a/n — this one is long to make up for the last short gilbert imagine i wrote :)
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it's friday night, and y/n was at a party. at billy andrews' house. why she was there, she didn't exactly know. it might've been because gilbert went.anyways, billy andrews wasn't close with y/n, but his sisters are, and they made him invite her. she didn't quite want to go, but all the girls made her. sadly, anne wasn't invited, and y/n planned on scolding billy about that.
but for the time being, she tried to have fun.
diana and ruby made her sit by them, while josie pye flirted with billy. ruby glanced at gilbert every few seconds, and y/n tried not to notice.
y/n had a crush on gilbert for about two weeks, and she wasn't planning on anyone knowing. it was a crush, it didn't matter...
the party was fun so far. everyone had a nice dinner, and y/n thought she noticed gilbert glance at her a few times. probably just hopeful thinking, she thought sadly.
everything went without a hitch... up until the prank.
"alright everyone, let's go outside," billy and josie suggested.
"but it's dark out," gilbert protested. y/n nodded.
"that'll make it more fun," billy coaxed.
"make what more fun?" y/n asked. she was not up for billy's games tonight.
"oh nothing...let's go!" josie exclaimed, and everyone grabbed their coats and hats.
y/n groaned, but she followed the crowd. bad idea on her part.
billy led the group deep into the woods, and stopped. "alright, now this is hide and seek, but with blindfolds. we put the blindfolds on two people, spin them around, and hide," billy explained to the confused group.
"why do we have to spin them?" ruby asked.
"just to...make the game more fun," billy said, eyeing josie. she nodded.
"okay, i think... gilbert and y/n should be blindfolded," josie said slyly. y/n looked at her.
"um, no thanks," she said rather loud. diana grabbed y/n's hand.
"don't worry, it'll be fun," she whispered.
"i'll do it," gilbert said. "only if you do it, y/n." y/n looked at him.
"fine," she grumbled. gilbert smiled.
"there we go!" josie exclaimed all too happy. she took out the blindfolds and handed one to billy. then they tied the blindfolds around y/n and gilbert's eyes, and spun them around.
little did y/n know, they weren't planning on hiding. they were planning on leaving the two in the woods. everyone knows they both have a crush on each other, so billy thought it would be funny to prank them.
then everyone ran off while y/n counted to 30. when she took the blindfold off, there was no sign of anyone.
"let's go look for them," gilbert said and offered her his hand. she slowly took it.
the two of them started looking around. they looked behind trees and rocks, they looked everywhere. but they found no one.
"i don't think they're here," y/n whispered. gilbert nodded.
"billy probably thought it'd be funny to leave us out here," gilbert growled.
"why?"
"i...don't know. let's just go back," gilbert replied.
the two of them started walking, but quickly realized they were going the wrong way. they tried to correct themselves, but they didn't know which path was the right one.
"i think we're lost," y/n sighed.
"yeah. let's just stay here until someone comes to find us. billy's parents are bound to figure out we aren't there," gilbert explained, and they sat against a tree and waited.
it was beginning to get very cold out, despite both of them having a coat. after a few hours of talking, y/n started to shiver.
"hey, are you cold?" gilbert asked her. she shook her head.
"i'm fine, don't worry about me," she replied. she looked at the ground. does he care for me?
"well i don't think you're fine," gilbert said, and threw his arm around her. he pulled her close and started rubbing her coat, trying to warm her up.
"thanks." y/n looked up at him and smiled, and he returned it. then he hesitated, and slowly reached for her hand. she noticed, and slipped her hand in his.
"y'know, y/n, i do like you. that's probably why billy and josie made us get stuck out here. i understand if you don't feel the same," gilbert confesses to her. she just stared wide eyed.
"gilbert, i do like you... a lot. but of course i never said anything cuz ruby called dibs and such," she replied. she made quotation marks when she said the words 'ruby called dibs'. gilbert laughed. it was an amazing laugh, in y/n's opinion.
"that's not a good reason," he mused. she rolled her eyes.
"i know, but josie would hate me—" y/n was cut off but the loud neighing of a horse. they were coming for them! she hasn't realized the sun started to come up. they've been sitting out there for hours, and y/n felt as if she was a twig, ready to break.
gilbert noticed her fatigue and helped pick her up. "i've got you," he whispered, then slowly kissed her forehead. she blushed as he tilted her chin up, and she met his eyes. he was significantly taller than her.
"can i...kiss you?" gilbert asked hesitantly. she nodded. then their lips met, and y/n melted into his arms. it was the perfect kiss.
just as they broke apart, someone on a horse came for them. it was matthew cuthbert. they must've held a search party or something.
"found you two," he muttered with a smile. then the two kids in love jumped on the horse with him, y/n sleeping on gilbert's chest the whole way.

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'anne with an e' imagines and preferences
Fanfictioni wrote this in middle school so please don't hate😭 these are 'anne with an e' imagines and preferences. includes gilbert, jerry, billy, and charlie!! i do preferences (& requests) for cole too!! REQUESTS CLOSED!! *i will have typos, just bear with...