Requested by simpforsoup: Peter really wants to ask Y/N out to their upcoming prom, but Y/N is incredibly insecure and feels like she isn't pretty enough to go. Peter hates that Y/N puts herself down over every other girl and he hates that she doesn't see what he sees. One day, Y/N has had a particularly bad day, so Peter plans a surprise for her.

*Please note: as the request suggests, this one-shot contains themes of self-esteem issues. I know that this is fine for most people but it is still a trigger for some, so please don't read if you think that you'll be triggered, I'll be back soon with safe and trigger-free imagines :) Thank you and enjoy :)*

Peter's P.O.V

Peter rushed through the school corridor, his heart thumping as he ran through the crowds of other students.

"Sorry-my bad-excuse me-watch out!" he exclaimed as he ran to class. The high school prom had just been announced, an event that Peter had been waiting months for. He knew that it wasn't considered normal for a boy to be excited for the prom, but he had a plan. He had been waiting patiently for the announcement so that he could use it to ask his best friend and crush, Y/N out, and use it as their first date. He'd had the entire night planned for months, and he was on cloud nine at the thought of it finally happening. But first, he had to ask Y/N. He rushed into class, a smile immediately curling onto his lips as he saw Y/N at their usual table. He walked towards her, making the beautiful girl look up at him.

"Hey, Pete." she chuckled as he sat down next to her.

"Hey, um, you've seen the posters for prom, right?" he asked. Her smile dipped and she looked down again.

"Oh, yeah. That." she mumbled. Peter's smile also dipped, his eyebrows furrowing at her response.

"What, you're not excited to go?" he chuckled nervously.

"I'm not going full-stop, Peter." she sighed as she looked back up at him. His eyes widened, his heart plummeting to his feet. No. His plan couldn't have failed before he'd even asked her.

"What? Why not? I thought that it was every girl's dream to go to their high school prom." he scoffed. He had to convince her to go, if he couldn't, his plan was fucked.

"Look, Peter, I'm not pretty like other girls. I'm not conventionally attractive, I'm not a size zero, I'm always going to be the last one picked if I stand in a line with the other girls in our classes. If I go to prom alongside all of these beautiful girls, I'm going to look fat, I'm going to look lumpy, I'm going to look ugly. I'm definitely not about to put myself through all of that for the supposed "best night of my life" when I'm well aware that it won't be the best night of my life." she choked and shook her head as a tear rolled down her face. Peter's face softened and he looked at her as his heart shattered. Peter had known Y/N for five years now, and never had he not known her to come with some serious self-esteem issues. She had always seen herself as too fat, too ugly, too small, too lumpy, when in reality she was nothing other than absolutely beautiful. It angered Peter to know that she thought this way about herself, but not at her, at the society that made her feel this way just because she didn't look like a social media model. Peter always tried to talk her out of these mindsets and convince her that she was beautiful without accidentally revealing his true feelings for her, but that was getting harder to pull off the older that they got. And now, it felt impossible.

"Hey, no, I'm not going to sit here and listen to you say this stuff about yourself, Y/N." he shook his head as he gently took the girl's small hand into his.

"Why not? It's true, Peter. I'm not pretty enough to go, and so I won't go." she shook her head.

"Y/N, listen to me-."

"Pete, please, let's not do this here. I don't want to cry any more than I already am." she choked. Peter sighed and gave her a small smile, her returning it as he leant his hand up and gently wiped the tears from her face with his thumb.

"Okay. I'm sorry, I didn't mean to make you cry." he spoke quietly.

"It's okay, Pete. It's not your fault." she reassured. He sighed again and nodded, his gaze staying on his best friend and his mind thinking about how much he hated that she went through this as she faced the front of the class again.

Y/N's P.O.V

I lay on my side in bed, tears streaming down my face as I hugged my pillow. I'd had yet another utterly shit day at school, mainly consisting of other girls picking on me and guys telling me that I'd never be pretty enough to fuck. The worst bit was that it was all just joking and teasing to them, all of it was meaningless. But to me, every single word was another stab through my heart. I had always had issues with my appearance and those issues were only made ten times worse by the constant bullying. Peter was always there to reassure me, and I knew that the poor boy did his hardest to convince me that the bullies were wrong, but it was often a lot easier to listen to what the bullies said over what he said. Suddenly, my phone started to ring. I looked at it and sighed as it showed Peter's name and face. I pressed the green button and held the phone to my ear.

