Summary: 4 times Tyler tried to use pick up lines to win Y/N's heart, and then the one time he just asked her out
Requested: Yes
It was halloween, The best time of year in Tyler's opinion. When he was younger, he loved it because it gave him the chance to see girl half naked without doing much work- he was a boob guy, what can he say? It was also his favourite time of year because of the weather, there was nothing like taking a walk with the dogs and smelling the familiar burning of a campfire or feeling the crunch of leaves beneath his feet. October always brought great memories, like the time he went trick or treating with his sisters and they got large candy bars at a house down the road from their own, or like the time he scored his first hockey goal.
Fall was an amazing time of year, and because Halloween was so important to him, Tyler found himself throwing the biggest party of the season. Other than playoffs of course.
His house was filled to the brim with people, some of them he didn't know, but the rest were teammates and friend's everyone accompanied by a date. He was dressed as Mario, a costume he had put together with Jamie and one of the other guys. They bought these tiny toy cars and attached balloons to them, driving around the house and showing off for their guests. The three of them were Mario, Luigi and Yoshi. A Nintendo dream.
Making his way towards the living room, Tyler parked by the couch, he was in front of Y/N, a friend of the team. Tyler couldn't remember who she was friends with, but the first time he had met her- they had been going to Disneyland, it was during the offseason and everyone had planned this trip months ago. One of the guys was going to bring their girlfriend, but they ended up splitting so Y/N was given the ticket.
There was an odd number of people in their group for the rides so Tyler took it upon himself to hang back and go on the rides with Y/N so she wouldn't be by herself. They found themselves getting along swimmingly, it was nice- even though one of Tyler's friends was bummed about not having their girlfriend around, it turned into a good situation for the hockey player and Y/N to become friends.
Friends, because Tyler hadn't been the best at flirting back then. They were standing in line waiting to ride the teacups when Tyler decided to be cheeky. "Theres something wrong with my phone, It doesn't have your number in it." He grinned at the girl. The sun was beating down at them and as he waved his phone in front of Y/N's face, he didn't realize that she hadn't been listening to him.
"Maybe the heat did something to it." She hummed, holding her hand in front of her face to block the sun. She had a dopey grin upon her face. Even if she hadn't noticed, Tyler's ego was still a little wounded. He let it go though and spent the rest of the day hanging out with his new friend, she was amazing to be around.
Ever since then, Y/N had been showing up to more and more events, she was often found at brunches with the WAGs or attending games in the box, she had even earned herself a key to Tyler's house whenever she wanted to come over.
Looking down at the three boys as they parked in the living room, Y/N laughed softly. "You know- you might end up getting a parking ticket, I think someone is dressed as a sexy cop around here." She winked at them, taking a sip from the beer in her red solo cup.
The woman was wearing a football player's costume. Just a cheap thing she picked up from the local halloween store. She had a jersey style dress on and white tennis shoes, black strips painted under her eyes and a number 10 on the front of her shirt. She was cute, not over doing it like some, but still incredibly sexy in Tyler's eyes.
Over the course of their friendship, he had developed feelings for her- they were mutual but Y/N was so oblivious to how Tyler felt that she never acted on her own.
Letting out a low whistle, Tyler had her do a spin- the girl laughing softly. Maybe tonight would be the night that he finally made a move on her. Deciding to test his luck, The man grinned.
He wrapped his arm around her and whispered in her ear. "Are you from Tennessee? Cause you're the only ten I see." He thought it was cute, she had a ten on her dress, it wasn't sexual, and it was the perfect amount of flirty.
It seemed like Y/N didn't find it as flirty as he had hoped, instead she just tossed her head back with a laugh and took another drink. "God Tyler- Sometimes I don't know what's going through your head." She fluffed his hair before walking off with one of the girls, leaving Jamie to clasp Tyler on the back.
"That was painful." Chubby chuckled.
Tyler just clenched his eyes shut and nodded slightly. "I know."
If there was one thing about Tyler, It was that he was persistent. He had already struck out twice with hitting on Y/N but like they say. 'Third times the charm' They were at a bar just for a night out after a string of bad games, the Dallas stars were on a losing streak and Captain Jamie Benn had dictated that everyone needed a night out in order to destress.
So the green and white took off to their usual spot, a bar in downtown Dallas that had an array of games as well. They had everything from pool, to ping pong.
No matter how bad the Dallas stars had been playing lately, Tyler was determined to Make one thing go right for him that night. He was gonna finally get the girl. Y/N had tagged along with him in his truck but quickly found her way to the other girls. She didn't abandon him by any means, but it wasn't her plan to hang off him all night while he talked with the guys.
As she talked about work with Katie and some of the other girls, Tyler was watching from afar, he was going out of his mind. Y/N looked fantastic and it was only making things worse. Her legs looked awesome in the denim shorts she was wearing, she had a white body suit on underneath and a leash jacket on top, matched with a nice pair of white sneakers that had little beads on them.
"You know, Everyone already considers her your girlfriend." Jamie shrugged as the two men looked over towards the group of girls. They were keeping their distance and talking about their own things, but watching just in case the gals needed them.
'Fuck I know that- Even I consider her my girlfriend, I just don't think she considers me her boyfriend." Tyler crossed his arms, pouting like a puppy. All he wanted was to be able to kiss Y/N and call her his, he wanted to be that stupid mushy couple that did couples workouts together and everything.
Jamie sighed. "You need to tell her how you feel man, be honest about it." He turned his back towards the bar and ordered another drink before glancing at his best friend. "Drop the pick up lines and tell her how you feel." He ordered his buddy. It was playful and if he was lucky, Tyler would actually listen to him.
