Teenage Love Story, Part One- S.M.
Pairing: Shawn Mendes X Reader
Prompt: The summer of 2015 was the summer that you spent with your sister, Taylor Swift, on her 1989 World Tour. It happened to also be the summer that you fell for the shy new singer Shawn Mendes.
Word Count: 4100
Featured Song: Wake Me by Bleachers
Previous Parts: Teaser
~~~
June 2015
“Y/N, you’re here!” You were caught off guard when you were suddenly enveloped in a large hug from your older sister.
“Hey, Taylor.” You smiled, hugging her back tightly. She pulled away from you and you admired her tour outfit consisting of a black top and a colorful skirt. “I love the look.”
“Thank you. It’s very shiny.” She replied, doing a small spin. “I can’t believe you’re really here for the summer.”
“I know, it’s going to be the best summer ever.” You were happy for your sister, and you were even happier that you were able to join her for a few legs of her 1989 tour while you were on summer break from school.
“I have to go because I’m due on stage soon, but I’ll see you afterwards. Pittsburgh’s going to be incredible.” She hugged you one last time before rushing off through the backstage.
“You’re really pushing it with a delayed flight.” Your mom teased you.
“I know, I know. Who knew Nashville to Pittsburgh would be so troublesome?” You laughed. The two of you began to head off towards your special viewing area in the crowd. Turning a sharp corner backstage, you were suddenly hit by another body, making you tumble to the ground.
“Whoa, I’m so sorry.” The person said, holding out a hand to help you.
“It’s alright.” You replied, looking up at them as you took their hand. You quickly recognized the face of Shawn Mendes, the new singer that was Taylor’s opening act. He seemed to freeze once he had helped you up.
“Thank you.” You said, smiling at him softly. He went to say something in a reply, but then nervously turned and scuttled away. You looked at your mom with a raised eyebrow, “Did I do something wrong?”
“He’s shy.” She stated. “If there’s one thing I’ve noticed about him over the past few weeks, he doesn’t do much talking to pretty girls his age.”
“Wait, he’s-”
“Sixteen. He’s got talent.”
“Wow, that’s impressive.” You let out a small laugh. As you and your mom continued your way through the stadium, you couldn’t help but think of the young star that you now so desperately wanted to talk to.
~~~
“So,” Taylor said, sitting beside you backstage a week later. Everyone was gathered around the large open room, talking amongst each other. Your eyes landed on Shawn, who sat by himself in a corner softly playing his guitar.
“So?” You raised an eyebrow at her, wondering what she was on about.
“You know, Shawn’s kinda cute, isn’t he?” She playfully nudged your shoulder, following your eyes over to him. He looked up and, upon seeing you and Taylor looking over at him, he quickly ducked his head down and returned to his guitar.
“Mom said he’s shy.” You teased.
“Yeah, I heard you had a literal run-in with him the other day.” She said, “You should go talk to him. I know he’s single.”
“Taylor, you did not seriously invite me on this tour just to play matchmaker, did you?” You asked with a small laugh.
“I’ll never confess.” She stood up from the couch, “He’s not coming with us to Europe so you won’t see him again until July.”
“You’re unbelievable.” You said as she walked away to talk to one of her dancers. You looked back over at Shawn and sighed. You stood from your spot and walked over to him. His fingers stopped playing his guitar when you sat beside him.
“What are you playing?” You asked him, a smile forming on your lips.
“Just a song I’m writing.” Shawn replied.
“What’s it called?”
“There’s Nothing Holding Me Back.” He said. He turned back to the guitar and began to strum the notes of the song. When he stopped, he looked back up at you sheepishly, “It’s not finished yet.”
“I’m sure with lyrics it’d sound pretty great.” You teased.
“I’m still working on those too.”
“So, why are you over here by yourself? Everyone’s socializing and you’re literally in a corner.” You asked with a playful tone.
“I just, I get nervous because everyone’s so much older than me and much more experienced.”
“Hey, that’s what I’m here for. Us teenagers have to stick together, right?” You nudged his elbow with yours.
“How long-” He cleared his throat as his voice cracked a bit, making him blush nervously, “How long are you here for?”