"Hey." I sniffed.

"Hey, where are you? I'm standing by your locker and I can't see you anywhere." he scoffed. I groaned quietly and squeezed my eyes shut as I realised that I'd forgotten to tell Peter that I was heading home early.

"Shit, sorry, Pete, I forgot to tell you that I'd left. I'm sorry, it's just been such an awful day. I couldn't take the insults and the comments about how ugly I am anymore." I choked and shook my head. I heard him sigh.

"It's okay, it's alright that you forgot to tell me. But listen. I have a surprise planned for you. Do you think that you'd be up for that?" he asked.

"Pete, I don't know, I just want to lie in bed and eat ice cream." I returned his sigh.

"Come on, humour me. Please." he insisted. I gulped and bit my lip, my mind starting to be taken over by the curiosity of wanting to find out what this surprise was.

"Fine, alright." I nodded.

"Brilliant, thank you. I'll be at your window in my suit at seven, okay?" he asked, making my eyebrows furrow.

"Why so late, and why in your suit?" I questioned.

"Don't worry, you'll see." he responded. I sighed and bit my lip.

"Okay, Pete. See you then." I nodded before hanging up.

I paced the floor of my room, waiting for Peter to arrive to take me to his so-called surprise. I looked down at my phone, the numbers six-fifty-nine staring back at me. As if on cue, I heard a quiet tap on my window.  I turned around and smiled as Peter was crouched on the other side of the glass with his full suit and mask on. I opened the window and looked at him.

"You ready to go?" he asked.

"You mean to see this mystery surprise? Of course." I smiled, making him laugh as I climbed out onto the fire escape. I wrapped my arms around Peter's neck and jumped, both of us knowing the drill by now as he securely wrapped his arm around my waist and I wrapped my legs around his middle. I buried my face into his neck as he extended his arm and shot his web at the next building along before flinging us into the air. My hair whipped around me wildly, my body clinging to his as he flew us above the streets of Queens. We continued to soar above the city before Peter gently landed on the top of a random building with a thud. I raised my head to look around as he softly let me go and pulled his mask off, my eyebrows furrowing.

"Pete, why did you bring me here?" I chuckled. He bit his lip and gently placed his hands on my shoulders before turning me around. My eyes widened, a quiet gasp leaving my lips. Peter had brought me here just as the sun was starting to set, our placement on the top of the building giving us the perfect view of the stunning colours that were stretching across the sky.

"Pete...it's beautiful." I whispered and shook my head, my body leaning back onto his as his hands gently rubbed up and down my arms.

"I'm glad that you said that. Because this is what I see when I look at you. What you're feeling right now, that's how you make me feel every single day. I can't stand to see you so down and upset, it breaks my heart when you say all of that horrible stuff about yourself. You're everything to me, Y/N, and it kills me to see you so upset." he admitted as he pressed his lips to my hair. I bit my lip, my eyes wavering as tears starting to roll down my face at his beyond kind words. I turned around to look at him, making him give me a small smile as I rested my hands on his chest and his arms curled around my waist.

"That's the sweetest thing that anyone has ever said to me, Pete." I whispered. He sighed as he raised his hand and gently moved a strand of hair out of my face.

"I meant every word. I just, I needed you to know how I felt. Because I really fucking like you, Y/N, and so it killed me to hear you say things like that you weren't pretty enough to go to prom. You'd be the most beautiful girl in that room." he smiled and shook his head. I returned the smile and bit my lip.

"That being said, Y/N, I'd absolutely love to take you to prom, as my date. And, well, hopefully, we can have many more dates after that." he admitted. My eyes widened slightly as I realised what Peter was asking me. My crush was asking me out.

"Okay, Pete. I'll go to prom with you. And I'll go on many more dates with you after that." I smiled. He breathed a sigh of relief, making me laugh at his reaction as he leant down and gently pressed our lips together. I returned the kiss, my hands moving up to cup his face as his hands held my waist. I broke the kiss after a moment and touched our foreheads as I looked at him.

"Thank you for this, Pete. It means a lot." I admitted quietly.

"It's okay. I'd do anything for you, especially if that "anything" is making sure that you know how beautiful and loved you are." he responded. I smiled and bit my lip, my heart filled with love as I leant up and kissed him again.