Pairing: Castiel/Dean Winchester
Read on AO3: http://archiveofourown.org/works/11987772/chapters/27118239
Summary: Dean’s little brother Sammy has been talking about a girl a class above him for about two weeks non-stop. 11-year-old Sam admires Claire Novak and desperately wants to be her friend, so he and Dean start planning how to make a friendship happen between them.
When Sam and Claire finally become friends, Dean coincidentally meets Claire’s big brother Castiel and falls head over heels for the gorgeous, blue-eyed boy. From that moment on, Sam and Claire are the ones helping Dean to woo Cas. The whole process naturally involves lots of pining, awkward flirting and a constantly blushing Dean.
Note: This is my first ever multi-chapter fic. I don’t really know whether to post every chapter on here or to just let you guys know whenever I add a new one on AO3. I’d be super thankful about suggestions! :)
Dean has just placed the hot bowl of spaghetti on the table when he hears his little brother closing the front-door. He and his 11-year-old brother Sammy have been living together in their own little apartment for a year. When their parents died in a car accident five years ago, they lived with their uncle Bobby until Dean’s eighteenth birthday last year. With his birthday, he finally became Sam’s legal guardian. He has worked hard to reach that point, quit school with 16 and started working as a mechanic to save money to provide a home for himself and his little brother and saved money for Sammy’s education ever since.
The last year has worked out pretty great for them and Dean is proud of how he’s able to balance being a big brother, a mom and a dad to Sam, all at the same time. He’s working at a garage from morning till late afternoon, but still manages to take care of Sam in the mornings to, pack him a snack for school, get home to cook dinner for them and spend the rest of his afternoon and evenings with Sammy. Because of his working hours, Sammy has to spend some hours at their uncle’s house every day, but both he and Bobby enjoy their time together, so Dean doesn’t feel that bad about leaving Sam with Bobby.
About two months ago he started picking up night-shifts at a bar two streets away, because it’s easy to run short on money with a kid that grows two inches every month and needs new clothes regularly. The fact that Dean would be able to sprint back home from the bar anytime Sammy needs him and it wouldn’t take longer than 6 minutes- not that he tested this theory…- doesn’t make him feel less awful about leaving his baby brother alone at night. The thing is, he really wants to be able to provide Sam everything he needs and wants, so he eventually has to stop worrying so much about him. Sam is old enough to be on his own sometimes, anyways.
Dean places two plates and cutlery on the table when Sam enters their little kitchen, a big, gummy smile plastered on his face. It’s the fifth time over the course of the last two weeks that Sammy has come home with a dreamy look and a secret smile on his face. He acts way sneakier than he has to, considering that Dean definitely knows what, or rather who, has him smiling like that. To be honest, he has already heard so many different stories about that “fierce, super cool” girl a grade above Sam and her “kind smile and courage”, that he’s a tiny bit annoyed about his brother’s admiration for her. He suspects that Sam has a tiny crush on this Claire, but every time he brings it up, Sam denies just that. Sammy says that he simply wants to befriend her because she seems like an amazing person and would surely be cool to spend time with.
To be honest, Dean is less annoyed about Sammy admiring her than about the fact that the boy doesn’t just go talk to Claire. If she’s as nice as Sammy makes him believe she is, there shouldn’t be any problem with that at all.
“Dean, can I tell you what happened today?” Sam asks, sighing happily as he plops down on a chair.
“You know I love to hear about your day, buddy! Was it Claire?” Dean winks at his blushing brother, handing him a bowl. “Grab some spaghetti before they get cold, though. I made your favorite vegetable sauce, by the way.”
The kitchen is filled with clattering until Sam’s bowl is filled up to the brim with noodles and he starts talking again.
“So, get this. Claire smiled at me today! She dropped one of her books on the way to her classroom and I picked it up to hand it back to her- and she thanked me and smiled!! And I’m sure it was directed at me, this time,” Sam beams while he rolls up some spaghetti with his fork.
“Awesome, Sammy! Did you talk to her?” Damn, Sammy’s excitement is just too cute for Dean to keep being annoyed.
“Well, not really. You know I don’t know how to start a conversation with her. She’s just so cool and she’s a year older than me, Dean! She’ll probably laugh at me…,” Sam mumbles, eyes fixed on his bowl of food.
“Come on, you told me she’s super nice and friendly! I’m sure she won’t laugh at you if you’d just try to approach her. She should be honored by you trying to be her friend,” Dean says with a serious face. “You need some help with that? You know I’d do everything for you.”
“Would you really help me? That would be so cool!” And there’s the excited puppy expression (Dean secretly loves) back on his face once again. “I mean, you have loads of experience with people. Maybe with your help we could be friends!”
That earns him a fond smile of his big brother. “Sure thing, Sammy! We can plan how we’re gonna win her over after dinner.”
On the next morning, Sam leaves home with not only one, but two slices of Dean’s homemade apple pie. The first step in their plan to approach Claire was for Sammy to offer her some of his food at lunch time. Dean hopes that she’ll accept it and they finally start talking over some food. Last night, they made a list about everything Sam knows Claire likes and decided to just go from there and hope for the best. Some small presents, nice gestures and food should probably be enough. Sammy is nice, funny and considerate Dean doesn’t doubt that Claire is going to like him a lot, as soon as she gets to know him.
If the big smile Sammy shows as soon as he enters their apartment on that evening means anything, step one seems to have worked quite well.
“We actually talked, De! It worked, you’re a genius,” Sam shouts and Dean has his arms full of his gangly, nerdy, little brother even before the latter bothered to get rid of his shoes or his raincoat.
Before he can let go of him, his puppy of a brother starts bombarding him with questions. “Okay, so what’s next? What are we gonna do tomorrow? Do you think we could actually become friends, though??”
Goddammit, Dean loves his overexcited little brother so much.
“How about we bake her some cookies?”
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