(Dean’s is way longer because I already had it written before I decided to make this a preference. I don’t know why most of them are in grocery stores? Sorry about that. Also, I’d love to take any request you have here...)
“Dean!” you waved the candy bar around in his face, his expression dropped and he looked at you, half wondering if you were really being serious. “Please! I really want candy right now. Dean! Dean! Dean! Dean, please! I’ll love you forever.”
“Well, in that case,” he snapped sarcastically.
“Please, Dean!” you begged.
“Alright, Y.N, God! Stop with the eyes!”
“Haha! Yea!” you exclaimed, laughing as you put the candy bar on the counter, dropping a couple Reece’s cups for Dean. “Can we get coffee later, too?”
“Sure, princess.” he rolled his eyes sarcastically.
“Your sarcasm is excruciating.” You covered your heart and slipped a five dollar bill into his closed fist.
“Keep it.” he handed the bill back to you.
“You two are adorable.” the young girl behind the counter blushed, looking at you and Dean.
“Us?” you asked, peeking out from behind Dean’s arm. The girl nodded.
“Thanks.” Dean bobbed his head in the air, flipping through his wallet for a ten.
“How long have you been married?” she asked, waving your items over the scanner.
Dean looked over his shoulder at you, tucked behind him. “Five years.” he blurted.
“Sam!” you called quietly. “Sammy! Come on!” you sighed as you turned the corner and saw the tall man looking at a box of something.
“What is this?”
“I dunno. Hey, Dean said he’d rip us a pair of new ones if we didn’t get to the check out line right now.” I reported. “So we better- Are those chocolate covered strawberries?” you asked, walking slowly to Sam to look at the box he was holding.
“Guess so. You want them?”
“Uh, hell yes.”
“Will you share?”
“I bet if we both give dean the puppy dog eyes he’ll buy them for us.” you said, taking the box.
“He can’t say no to you.” Sam stated. “Not with your eyes.”
You heard snickering behind you and turned to see an old man hunched behind you. “Sorry.” he said hoarsely. “You two remind me of my wife and I when we were your age.”
“Oh, we’re not-” you started but Sam smiled softly.
“Thank you.” he beamed. “Have a nice day.”
“Ooo!” your sister squeaked. “Hello, baby sister!” you could smell the champagne on her breath when she slung her arm around your shoulder and placed a slobbery kiss on your cheek.
“I am Castiel, angel of the Lord.” Cas intorduced himself. You groaned but luckily, your sister was too drunk to comprehend what he just said.
She gasped. “Is this Cas? The Cas? The Cas you never shut about?” she laughed, waving her hand and spilling a little golden champagne on the floor. “Is he your boyfriend?” she tried whispering but it wasn’t working.
“No.” you said.
“I bet he is. You’re her boyfriend, huh?”
“Come on. Cas, you’re her boyfriend.” She nodded at the angel. He nodded. “Look,” she pointed her glass at Cas. “He says you’re together.”
“Is that how it works?” Cas asked. “I promise to watch over you, Y/N.”
aka cute shit i can imagine chuck, blair, and henry doing from gossip girl
-henry not letting anyone tie his tie’s except chuck until henry is old enough for chuck to teach him how to do it himself, but even then he still prefers chuck to do it for him
-henry and blair going to the park to feed the ducks, sometimes with dorota, sometimes just the two of them
-both chuck and blair alternating reading to henry before bed every night
-after chuck is done reading the spectator in the mornings, he gives it to henry to look at the comics and do the crossword puzzles that nate makes sure to put in every day just for him
-speaking of nate, he babysits a lot as do serena and dan
-nate takes henry to a basketball game and other sporting events
-blair, serena, and jenny putting on a pre-fashion show for henry to show off blair’s new lines for waldorf designs and getting his opinions and such
-henry modeling some of the boys clothes that blair designed which were inspired by him, even goofing around and modeling the girls clothes during the fashion shows bc fuck gender roles
-henry helping blair make her famous pumpkin pie for thanksgiving and baking holiday treats
-family trips to paris
-chuck giving henry his signature scarf which he wears everywhere but after a while he starts getting bullied for it. it starts as light teasing and shoving in the hallways at school but comes to physical fighting in the park one day and henry runs into his daddy’s arms crying and he and blair have to comfort their baby and have a menacing civilized talk with the bully’s parents
-henry scheming and bribing his way through minor situations in his life, although not nearly as bad as his parents (as stated by josh schwartz since henry would have a happy childhood and wouldn’t have the emotional instability and challenges that his parents faced)
-henry accompanying chuck on his daily walks with monkey
-henry spending the weekend at eleanor and cyrus’s or lily and william’s so chuck and blair can have some alone time if u catch my drift ;)))
-harold, roman, and blair taking henry ice skating during the winter
-chuck and blair bribing henry with cookies or ice cream or whatever to be on each of their sides when they’re betting on something or having an little argument/disagreement
-also chuck and blair making a bet on what henry’s first word will be (((they both lost)))
