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Half-Baked Niceness

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There comes the time when you are obligated to compliment a person, an object, or something else of interest. Sounds pretty straightforward. But there is just one problem. You're hitting a dilemma with the compliment; you've always been told that if you have nothing nice to say then you should say nothing at all, but in this case you're practically forced to say something even though there's nothing on your mind that would sound benign. How can you try to avoid disrespecting the item or other person?
The answer is simple: have the compliment technically qualify as one. It might not look like the most ideal or quality praise, but as long as it's meant to be nice, it surely counts right?
A character might, at one point or another, end up providing some kind of compliment (either out of necessity or their own volition), but for whatever reason, said compliment won't be what you'd normally expect; the gesture will be something bare-bones, rushed or otherwise not well put together at all, occasionally becoming rather meaningless, nonsensical, or even disrespectful or plain old descriptive of the subject of interest (such as saying "this egg is very egg-shaped" as a compliment). In short, it is bad because it shouldn't and doesn't work as an effective compliment. Naturally, this can lead to the "nice" gesture not reading as nice in spirit, only being "nice" on the technicality that the person intended it to be so.
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At the end of the Adventure Time episode "Dungeon", Princess Bubblegum tells Finn and Jake that she hopes they learned a lesson from their venture into the dungeon they were supposed to close off. They say an Aesop, but Bubblegum isn't satisfied. Finn then tries to come up with another answer and says that he learned that "[she's] a very... uh... intelligent princess" in a tone that clearly indicates even he isn't sure of his own response. Though the compliment is rushed, she readily accepts it as the answer she wanted.
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Strong Bad's Cool Game for Attractive People: During the tutorial, Strong Bad is explaining to the player that sucking up to someone is usually a good way to get them to do what you want. When demonstrating with Bubs...
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Robocop 2: Lewis notices that Robocop is behaving strangely after OCP reprogrammed him. The latter tries to make small talk and fails spectacularly:
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Rocko's Modern Life: In "Bye, Bye Birdie", Filburt has a funeral for his pet bird Turdy. Filburt asks Rocko to say a few words. As Turdy was nothing but a nuisance throughout the episode, the only nice thing Rocko has to say about him is that he was a bird. Filburt's still moved by it, though.
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In one Garfield strip, Garfield is annoyed by a heckler saying his act stinks, so he asks him if he would find something nice to say for once. For the sake of complying with his request, the heckler responds by praising the fence Garfield was performing on.
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Total Drama:
During Total Drama: "Aftermath III: Aftermath Aftermayhem", one of the challenges Beth faces is creating a haiku about Heather's positive traits. Given that Heather is a massive Alpha Bitch, all Beth can come up with at first is that Heather has ten toes.
In "Top Dog", Courtney makes Duncan sign a 32-page relationship contract forcing him to behave like her idea of the perfect boyfriend. When she reminds him that one of the stipulations is to give her a compliment once every hour, the best he can come up with is "You have...nice teeth," which isn't enough for her.
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Donnie Darko: Donnie and Gretchen are having a conversation, and the latter calls the former "weird". Donnie apologizes, thinking she was being derisive with her comment, but then she says that was a compliment.
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Steven Universe:
In "Too Far", Peridot praises Amethyst and then calls her defective, upsetting the latter. Peridot is applying her flaws in a logical context, genuinely viewing Amethyst in a positive light, but doesn't immediately realize her praise was more hurtful than she intended. To further prove she really was trying to be nice, it immediately starts bothering her once she learns what she did and later makes it clear she wasn't trying to hurt Amethyst's feelings.
In "Barn Mates", Steven tries to have Peridot "show her sweet" to Lapis, who's bitter over the latter having interrogated her for info. Peridot tries to make a card in an attempt to compliment Lapis, but the contents of said letter end up coming across as "I like you because you were of use to me".
