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Playing Cupid

Summary:

In high school, Teddy begins to realize that his feelings for Phil have changed into something more intense than simple friendship. Terrified by this realization, he ends up asking Eddie for advice, the person who seems best suited to help him in this situation.

Notes:

heyyy pls read the tags!!
first time posting here im excited and i hope you like it!

Chapter Text

The hallway was full of students when Teddy felt a strong hand yank him by his shirt before he could open his locker. His back slammed against the metal as his body was turned to face Henry Bowers looking at him with the angriest loom. He wasn’t surprised at all to see the boy, he knew Henry had been after him ever since the day he didn’t let him cheat off him on the math test.

Henry Bowers, the weird punk wannabe who liked to play tough around the school and beat up students smaller and younger than him. The thing is, everyone knew that at home he was the one who got beaten and humiliated, since his father (a police officer) never treated him well. Some students (obviously the ones who didn’t get beaten by him) even think that that is a great excuse for the terrible person he had become. But Teddy never thought of him that way. To him, there is no excuse for someone to be like that, because if having a shitty father means you turn into a jerk, then Teddy would be a jerk too, and he is definitely not one.

"You better hope you don't cross my way outside, you piece of shit. Cause I'm beating the shit out of you." He snarled, grabbing Teddy by his collar.

Teddy hated how he still feared this asshole. At seventeen years old, a bully could still scare him.

“Say something, idiot!” Henry shouted, drawing even more attention from the people around them.

The look of disinterest Teddy kept on his face always seemed to fuel Henry's anger even more. But he refused to show his fear, or worse, to try and talk back to him.

Henry was about to say something else when his body suddenly got yanked back really hard. With a good 10 cm advantage in height, Phil pulled him so forcefully that Henry almost fell back on his ass.

“What the hell, dude? Leave him alone, asshole.”

Seeing Phil towering over Henry to protect him, with a look on his eyes that almost dared Henry to come closer, made Teddy feel something funny in his stomach. It was a strange, new sensation that had been visiting him lately, and it always happened around Phil.

Phil stepped in front of his friend as Henry let out an ironic laugh. Obviously he didn’t pick on anyone bigger than him, but his ego wouldn’t let him leave without a snide remark.

“He won’t protect you forever, faggot. I’ve got my eye on you.”

Before leaving, he stared at Phil for a few seconds with a cold expression, as if he actually had the courage to try to fight him.

Phil had changed a lot since they started high school. There was a time when Teddy thought the boy would just never stop getting taller, but his height had apparently settled at around 1.87 m. His dark hair no longer sat in that childhood quiff and now fell carelessly over his forehead, contrasting with his blue eyes.

Teddy had gotten taller too, but nothing compared to his friend, who was probably the tallest guy in the school. His curly hair was still cut at pretty much the same length; the difference was that his curls were no longer as perfect and neat as when his mother used to fix them every morning. Now dealing with his hair was his responsibility, and he didn’t have much patience for it, so the curls tangled more freely over his head.

He started opening his locker to grab the books for the next class when he heard Phil sighing beside him.

"Did he hurt you?"

"No, I'm fine."

"Why do you just take it, Teddy?" His tone was still a little bit angry as he leaned against the locker next to Teddy and staried at him with his arms crossed.

Teddy took a deep breath and looked at him.

"What do you expect me to do, Phil? If you're going to help me only to complain about it later then don't help at all, you don't have to."

Phil sighed again "That's not it, Teddy." His tone was gentler now. "I just think you could try and defend yourself."

“Do you think I have even the slightest chance of not getting beaten up?” Teddy rolled his eyes and slammed his locker shut, starting to walk away. He kept talking when he saw Phil following him, as always. “Do you think I want to get suspended and then still have to listen to my dad complain about it for at least an hour?”

"I'm sorry, I get it. It's just... It makes me so mad what he does do you." He ran a hand through his hair, a clear sign he was was stressed.

"It's okay, Phil. He never does anything too serious, just forget it." Teddy's tone was calmer now that he noticed Phil felt worried.

Phil sighed and draped his right arm over Teddy’s shoulders, just like he always had since they were kids and became friends at the playground. That gesture had always felt natural, but lately Teddy’s skin tingled under his touch, and he always felt his cheeks heat up as if he had a fever.

He wasn’t that stupid, he was fully aware that he was developing romantic feelings for his friend. The problem was that it terrified him completely, so he ended up stuck in a state of denial. After many sleepless nights thinking about it and many classes spent not paying attention, his mind occupied with a pair of blue eyes, he decided he would ask one of his friends for help.

⋆˚ᡣ𐭩。

It was during sociology class that Teddy decided to talk to Lilly about it. The girl was sitting at the desk in front of him with Beverly Marsh, and they were whispering something that seemed funny, judging by the way they were holding their laughter. The teacher had put a documentary on the projector and was fiddling with his folders, not even bothering to monitor the students.

At the end of the class, the students started leaving right after the teacher. Beverly stood up and gathered her notebook, waiting for Lilly to go to the cafeteria.

"Lilly!" Teddy called, still sitting at his desk.

Lilly turned around and smiled at Teddy.