-yall know blair cried on henry’s first day of school and although chuck will NEVER admit it, he def got a little choked up when they dropped henry off
-blair being a boss at the school PTA meetings and taking control, planning everything from bake sale fundraisers to the schedule for snack time
-the basses having a family photoshoot every year which is displayed proudly in their townhouse like how chuck had that picture of him and blair in his penthouse at the empire (i know that was from a promo pic in real life, but it had to have been professionally done in gg world in order for it to be on chuck’s shelf so don’t tell me they wouldn’t have another photo sesh with their son)
-chuck teaching henry to play squash
-blair and henry watching all of her favorite movies together (breakfast at tiffany’s, roman holiday, etc)
-all of them matching or complimenting each other’s outfits in some way whenever they go to events/galas/charity balls together (i.e the boy’s bow ties matching blair’s dress, etc)
-when chuck is away on business and it thunderstorms at night, henry sneaks into his parents room and wakes blair up and says “i was checking to see if you needed any protection from the storm, ya know since dad’s not here” bc he doesn’t want blair to know he’s scared but henry jumps right then when thunder cracks and blair just smiles knowingly and lets him in to snuggle against her
-chuck not pressuring henry to take over bass industries or go into business and letting him know he should do whatever he wants and whatever his heart tells him to do in the future
-henry getting everything he wants for christmas and always having tons of toys unlike chuck when he was a kid fuck you bart :(((
-chuck and blair loving their baby boy more than anything in the world and always showing him the support and encouragement they didn’t receive as children
wow this turned out way longer than expected but idc i love my precious babies so much ok hope u cried as much as i did while writing this bye
“What shall we do today?” Henry asked. The two of you walked along the sidewalk, arms linked.
“I’m going on an adventure!” you pumped your fist in the air.
“No, no, Y/N, the adventures enjoy are usually of the literary nature.” he shook his head seriously, looking down at you.
“No, Henry, I was making a reference to The Hobbit.”
“Never mind. Let’s… go in here!” You yanked his arm and he fell in the door after you, laughing nervously as a few people stared and he straightened.
“Y/N…” he stood straight and pulled at the tail of his suit jacket. You rolled your eyes.
“Henry,” you mocked.
“Such a lovely couple. Can I help the two of you?” A worker greeted, smiling.
“Thank you,” you smiled. “We’re looking for The Hobbit.” you told her. She directed you to the book, complementing you again on what ‘a lovely couple the two of you make.’
“Y/N,” Henry blushed. “I-I know I’m somewhat ignorant when it comes to relationships in your time but… are we in one?”
“Are you serious?”
“I… I just… Dean has been telling me things about you, pointing out things I don’t think I’d have noticed or given a second thought if he hadn’t made them known to me.”
“Yes.” he nodded. You stepped closer to him, sliding your hands up his chest and around his neck. You got close to him, close enough that his warm breath fell onto your nose and you moved your lips close to his.
“Y-Yes?” he stuttered quietly, turning red.
“Don’t take advice from Dean.” you whispered in his ear before you turned and took off running down the isle, leaving a flustered Winchester behind you.
“Y/N!” Chuck stressed. “I can’t do this…” he shook his head. “I can’t. They don’t want to hear what I have to say. They’re going to throw tomatoes at me or something.”
“Where would they even get tomatoes, Chuck? Come on! They wouldn’t be here if they didn’t care about what you have to say. Just go out and be yourself.” you smile, rubbing his arm.
“Come with me.”
“I can’t do it unless you go with me! Please, Y/N!” Chuck begged.
“And now, without further a due, Carver Edlund!” the announcer introduced. You pushed him onto the stage before he could protest only to have him walk right up to the microphone and call you onto the stage.
“This person has been a huge source of inspiration for me. They’ve picked me up off the floor, literally, many a time. So come on out here, Y/N.” Chuck held his hand out for you as a stagehand brought you a chair to sit in near Chuck and a microphone. The small crowd clapped.
“Questions?” Chuck asked. One small young woman in the front row jumped out of her seat, waving her hand in the air. “You,” he pointed her out.
“You and Y/N are so cute! I can’t even!” she squealed.
“That wasn’t a question… but thank you…” Chuck said.
“So you are a couple?!” she asked urgently. Everyone in the room leaned forward, anticipating the answer. You saw the small glint in Chuck’s eye as he watched the crowd watch him.
“Yes!” you blurted out before Chuck refused the girl. Chuck looked at you, shocked and smiling a little.
“What’s that like?” the girl asked you.
“It’s amazing, he’s a genius. He’s kind and sweet and smart and just… the best person I’ve ever met. He’s my best friend. I love him a lot.” The whole crowd sighed a collective ‘awwwwwwwwww’ and Chuck stared at you still. You grabbed his hand and pulled it into your lap.