more financial power. One line even has Jefferson claim "I arranged the venue, the menu, the seating" (although it's unlikely that in real life, Jefferson himself would have done this).
- The The Thrilling Adventure Hour episode "Quick! Change!" has Jib Janeen stressing over dinner with his boss in a parody of Full House with Jib Janeen, his three kiddos, cool uncle Johnny, and charismatic pal Jeffy. The twist is that Jib Janeen is from Jupiter, and Jovians are natural shapeshifters and spies. In order to be considered for a plum spying account the Janeens are instructed to have the kids impersonate the parents and parents the kids while shapeshifted with red and white stripes.
- The decidedly non-creepy Lost Episode Creepypasta "Grim's Boss" centers around an unaired episode of The Grim Adventures of Billy & Mandy wherein Grim's boss, Satan (though he prefers to go by Lou), shows up for dinner and informs Grim that he's looking for an apprentice. At the end, he picks Mandy as his apprentice as he has seen no soul more evil...but Mandy has other plans and the episode ends with Mandy enslaving both Satan and Grim and basically becoming the queen of Hell.
- The Simpsons: Mr. Burns does this in "Two Cars in Every Garage and Three Eyes on Every Fish" as part of his political campaign.
- Also parodied in "The Simpsons Spinoff Showcase", where the family consists of beavers and the boss is a skunk (played by Tim Conway).
- In the episode "Twenty-Two Short Films About Springfield," there's a segment about Principal Skinner having Superintendent Chalmers over for dinner. Except Skinner's roast catches fire and he comes up with one Blatant Lie after another — from claiming the smoke is "steam from the steamed clams we're having" to passing off Krusty Burgers as "steamed hams" to saying that the fire in his kitchen is the aurora borealisnote — to avoid disappointing Chalmers.
- One more Simpsons example: In "Behind the Laughter", this was the plot of the pilot Homer shot. Bart played the boss.
- Mr. Spacely does this in the pilot episode of The Jetsons.
- Family Guy: Peter invites Mr. Weed, the owner of the toy company he works at, over for dinner. Weed chokes on a dinner roll (catapulted from Brian's mouth after Brian chokes & Peter gives him the Heimlich maneuver) and dies.
- American Dad!: Deputy Director Bullock goes to dinner at Stan's house or stays over on several occasions. President Bush even goes over for dinner one time due to Stan winning an essay after the agent that won plagarizing some of his essay.
- Rocko's Modern Life: Done in the episode "Dirty Dog", but not with any of the main characters. Instead, it played out with the parasites living on Spunky, whose lives spoofed old sitcoms.
- Mr. Slate does this a few times on The Flintstones.
- Done in the Rugrats episode "Dummi Bear Dinner Disaster," where Randy Carmicheal's boss comes over for dinner. The kids try to sabotage things when Susie becomes convinced that her dad will get a promotion and they'll have to move again if the dinner goes too well.
- Pops up in Maya & Miguel.
- Kim Possible's father has the board of directors of his lab over for dinner in one episode... right after Kim is hit by a Truth Ray that causes her to blurt out all the unflattering things her dad says about them (one has a bad hairpiece, one is a crashing bore, and one is an annoying know-it-all). Kim's dad is clearly in hot water with his bosses, until the board chairwoman arrives and turns out to be the Kidnapped Scientist Kim had rescued at the beginning of the episode. The three suck-up when the chairwoman praises the Possible family.