“I think I leave when we’re in Canada, like Edmonton or something.” You said.
“You know, I’m, um, I’m from Canada actually.” He said.
“Really? I’ve never actually been.” You replied.
“Well, I live near Toronto. It’s on the other side, but if you’re ever in Toronto, I could give you a tour, or something.” Shawn trailed off at the last part.
“I’ll let you know if I ever make it to Toronto.”
“That’s cool.” He paused and you could tell that everyone was getting ready for the concert. The fans were beginning to enter the arena, it was just about time. Shawn bit his lip nervously, searching for something else to say.
“Do you want to exchange numbers? I’ll need someone to talk to when I’m in Europe, and, who knows, I might end up in Toronto at some point.” You smiled as he rushed to get out his phone. It took a week and you definitely liked the awkward boy in front of you.
~~~
“Are you sure you have everything?” Your mom asked for what seemed like the millionth time.
“Yes, it’s just a few days, mom.” You reassured her, holding onto your suitcase and purse. After texting and sometimes calling him throughout the entire European leg, you were going to visit Shawn for a few days following the Montreal show. Taylor had a few days off and Shawn would be opening for her again in East Rutherford, so you had planned on seeing him for the few days you were off before returning to the tour.
“You’re making her worry.” Taylor said, coming up to you and giving you a hug.
“Oh please, this is nothing compared to you at sixteen.” You teased.
“Have fun, and don’t do anything I wouldn’t do.” She replied.
“Y/N, are you sure you’re okay going alone?” Your mom asked- it was another question she had repeated to you over the past few weeks of planning this small trip.
“Yes, Shawn’s just going to show me around Toronto. I’ll even call you all two and a half days that I’m gone.” You answered.
“Say hi to Shawn for me.” Taylor told you as your mom hugged you one last time.
“I’ll see you in a few days.” You smiled, waving goodbye before getting in the car to take you to the airport. You really liked Shawn, and you could only hope that he somehow felt the same, so you were looking forward to this trip.
When you got off the plane in Toronto, you followed the signs for the exit. You smiled upon seeing Shawn waiting for you near the baggage claim.
“You made it.” He smiled, giving you a tight hug. You were surprised by the embrace, it was the first time he had hugged you, but you leaned into it.
“Just about killed my mom to let me leave, but yeah I’m here.” You said.
“Let me grab your stuff.” Shawn stated, reaching for your suitcase.
“Shawn, I got it-” You stopped yourself short as he took the suitcase from you anyway.
“Let me be a gentleman and carry it.” He teased. He led you out to the parking lot and came to a stop by a mini van.
“Is this your ride?” You teased while he unlocked the car.
“Technically it’s my mom’s.” Shawn replied, placing your stuff in the trunk.
“Thank you for picking me up.” You told him as the two of you entered the car.
“No problem, I’m still trying to think of what to show you exactly. Toronto’s got a lot to see and we only have a couple of days.” He said, starting the car and pulling out of the parking lot.
“I’ll be happy with anything. It’s better than figuring out something to do in New York City.”
“Is that where Taylor’s off to?”
“Yep, back to her place in the big apple.” You paused for a moment. “So, what’s your family like?” From your spot in the passenger seat, you admired Shawn while he spoke about his family, his eyes lighting up as he recalled details about them.
“I was thinking we could just hang around Pickering today. There’s this place that has the best coffee ever.” Shawn said as he pulled the car into his driveway.
“Sounds amazing.” You replied. Shawn turned off the car and the two of you got out. He rushed to the trunk to get your suitcase out before you even had to opportunity to try.
“Your family’s going to think I’m so pathetic for not carrying my own luggage.” You teased.
“They’re going to love you. Come on.” Shawn used his free hand to grab yours, leading you into the house. He still held onto your hand as he called out for his family.
“This must be Y/N.” Manny smiled, coming into the entryway to greet you.
“We’ve heard so much about you.” Karen said kindly.
“Mom,” Shawn warned with a blush on his cheeks, quickly dropping your hand when he noticed he’d kept hold of you.
“Well, it’s not a lie.” Aaliyah stated, coming into the room.
“So, Y/N, this is my dad, Manny, and my mom, Karen. And this is my little sister, Aaliyah.” Shawn smiled, introducing you around to everyone.