“Hey, Teddy! What's up?”

“I wanted to talk to you about something, if you don’t mind.”

Lilly realized it was serious by the look on the boy’s face as he nervously fidgeted with his hands on the desk. She sat back down in her seat.

"You can go, Bev. I'll meet you later."

Beverly smiled, said goodbye to both of them, and walked out the door. Now it was just the two of them sitting at the back of the empty classroom.

“What is it, Teddy? Did something happen?” Her eyebrows knit together in a worried expression.

Teddy had no fear at all of telling Lilly. They had talked about so many things and shared so many secrets with each other. If there was anything he couldn’t talk about with Phil, he always knew he could tell her and she would patiently listen.

“I think…” He stared at the desk and had to gather the courage to speak. He didn't need courage to tell Lilly, but to say out loud the thing that kept repeating in his head, like that would suddenly make it all true. “Lilly, I think I like Phil.”

Lilly's face softened the instant she heard that and saw the fear in her friend’s eyes. Over the desk, she held both of his hands.

"Teddy, are you sure?"

In response, Teddy looked up at her and simply nodded. Lilly gave him a small, comforting smile.

“And how do you feel about that?”

“I'm terrified, Lilly. He’s my best friend. I can’t lose him.” He let out a shaky sigh.

“And why would you lose him, Teddy? He loves you. I doubt he’d abandon you for any reason.”

“I'm not so sure about that.”

Lilly rolled her eyes. “Teddy, he practically isolates himself from the rest of the school just to stay close to you, following you around. He wouldn’t do that.”

“Do you really think so?” Teddy bit his lower lip, nervous. "I'm so scared he's going to find out, Lilly!"

Lilly took a few seconds before continuing, like she was thinking about something.

“Have you ever... considered the possibility that your feelings might be mutual?”

Teddy’s eyes widened immediately, and he pulled his hands away from hers to cross his arms.

“What?! Of course not, Lilly.”

“And why not?” She frowned.

“I don’t even know if… I don’t even know if he likes… you know…”

“Boys?"

Teddy nodded.

Lilly broke into a wide smile, with the typical expression of someone who had just had a good idea. “I know someone who can help you with that.”

“Who?” Teddy asked, already afraid of the answer.

“You know the guy who’s always hanging around with your cousin? The shorter one.”

“Eddie Kaspbrak?”

“Yes! I’m sure he’ll know how to help you. After all, he’s dating that Richie guy. At least that’s what people say, but it looks like it's true to me, I don’t know.”

“Yeah, I don’t know either…”

He lied. He does know, and yes, they are dating. They’re discreet, so at school it’s just a rumor, but since Eddie is part of Stanley Uris's - his cousin - friend group, and Teddy has been to a few birthday parties with the group, he can confirm that they’re a couple, and have been for a long time.

“Thanks. I’ll think about it. You can go with Beverly. I'm done bothering you.” He forced a smile.

“Stop it, you never bother me.” She rolled her eyes with a smile. “Think about what I told you, okay? And tell me if anything happens.”

Teddy nodded. “Lilly? Don’t tell anyone, please.”

“I won't. Promise.”

She kissed Teddy on the cheek and left to catch up with her friend.

⋆˚ᡣ𐭩。

"What took you so long, dude? I was already about to leave.”

Phil was already standing with his tray in his hands, about to walk away, when Teddy arrived and sat down at the table they always shared during break.

“Sorry, I was… finishing something.”

Teddy lifted his gaze to his friend, who sat back down and placed the tray on the table again and opened the package with his snack.

“Here, I brought your favorite.”

Teddy didn’t even need to open it to know what it was, Phil almost always brought it. A sandwich with blueberry jam and the forbidden peanut butter, which his father never bought him no matter how much he asked. He looked at Phil again with a shy smile.

“Thanks, Phil."

It didn’t take long for Phil to start filling the silence by talking about the last movie he’d watched over the weekend. When they were kids, he had been obsessed with extraterrestrials and would spend whole nights drawing this crazy scenarios with all kinds of aliens. Teddy always went along with it and even helped him write stories. Over time, Phil stopped drawing those things, although he still kept most of the drawings on his wall, but his interest remained the same—now showing more through movies and books.

Teddy nodded along and gave his opinions from time to time while eating his sandwich, but out of the corner of his eye he was watching a table a little farther away.

The "Loser's Club", or at least part of them were occupying that table. Stanley Uris, his cousin who claimed to be the coolest one in the family; Richie Tozier, the geek with thick glasses and a tongue bigger than his mouth; Eddie Kaspbrak, the biology prodigy and perfectionist; and Mike Hanlon, the most normal looking one on that table, and the only one who had beat up Henry Bowers once.

The only ones not there were Beverly, cause she was probably still with Lilly, and both Bill Denbrough and Ben Hanscom.

Trying to not make it obvious he was staring, he noticed the way both Eddie e Richie looked at each other, the way they were always touching each other without even realizing it, just like magnets. They way Richie made jokes and instantly would look at Eddie to see his reaction. The way their dinamic was slightly different from the rest of the group. More intimate.

He figured it wouldn't be a bad idea to try and talk to Eddie.