In "Kevin Party", Kevin pushes Steven to talk to Connie after their falling out following Steven being abducted and put on trial by Homeworld Gems. Steven gets extremely nervous and messes up his opener:
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In Grease, upon entering the big dance, Frenchy asks Doody how she looks. Doody's response is that she looks like a "beautiful blonde... pineapple". Following this answer, she glances towards him as though she's wondering what it is he just said.
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Batman: Wayne Family Adventures: In "Personal Growth", Tim and Stephanie meet Damian's cheerful school friend, Skylar, and Steph puts her foot in her mouth in mentioning how not-bubbly Damian is. Trying to fix it, she claims he's great at giving compliments, mentioning one that he gave Tim. Tim is dubious, given that the compliment was that he "[has] hair."
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Little Princess: In "I Want My Snail", the Princess adopts a snail named Speedy. The offscreen voice is taken aback by the idea of a snail as a pet, which she thinks means he dislikes the snail. The voice says, "Well... he's got nice... eyes."
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Deltarune: Near the end of chapter one, Kris and Ralsei try to convince Susie to be nice towards their enemies. She doesn't get it. Ralsei tells her to try telling the enemy something that she would want someone to tell her. Susie then tries to say things like "You are unbanned from free ham sandwich day," or "Please keep tackling the soda machine." Surprisingly, it actually works, and the enemies are able to be spared. Thankfully Susie's compliments do improve.
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Regular Show: In "Pie Contest", Mordecai and Rigby get themselves into this situation by insisting on being pie judges and finding out the hard way that it's difficult and dangerous (as evidenced by Muscle Man's threats and Death showing off his scythe and a Death Glare). They don't like any of the pies but don't have the guts to tell the contestants, so they resort to giving everyone perfect scores. This severely complicates the problem where they have to announce the tiebreaker in front of everyone, which then leads to a giant pie monster's rampage. Then, once they save Pops from the monster by judging his pie and Benson prompts them to keep judging, the two try to judge Starla's pie next - they try to say something nice, but it doesn't work.
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Rugrats: In "Chuckie's Complaint", Chuckie watches an ad, in which Reptar (a Godzilla-like beast) breaks through a boy's wall and eats his cereal. He composes an angry letter to Reptar, telling him off for stealing the cereal without leaving him any. However, he then feels he needs to say something nice to make up for the complaint and adds, "Although, that was a pretty hole you left in the wall and you roared pretty good too."
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The Amazing World of Gumball:
In "The Misunderstandings," there are a few construction workers with absolutely No Social Skills whatsoever. When trying to compliment people, they just come across as creepy, like calling a lollipop "sweetie," or a cupcake "cupcake." They tell Gumball that his head is massive (their logic is that his large head means he also has a large brain and is very intelligent), and he does not take it lying down. Gumball then tries teaching the construction workers how to better compliment people, and instead, they end up flirting with him. He tells them to get out more, and the workers suggest to go to the mall. Gumball tells them not to since that's where he's going, to which they suggest schools instead. Gumball, understandably, relents and lets them go to the mall.
In "The Heart", Rocky urges his dad (Gaylord Robinson) to be positive when trying to express himself to Gumball and Darwin when the boys give him the cold shoulder. Mr. Robinson tries to do this by giving them a compliment, but because he's a Grumpy Old Man that enjoys the misery of the Wattersons and especially the kids, he ends up telling them things that accidentally come across as insults instead.
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SpongeBob SquarePants: In "Plankton Gets the Boot", SpongeBob has Plankton try to compliment Patrick so he can learn to be nicer. Plankton comes up with "Patrick, you're not a total moron. Just half of one," and when SpongeBob tells him to try again, he goes with "Your color pink is not so repugnant."
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My Little Pony: Friendship Is Magic:
In "Suited For Success", Rarity makes personalized dresses for her 5 friends. They're, however, not impressed; Applejack, Twilight, and Pinkie Pie call the dresses "something" in a rushed attempt to appeal to her, while Fluttershy just meekly calls hers "nice". Unsurprisingly, Rarity catches on very fast and they're forced to admit what they really think of them.