“It’s so nice to meet all of you.” You replied.
“Shawn really has told us a lot about you, by the way.” Aaliyah said teasingly, making you laugh much to Shawn’s dismay.
“Anyway, I’m going to show Y/N the guest room.” Shawn stated, ignoring his sister’s comment. He led you down the hall.
“So that’s my room,” He pointed to one of the open doors. He quickly shut the door, not before you saw the clothes strewn out all over his floor. “Sorry, I’m packing.”
“It’s fine. I’d be surprised if you had a clean room.” You joked as he playfully rolled his eyes at you.
“And here’s the bathroom, and then the guest room.” Shawn said, showing you into the bedroom. He set your suitcase down by the dresser before smiling over at you.
“Can I change before we leave? I kinda don’t want to wear airplane clothes all day.” You admitted sheepishly.
“Oh, yeah, I’ll be in the kitchen.” He replied, closing the door as he left the room. You smiled to yourself as you changed into another outfit. Making your way to the kitchen, you heard Shawn talking to his mom about you.
“She’s incredible, isn’t she?” Shawn said. You stopped in the doorway as he spoke, his back turned to you. He went to take a drink of his water when his mom spoke up.
“I’d say she’s girlfriend material.” Karen stated, making Shawn choke on his water. As he turned around to cough, he realized you were standing there. He turned beet red as soon as he saw you.
“I’m ready to go.” You said, letting out a small laugh at his actions.
“Right. Coffee.” Shawn nodded, setting down his cup. He waved goodbye to his mom and rushed you out of the house awkwardly.
“I don’t know how I’m ever going to step foot in there again.” He said, starting up his car.
“It’s okay, Shawn,” You laughed, placing a hand on his bicep, “I’d say you’re boyfriend material.”
You couldn’t stop yourself from giggling at him blushing from your words.
As Shawn showed you around Pickering, you found yourself fully enjoying yourself, wanting nothing more than to just be with him. It all felt so sudden, but you were so sure about him. At the end of the day, he was driving you back to his place, the radio playing faintly in the background as you took in your surroundings.
“I love this song.” You smiled, turning up the radio as you heard the familiar tune of Wake Me by Bleachers.
“I’ve never heard this song.” Shawn let out a laugh at your reaction.
“It’s the best driving song. Can you open the sunroof?” You asked. He nodded and clicked the button to have it open. You sang along to the song, in pure bliss. As the bridge came up, you stood up through the sunroof, much to Shawn’s dismay.
“Hey, Y/N, that’s not safe.” He said, worried.
“If you’re lonely, lonely, lonely, wake me,” You screamed the lyrics out passionately into the night, ignoring his calls. The bridge ended and you sat back down. Shawn immediately closed the sunroof.
“I didn’t know you could sing.”
“Did I disappoint you for actually hitting the notes?”
“You’re something else, aren’t you?” He smiled over at you.
“And you’re cute when you’re worried.” You teased. He blushed again, taking a moment to come up with a response.
“And you’re cute all the time.”
“Aw, look at you flirting back.” You joked, “I’m so proud.”
“You’re definitely changing me, that’s for sure.” He pulled into his driveway and looked over at you with pure admiration in his eyes. The moment was cut short as Aaliyah came outside, beckoning the two of you inside.
The next day went by smoothly with the two of you exploring Toronto, and Shawn even took you to a Raptors game. You were enamored by the way he got so into the game. He even went as far as explaining the game of hockey to you; you didn’t have the heart to tell him that you had actually seen many hockey games before. The last day, his mom scolded him for not being done with packing, which led to you lounging on his twin bed while he packed.
“I’m sorry your last day is spent like this.” Shawn said, sheepishly. “I swear I was almost packed a few days ago.”
“Shawn, it’s fine. It’s fun watching you try to sneakily smell your shirts before deciding if they go in the laundry or not.” You laughed, and he immediately flushed.
“I’m messy.”
“It was cute.” You replied. He smiled at you before quickly turning back to his suitcases. Your eyes drifted over to the few guitars he had out, leaning up against his wall. “Can I play one of your guitars?”