But Tyler being Tyler, obviously didn't do that. "No no, I've got an idea." He grinned. Tossing the rest of his beer back, Tyler shook his head out and pepped himself up. "Watch this." He nudged Jamie's arm before making his way across the bar.
His captain winced and pinched the bridge of his nose. "Oh god do I have to?" He mumbled under his breath.
Tyler made his way over, greeting the girls before smiling at Y/N. "Hey, we're not socks. But I think we would make a great pair." He smirked at her. Immediately the other WAGs laughed and attempted to stifle their grins at how bad that was.
Y/n just look at Tyler in confusion, innocence and awkward tension splayed across her expression. "Are you asking me to play beer pong?" She tilted her head to the side.
Deciding not to dwell in his failure, Tyler just held out his hand and smiled firmly. "Yeah... yeah I am." He sighed in defeat. Y/N took his hand and they headed off to find an empty game. The hockey player glanced back at the WAGs who were smiling sadly.
"Better luck next time Seggs." Jamie called out.
He received a middle finger in the air for that one.
It took a few more months for Tyler to finally build up the courage to make another move. Y/N was different, she wasn't just some girl that he was trying to hook up with. He wanted a real relationship with her, which is why this had to be perfect. When he had finally grown a set of balls, he was back home in Brampton.
His cousin Charlie was getting married and Tyler had flown home for the occasion. He didn't want things to be awkward so he had asked Y/N to come with him as his plus one. He paid for her flight and everything- even though she was high against that idea. Somehow, Tyler had managed to convince her to let him pay, the two of them flew down from Dallas for the weekend and would be heading back on Monday.
The wedding was beautiful, Charlie and his wife Katherine had gotten married in a large church with stained glass windows. Everything about it was perfect, a white wedding complete with flowers and even doves. Charlie had really out done himself. Watching His cousin get married had caused Tyler to feel a pain in his chest.
He wanted that.
Even though he was seen as this big party fuck boy type, Tyler really did want to settle down and get married one day, he wanted kids, a big house with a white picket fence. He wanted the perfect American dream life- and there was only one person he wanted that with.
Y/N had been such a trouper through the whole wedding, she barely knew a handful of people that were attending, only knowing Tyler's immediate family from parties and the times they've visited Dallas, but nonetheless she had put a bright smile on the entire time, she talked with Tyler's aunts and uncles like she had known them for years- she was the perfect date.
As the two of them last at the reception table, Tyler let his gaze drift away from the newly weds as they took their first dance to Y/N. She was watching on fondly a pleasant smile resting upon her lips. He could see that she was imaging just what it would be like when she finally got married and took her first dance. If he was lucky, hopefully he would be the one dancing with her.
Letting his hand drift under the table, he took ahold of her thigh, just above her knee- it wasn't sexual or scandalous by any means, but it was a little bit more than the usual friendly touches he gave out. Leaning over and whispering in her ear. "You know- they don't have to be the only Romeo and Juliet... that could be us too." He chuckled. "Young and in love."
Y/N turned towards him, a furrow in her brows. "You know they both died in the end right?" She asked. Her hand rested against his- almost as if she was checking to see if he was well mentally.
Tyler looked at her with a hurt expression, he really thought that this would be the time that she caught on. But maybe she didn't like him. It had never occurred to Tyler that Y/N was simply not interested, and suddenly he felt like a fool. Sighing heavily he let his hand drop from her thigh and turned his back to her- watching the couple dance.
Through the rest of the night, Tyler was pretty solemn, his family didn't notice as much but Y/N was locked in on his emotions. As soon as she got the chance, she was pulling him away from his mother and taking him back the hand- leading him outside into the courtyard, they walked quickly. Y/N could feel her short sundress brushing against her legs from the speed she was taking.
Tyler almost had to jog to keep up with her. With a crease in his brow, he didn't understand where they were going. "You okay?" He asked once they had finally stopped.
Y/n looked at him and bit her lip. "I think I should be the one asking you that." She crossed her arms. "Ever since Charlie and Kathy took their first dance, you've been pouting like a hurt puppy..." she looked into his eyes deeply.
Taking a step forward, she cupped his cheek. "Whats going on in that head of yours Ty.." She caressed his jaw. In that moment, Tyler thought he might cry- never had he felt so in love with someone.
He had to tell her.
"I can't do this anymore Y/N." He sighed shakily. The girl looked at him with wide eyes, full of concern as she tried to figure out exactly what he meant by that. "I can't keep doing this- I am so in love with you and its like you don't even care." He had a sense of urgency in his words.
Y/N was struck, she didn't even notice that Tyler felt this way but now he was pouring his heart out to her and she felt like an idiot.
Tyler sighed softly. "Ive been hitting on you for months and you either brush it off like a joke or just ignore it- I can't keep doing it... I just- I need to know." He took a step towards her and let his hand fall to her waist.
"Do you wanna go out with me?" He asked bluntly. He had been relying on his flirting skills for too long- it was getting him no where and now it was time to just suck it up and be straight forward.
With flaming cheeks, The girl looked down. "I didn't even know you were hitting on me Ty... I thought you saw me as like a best friend- Which is really dumb.. because you're not supposed to fall in love with your best friend." She looked back up at him with a grin.
The hockey player was almost lost for a second. He stumbled over his words before asking for clarification.
Y/N laughed softly. "I love you too Tyler... Ive just been too nervous to say anything." She sighed. The man in front of her visibly relaxed. He wrapped her up in his arms tightly and pressed a firm kiss to her lips.
"Were both pretty dumb huh?" He asked, pulling away and chuckling softly, wrapping his arms around her shoulders, the two of them headed back into the wedding- ready to party the night away and just celebrate love.
As the two of them danced the night away on the floor with the rest of the bridal party, Tyler's parents watched from afar.
"Weddings huh?"