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Awkward First Sleepover

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Lots of things can happen at a Slumber Party...Wild Teen Partying, a Childish Pillow Fight or a Fanservice Faux Fight, gossiping and chit-chatting, and passing (or failing) of The Bechdel Test... and then there's this trope.
A character reveals that the slumber party she (and usually, it is she) is attending or hosting is the first sleepover she has ever been to. Usually, they happen to be at least in their early teens or even older, and are at an age where most of their peers have already been to sleepovers. This trope is used to establish them as socially awkward.
The trope is usually the result of several things: The kid whose first sleepover it is is a nerdy bookworm type, or perhaps she has overprotective parents who sheltered her from other kids to a fault. Or s/he might be perceived as a loser by the more popular crowd.
Either way, the kid whose first sleepover it is will typically feel nervous about committing a faux pas. If they are hosting the party, expect them to be overly worried about everything being perfect. If there is a person they don't know at the party, expect them to be nervous about making a good impression.
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The Wubbulous World of Dr. Seuss: In the second Seuss story in "The Cat in the Hat's First First-Day", Morton the Elephant Bird is excited but also nervous about his first sleepover at Junior Kangaroo's house. Morton finds Junior's bedtime routine strange (having Jane read to him from a mathematics book and play a lullaby on the drums) and is also afraid of the shadows that look like scary monsters. Fortunately, Junior helps Morton overcome this fear. When Morton wakes up, he freaks out when he realizes he's not in his own house, but soon remembers that he's sleeping over at Junior's house.
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Amy in The Big Bang Theory is excited to have her first slumber party at Penny's with Penny and Bernadette. She's in her thirties and Penny and Bernadette pity her as she had no friends prior to meeting her boyfriend Sheldon and his social group. She's very awkward about the whole sleepover, e.g. she thinks girl talk is talking about female anatomy, she wants to play all the games (like truth or dare) and even tries to make a pass at Penny off-screen, claiming her internet sources list lesbian experience as a vital part of sleepovers.
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A rare male example happens in Atypical; Sam has a sleepover at his friend Zahid's house in preparation for going to college (Sam is autistic and has never spent the night away from home before). The various noises and sounds in Zahid's room irritate Sam and make him leave the room, and a police officer notices Sam wandering down the sidewalk. A misunderstanding causes the officer to think Sam is on drugs, and Sam and Zahid are taken to the police station. At the station, Zahid notices the clock displaying 12:07, and he points out to Sam that Sam's managed to stay away from home past midnight.
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Big Mouth has two in the same episode that are not so much awkward as they are utterly disastrous. Complete with fist-fighting, literal sugar highs, a desperate escape from Jay's depraved older brothers and a self-aware pitbull.
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Arthur: Jenna is invited to Muffy's sleepover, and she is worried because she wets the bed.
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In The Troop, awkward geek Felix shows up in drag to crash the slumber party thrown by Hayley because there's a monster they have to hunt, but he has such a good time, and is actually accepted by the girls more in his "Felice" persona that he goes racing back to the party after they've defeated the monster.
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Bear in the Big Blue House: In "Tutter's First Big Sleepover Bash", Tutter invites his classmates from Mouse School to the Big Blue House for a sleepover. Most of his classmates have a wonderful time, but Luke is first uncomfortable with his pillow and wants to hear a lullaby. Shadow sings "Shadow's Lullaby", and even though Luke likes it, it wasn't the lullaby his parents sing to him. He ends up missing his parents and wants to go home, so Bear tells him that it's all right and he can call his parents to pick him up. The other mice overhear and ask Bear what's going on, so Bear explains the situation to them. When the other mice tell Luke that they'll miss him, Luke realizes how much his friends care about him and decides to give the sleepover another try as a result. At the end of the episode, just before the closing credits, Luke calls for Bear, telling him that he usually sleeps with a vaporizer and wants a glass of water to drink.
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In The Loud House episode "Sleepstakes," Lana is invited to a sleepover. Problem is, she's tried to go to sleepovers in the past, but has gotten too homesick and had to return home, never staying for very long. With the help of her family, she hopes to work up the courage to complete a sleepover.
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Star Trek: Lower Decks: One episode has Mariner invited to a sleepover (or "salon") by her girlfriend, Jennifer. Things get off awkwardly when she's the only one to show up in uniform, not pyjamas, and get worse when it turns out everyone else's idea of fun is boring, but Mariner remains quiet so as to not upset Jennifer. Then they get worse still when the show's A-Plot means the power's knocked out and they're stuck in the room with the oxygen quickly running out. Then Jennifer reveals she'd wanted Mariner to be her usual self and stick it to her friends.
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Gullah Gullah Island has the episode "The Big Sleepover" where both girls and boys were fighting and arguing over the space in the living room and not sharing with Binyah Binyah.
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Bob's Burgers :
In the season four episode "Slumber Party", Louise is forced into having her first sleepover by her doting mother Linda, who proceeds to invite only girls Louise can't stand. Louise manages to drive away Jodie by claiming Linda is fighting off an illness, and scares Harley and Abby off by claiming Gene has a crazy, deformed twin brother who lives in the basement, but the seemingly bland and ordinary Jessica proves to be a tougher nut to crack.
In "Cheer Up Sleepy Gene", Gene is invited to his first sleepover with Alex. Gene is already terrified of sleeping at another person's house, and things get worse when Alex decides to run away due to being unhappy with the diet his parents put him on, and makes Gene tag along with him.
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One episode of Ally McBeal sees Ally fretting over her daughter Maddie's first sleepover, owing to her own bad experiences with other girls when she was growing up.
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In the Rugrats episode "Slumber Party," Angelica sleeps over at Tommy's house for the first time. She thinks Tommy's room smells bad and opens the window, letting in a cold breeze. As a result, Tommy gets sick, and everyone ends up staying awake with him though the night as he hallucinates from his fever and eventually throws up on Angelica.
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Young Sheldon: In "A Financial Secret and Fish Sauce", Sheldon has his first sleepover, at Tam's house. He experiences several culture shocks, the biggest being the fact that the whole family shares one napkin/towel at dinner.
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Played with in the Muppet Babies (2018) episode, "Wock-A-Bye Fozzie"; Fozzie suggests having a sleepover at Miss Nanny's house when he hears about the sleepover that Summer had at Piggy's house, and Miss Nanny agrees to it. Kermit, however, is nervous about attending the sleepover, since it will have been his first time sleeping away from his parents. By the end of the episode, Kermit has a lot of fun at the sleepover, while Fozzie has a miserable time.
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In the My Little Pony: Friendship Is Magic episode "Look Before You Sleep", Rarity and Applejack have to spend the night with Twilight Sparkle due to a big rainstorm. Twilight uses this as an opportunity to hold her very first sleepover, since she never had one, and therefore is literally by-the-book as she uses a guide on slumber parties to move the plot along. The slumber party gets gradually ruined as Applejack and Rarity had been in an argument and are still mad at each other during the sleepover.
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In Cavewoman: It's a Girl's Life, Carrie decides to throw a Slumber Party for Meriem and Mona after learning that Meriem had never been to one (having spent her teen years in the jungle). Mona, who had a very sheltered upbringing, finds it quite awkward at first, as Carrie throws a slumber party that is much more 'adult' than she was expecting.
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One episode of Cold Case revolves around a first sleepover gone wrong - the newcomer was only invited so that the other girls could humiliate her, and when she wouldn't play along, one of the other girls accidentally killed her in a blind rage, afraid that she would become the new designated loser in the group.
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Party at My Index
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