“You play?” He looked back at you with a surprised look on his face. His expression changed to fondness before handing you one of his guitars, “Here, use this one. It’s my favorite.”
“It’s lovely.” You said, gently taking the guitar from his hands. You started to strum random notes as he went back to packing. “Okay, guess the song.”
“Alright.” He laughed, listening as you began to play the guitar. His laughter continued as he recognized the song, “Imagination by that one super annoying kid.”
“Yeah, that one kid with the squeakiest pre-puberty voice.” You teased.
“Hey, I have-” Shawn stopped himself out of embarrassment.
“You know, Imagination is the first song I ever heard of yours.” You stated, bringing him out of his worries.
“Really?” He sat beside you on the bed while you kept playing the notes softly.
“It’s probably my favorite song. It’s sweet and innocent, and everything a love song needs.”
“You actually like it?” He looked surprised by your confession.
“Well, maybe There’s Nothing Holding Me Back will change my mind.” You smiled.
“Oh, I finished it. Do you want to hear it?” Shawn asked.
“Of course.” You handed him the guitar and he took it before playing the familiar notes. You watched him get lost in the moment as he sang the lyrics; you’d never seen him look so comfortable. He finished the song and looked over at you, anxiously awaiting your response. “I love it, but it doesn’t beat Imagination quite yet.”
“If you love it, then it’s good enough for my next album.”
“Your next album?” You raised your eyebrows at him, leaning in closer to him. “Guess I’ll be first in line to buy it.” Shawn leaned in closer to you, his eyes ducking down to look at your lips. You felt yourself falling closer to him when there was a sudden knock at his bedroom door.
“Oh, was I interrupting?” Aaliyah asked, biting her lip to hold back a laugh. Shawn sighed and moved away from you to glare at his sister.
“What do you want, Aaliyah?”
“Mom wanted to know how packing was going. I’ll let her know you’re preoccupied.” She bounded off down the hall despite Shawn’s calls. He nervously looked back over at you and found relief when you were blushing just as hard as he was.
“She kinda ruined it, didn’t she?” He asked sheepishly.
“Kinda.” You laughed. You could tell Shawn was attempting to work up the courage to try again when his sister came back into the room.
“Dinner’s ready.” She stated, ignoring Shawn’s death stare. He coughed awkwardly before getting up from his bed and setting his guitar down. You followed him out of the room to the dining table, where Karen and Manny were waiting.
“So, packing,” Aaliyah started, raising her eyebrows at Shawn accusingly. You let out a giggle as his blush was still very apparent.
“Yeah, I’m packing.”
“Looked like you were close to kissing Y/N.” She teased, making Shawn and her parents call out her name as a warning.
“Mom, can you make her stop?” Shawn asked, pointing to his younger sister.
“Shawn, you can’t really be that surprised. Y/N’s the first girl you’ve ever brought home, first girl you’ve even talked about.” Karen said, making you hold back a laugh.
“I’m so sorry for my family.” He stated, turning to you.
“You’ve met mine, it’s much worse.” You laughed, “Actually, you haven’t met Austin yet, have you?”
“Who’s Austin?” Manny asked.
“My older brother.” You replied. The sarcastic smile on your face told his family enough of why it was a rather good thing for Shawn to have not met him yet.
When you and Shawn returned to Taylor’s tour in East Rutherford the next day, you felt uneasy about your friendship with him. Though you’d only known each other for a short period of time, he was someone that you cherished and, ever since his room last night, you were unsure of where that left you two. It was clear that he returned the feelings, but, while getting back to the reality of the tour, you just didn’t know what to think anymore.
“I missed you.” Taylor smiled, pulling you in for a hug the second you arrived to the arena. Shawn was instantly taken away to rehearse for tonight, leaving you basically alone with your sister.
“I saw you like three days ago.” You teased.
“I can still miss you.” She replied, “What, did you not miss me?”
“Of course, I missed you.”
“Okay, I want to hear everything. Did he kiss you?” Taylor asked, a glimmer of hope in her eyes.
“Oh my god, no!” You exclaimed, embarrassed.
“So close, damn.” She shook her head at you. “Did he at least try?” You playfully shrugged your shoulders with a small smile on your face, and her eyes lit up in excitement, “Aw, he did!”
