Your brother Dustin had been trying to set you up with his newly acquired friend for ages. He was well aware of the lack of romance in your life and knew that you and Robin Buckley would be a perfect match. Just like Robin, you were upfront and sarcastic, yet sweet and caring at the same time. You’d tease Dustin relentlessly, but it always came from a place of love. The same way that Dustin would annoy you just to get you frustrated, but really he wanted to spend time with his older sister. He knew that if you just gave it a chance, it would make the both of you so happy. But just like Robin, you were stubborn. So he knew that convincing either of you outright would be met with resistance. His solution to this was roping in Steve Harrington to get you two together. Although this was a hopeless solution. Despite Steve’s claims that he was ‘sneaky like a ninja’, he was anything but.

Nonetheless, Steve had successfully weaseled his way into your life, and you considered him a good friend. Which is why you had agreed to go to his house for a small get together. His idea was that a few drinks and a good party could be the push for you and Robin to make a move on each other. By this time, you’d hung out with her a few times, and though you didn’t tell Dustin this, you definitely liked her. She wasn’t like the other girls you’d previously had a crush on, instead she was a breath of fresh air in comparison. You just didn’t know how to go about it. The last person you confessed your crush to had utterly rejected you, leaving you feeling insecure about opening up to someone new in fear of a repeat in history. It was silly, but you decided that it would be better to push your feelings down.

The night of the party you got dressed into something simple but cute. A yellow floral buttoned-down dress, paired with some black bootie heels and a denim jacket. You decided to go for a dewy makeup look, and you curled your hair into thick waves. As you were finishing up your final touches, the sound of your bedroom door creaking pulled your attention to your brother. “You look great (Y/N)!” Dustin sang with two thumbs-up. You shook your head lightly, “Thanks, but I just look basic”. “No! Come on, you’ll be the talk of the party” he retorted. “Stop!” you laughed back, but secretly appreciated his compliments, you needed the confidence boost.

Once you arrived at Steve’s, you were greeted with a glass of whatever alcohol he was able to steal from his parent’s stash. You tried to mingle with his friends, making a few jokes here and there. The mood of the party lightening up, everyone was having a good time. Everyone but Steve who was getting more and more frustrated by the minute. Every time Steve tried to act like cupid, something would go wrong. When he wanted to get you and Robin to speak to each other, you would find an excuse to walk away, claiming you needed a refill or to go to the bathroom. He decided to try one last time.

“Who’s up for a game of spin the bottle!” Steve shouted over the music. Somehow, he got the two of you to agree. Now you sat in a circle of eight people, with Robin sitting beside you. When it came your turn to spin, your anxiety was high. As you spun the bottle with your sweaty palms, it felt like time had slowed down. What in reality was a few seconds felt like a few hours. The tip of the bottle spinning past Robin a few times. You closed your eyes as you waited, eagerly hoping for it to land on Robin. A gasp from one of the partygoers awakened you. It had landed on Steve.

“Just my luck” Steve scoffed, thinking he had said it internally. When he saw everyone’s face turn to a shocked expression at him, he’d realised that he’d said it out loud. You didn’t even want to kiss Steve. Still, the embarrassment of being rejected even in a stupid game brought up feelings that you’d longed to forget. With a blushed face, you quickly got up and ran outside. Steve felt horrible. He hadn’t meant it like that, he just wanted the bottle to land on Robin as much as you did. “I’m gonna go speak to her” he broke the silence. “No, you stay here. I’ll check on her” Robin responded. 

You were sitting on one of the pool loungers staring off into the distance. God, I just made a fool out of myself, you thought. Your self-pitying was disrupted by the sound of the chair next to you being moved closer. “Hey (Y/N), are you alright? You know what Steve’s like he’s just an idiot. He’s lost all his game, and he probably couldn’t handle kissing a pretty girl like you” Robin softly remarked, trying to make you feel better.

“You’re just saying that. I’m not pretty. I tried to make an effort to look nice today, but I look stupid. I don’t know why I thought I’d be enough for anyone” you sighed feeling tears forming your eyes. Robin gently touched the side of your cheek to make you look at her, “, I know this is probably a long shot because you obviously like Steve. But would you ever consider going on a date with me?” Robin asked. You were shocked, your mind racing back and forth. Was this really happening?

“I don’t like Steve!” you laughed. Robin looked at you, inquisitively. “I like you! I was just upset because I was embarrassed. God, I was trying to pretend like I wasn’t interested because I thought you were too good for me!” you continued. Relieved that the feelings were mutual, you agreed to go on a date with her the next evening.

Unbeknownst to you, Steve was watching the interaction between you and Robin internally jumping for joy, he couldn’t wait to tell Dustin that his plan had worked. Although he might skip out on the part that he made his sister cry. Maybe he wasn’t such a lousy wingman after all.