In "Lesson Zero", Twilight attempts to have the Cutie Mark Crusaders take an old doll she had as a filly. An old, worn, patchy doll named Smarty Pants. The girls don't really like Smarty Pants, but still try to compliment her - this results in a dull "great" to describe the doll. Of special mention is Sweetie Belle, who pauses mid-sentence just to come up with a confused response of "I really like her... mane".
In "A Canterlot Wedding", Queen Chrysalis shows up disguised as Princess Cadance and gets in on testing out Applejack's treats, much to her dismay. She takes a bite out of one of the cupcakes and evidently doesn't find them tasty, but in order to keep up the charade, she tries to appear polite and says that she "love-love-loves" them. Twilight isn't flattered by the "compliment", but Applejack fails to notice and offers "Cadance" some more cupcakes to go.
In "Ending Of The End", Cozy Glow tries to have Chrysalis and Tirek be nice to each other. Neither is keen on praising the other, but as Cozy had already tried to get them to do it before, they cut their losses and give her exactly what she wants: they use a brief description for each since they're technically not "not nice" this way.
Interestingly enough, there is an inversion in "Celestial Advice". Using a spell to share her fantasy with Spike and Celestia, Twilight imagines a potential scenario with Starlight, one where sending her to the Changeling Kingdom to study friendship goes wrong. In said scenario, a rogue Changeling turns into Starlight and harasses his fellow Changelings; one of the things he does is try to insult them, but the best he comes up with is this:
In "Equestria Games", Spike says that "[the Wonderbolts] like [Equestria] because it really has nice trees". Justified, as Spike is trying to sing the Cloudsdale Anthem but is completely unfamiliar with it, so he makes up the lyrics as he goes.
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Aladdin:
At one point, Princess Jasmine is pretending to be in love with Jafar (the main villain who wants to marry her so he can become Sultan) to trick him into thinking the wish he made with the Genie (who actually either can't or won't make people fall in love) worked. She tries to sound convincingly attracted to him, but the only compliments she can think of are "I love your eyebrows!" and "Your beard is so... twisted."
When Aladdin is trying to talk to Jasmine as Prince Ali on the balcony, he has Genie (as a bee) helping him compliment her. The latter tries to give him adjective ideas, only to blurt out "punctual" for some reason - which is what Aladdin ends up picking. Jasmine appropriately reacts with confusion, leading Genie to apologize.
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Vermintide II: Kerillian the elf has warmed to her Fire-Forged Friends since the first game, but her poor social skills and Sour Outside, Sad Inside tendencies often undermine her attempts to be personable, like when she calls Sienna the "least annoying one" as an apparently sincere compliment.
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Played with in an episode of Family Guy, where Stewie and Brian get into the shower (which traumatized the latter when he was a pup). Before they begin, Stewie... compliments Brian's penis, earnestly saying it's nice, before asking him to do the same. Brian is understandably unimpressed and doesn't respond back with a (weird) compliment of his own.
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The Electric Company (1971): There's an animated segment where a boy wants to call Miss Jones, his teacher, and wish her a happy birthday. His friend suggests singing "Happy Birthday to You" or reciting "Roses are red, violets are blue..." but he wants to tell her something different and decides to just call her up and improvise. When she answers, he sings: "Happy birthday, Miss Jones! You sure got nice... bones!"
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Star Trek: The Next Generation:
In "The Survivors", Worf tries to compliment a couple who are having Picard and his crew for tea. He is a Klingon, who are not known for being nice; he just says, in the same gruff voice he usually speaks in:
In "Schisms", Data writes poetry, but doesn't do a very good job due to using too many big words. His friend Geordi tries to find something good to say about his poems, but the only word he can use to describe any of them is "clever".
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The following is a list of statements referring to the current page from other pages.

 Half-Baked Niceness
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A Polite Index
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Character Flaw Index
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Dialogue
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Index Failure
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Half-Baked Niceness