Okay I know whoever requested, requested Wyatt, but I was feeling Stan today asdfgh sorry I'll do Wyatt soon
Stanley Uris, a lanky, curly-haired boy of fourteen years, was the epitome of dorky charm- in your eyes, at least. You had admired the boy for quite a while, never actually having the guts to talk to him. He just seemed too interesting to want anything to do with you. That, and the fact that you were sure his friends wouldn't like you had kept you from holding one real conversation with him.
Contrary to your beliefs, Stan wanted to talk to you. More than anything, actually. You were this quirky girl that always seemed to have something better to do than to have a conversation with him, of all people. The rest of the Loser's Club were completely fed up with how wussy Stan had been acting when it came to anything involving you, and they had been trying to push him to talk to you more and more lately.
Deciding one weekend that he couldn't take it anymore, Stan resolved that he was going to talk to you. The following Monday was a brisk March day, the whole town of Derry looking a bit greener as the very beginnings of plants began to sprout after the long, freezing winter. A smile hung on Stan's face, despite the absolute butterflies he was feeling in his stomach.
When he rounded the corner to the school, he saw you walking just in front of him. There's no better time than this, is there? Come on Stan, you got this, Stan thought to himself, trying to psych him up before he chickened out. Jogging the remaining few steps between you, Stan fell in stride next to you.
"Oh, hi Stan," you greeted, smiling widely at the boy, albeit being surprised that he had decided to walk the remainder of the way to the front doors with you.
"Uh- hi (y/n)," Stan managed to get out, while not sounding like a complete idiot. Your smile was just so radiant, he found himself not being able to form proper words.
"N-nice weather we're having," Stan said suddenly, wanting to smack himself in the face for how utterly stupid it sounded.
"Yeah, yeah it is," you said, laughing a bit. He wasn't wrong; the day looked as if the Earth itself was in a better mood than usual. You shifted the textbook you held in your arms to a more comfortable hold, trying to think of something else to say. This was it, after all, you had been wanting to talk to this boy for so long, and this was your chance. You felt like cursing yourself in this moment for being so awkward.
"okay, um, well I have to go. I'll see you later," Stan said, before taking off down the sidewalk in front of you. You called out a faint 'bye', but you knew he hadn't heard you because he was already merely a dot down the sidewalk. Shaking your head, you continued on your walk to school as if nothing happened.
Meanwhile, Stan was trying to catch his breath in front of his good friend Richie, after running for a good forty seconds, which is something he did not do. Under any circumstances.
"Yo, what's got your panties in such a twist?" Richie asked obnoxiously, and Stan rolled his eyes, despite his near-asthmatic state.
"I talked to (y/n)!" Stan announced after a minute, and Richie's mouth dropped open in shock.
"You did? what did you say?" the raven haired boy asked, leaning closer to Stan in eagerness.
"I said 'nice weather we're having'," Stan said proudly, a smirk on his face.
"...That's it?" Richie asked, all eagerness and excitement dropping from his demeanor. Stan nodded his head.
"Yeah, I, uh, kinda got scared after that and ran away," Stan admitted, causing Richie to physically cringe.
"You're seriously such a dweeb, man! God, there really is no hope for you..." Richie muttered, turning away from Stan and pinching the bridge of his nose in shame, "I'm embarrassed. You're friends with the biggest ladies man in the whole school, you should do better!"