“Well, he tried twice, but his sister kept interrupting.” You stated, “But, come on, Tay, I’m not going to kiss and tell.”
“You didn’t kiss yet so,” She trailed off at the end. “Come help me pick out my outfit for tonight.” She grabbed your hands and whisked you off to her dressing room. You laughed at her lightheartedness, knowing she was just going to push you even more towards Shawn.
“Which skirt?” She held up two of her entrance skirts, one purple and one blue.
“I think blue tonight.” You said, and she nodded approvingly.
“So, I was thinking that you should ask Shawn out during my show because we both know that boy won’t do it on his own.”
“Taylor, I came to help you with fashion decisions.”
“You should know by now that that only means I’m pressuring you even more into dating Shawn.” She shrugged teasingly, sending a wink your way.
“I’ll think about it.” You told her as she went behind her curtain to change into the outfit.
“Your loss.” She stated as if it was a simple fact. You let out a small sigh, trying to decide what to do that night.
Later that night, Shawn had gotten off of the stage and Vance was now up there. Taylor was gone ‘preparing’ and so that left you with Shawn. You began to question if this was even a good idea, if he’d even say yes. You knocked nervously on Shawn’s dressing room door.
“Yeah?” He answered the door casually but then immediately stood up straighter when he realized it was you. The small change made you blush. “Oh, hi, Y/N. What’s up?”
“I was wondering if you wanted to, um, to go out and get something to eat? I’m kind of over the catered food here.” You asked. Before he replied, he blinked a few times as if trying to process that this was reality, that you were in front of him asking him out.
“Y-yeah, I’d love to. Let me grab a jacket.” He said, before shutting the door and disappearing into the room. You swore you heard a shout followed by a crash and then a swear. You were about to knock and ask if everything was okay, when he opened up the door again.
“Ready?” You asked.
“Ready.” He nodded, almost breathlessly. As you two walked down the hallways of the arena, you heard the audience grow louder, signaling that your sister had just made her way onto the stage.
“Where are we going?” Shawn asked, following you to one of the cars.
“There’s this ice cream place that’s supposed to be really good. I thought maybe we could go there.” You offered. “Is that okay?”
“That sounds great.” He replied. A member of Taylor’s security team drove you two over to the shop and kept a safe distance from the two of you. With Taylor headlining the world’s biggest tour at the moment and Shawn’s career increasing every day, security was a necessity.
“I watched your performance. You were really good.” You told him as the two of you sat down with your ice cream cones.
“Thank you. I feel more confident every time I’m up there.” Shawn said, “Taylor’s been an incredible help with everything.”
“I got lucky. She’s the best sister in the world.”
“She’s done so much for me, and she introduced me to you.” He stated, nervously scratching the back of his neck.
“Correction, you ran into me.” You teased, making him laugh, “And then I had to go talk to you first.”
“Okay, well, if it wasn’t for her, then we still wouldn’t have met.” He tried to reason with you.
“I guess you got me there.” You shrugged playfully.
The rest of the night went on with conversations being made between the two of you. When you arrived back to the arena, it was during Taylor’s encore. As the two of you walked around the halls, you noticed his hand kept brushing against yours. You were just about to confront him about it when he finally just grabbed your hand in his.
“Finally.” You let out a small laugh.
“Was that too much?” Shawn asked, ready to pull his hand away.
“No, I was just wondering how long it’d take you to finally hold my hand.” You teased him.
“Oh, so this is okay?”
“Yes, this is more than okay.” You replied, “So, since I planned the first date, does this mean you’re planning the second date?” He looked at you with a happy, yet surprised look on his face.
“Yeah, I can plan that.” Shawn smiled.
“Good, I can’t wait.” You leaned in and gave him a soft kiss on the cheek. As he stood there, flustered by your actions, Taylor came off the stage, cueing you it was time to head to the hotel.
“I’ll see you tomorrow.” You leaned in and kissed his cheek.
“See you tomorrow.” He replied, letting go of your hand as you walked away to your sister.
“Did he kiss you yet?” She teased quietly.
Part Two Part Three Part Four Part Five
~~~
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