"Come on, Ian. You can do this."
Even though he said he could, Ian was beginning to seriously doubt he really could. He'd been stood outside your door for an hour now, trying to work up the courage to knock and finally do what he'd been meaning to do for ages.
You'd moved to the city a year ago and somehow, you'd ended up friends with the nervous, try hard that was Ian Lightfoot. There wasn't much of a story there, you'd been nervous and sat next to the least intimidating looking kid in your homeroom. You weren't expecting to actually enjoy his company, but that was a plus.
Ever since you'd first sat next to him in homeroom, Ian had been totally enchanted. Not like enchanted from magic, though at first, he'd worried maybe it was the result of some ancient spell he wasn't aware of. He'd gone to his brother, Barley, for advice and that's when it really dawned on him.
"You've got a crush!" Barley had yelled at the top of his lungs. Ian desperately tried to calm his loud brother down before someone heard him.
"No- No I don't." He tugged on the collar of his shirt. Was it suddenly ten times hotter in here, or was this his teenage hormones kicking in?
"Yes, you do! What's their name? When do I get to meet them?" His brother placed his hands on his shoulders, shaking him slightly. Ian shoved him away and laughed nervously, not liking where this conversation had suddenly turned.
"Look, I came to you for advice, are you going to help me or not?"
Barley immediately settled down and set to work helping guide his little brother on all the do's and don'ts of dating etiquette. And there was a lot of it. A lot more than Ian had thought there was going to be.
All that preparation had led him to this moment though. Standing outside your door, getting ready to ask you on a date. He had it all planned out. Nothing could go wrong if he just stuck to the plan that he and Barley had so carefully crafted.
He took a deep breath, knocking on the door uncertainly. If he wasn't holding flowers, his hands would be a lot sweatier, he was one hundred percent sure of that.
"Hey, Ian." You weren't surprised to see him. Ian seemed to always show up at the oddest times, but always at the seemingly right times at the same time. Tonight, he'd shown up just as you were finishing your homework for the night.
"Uh, h-hi, (Y/n) ... Flowers?" He held the flowers in his hand out, practically shoving them into your hands. You took them, raising your eyebrows. He laughed nervously.
"Uh, Barley let me borrow Guinevere 2 for the night and I was wondering if you wanted... to come with me?" He could hear the squeakiness in his own voice, and he was internally cringing, hoping that you hadn't noticed it as well.
"Let me just put these away and I'll be right back!" You held up your finger, shutting the door and hurrying to find a place for the random flowers Ian had gave you. As you put them in a vase, your mind wandered to the odd behaviour Ian had been displaying so far tonight.
You and Ian loved taking car rides around the city usually, there was nothing odd about that except for the fact that this time it was going to be in his brother's van. Normally you took your parents car or his mom's car, depending on how late it was and which of your parent's were busy.
His voice sounded different too, though you couldn't exactly put your finger on why. You grabbed your sweater, opening the door once more and shutting it behind you.
"Onwards, best friend!" You wrapped your arm around his shoulder, not noticing the way he slightly tensed up as the two of you walked to the van.
As you got closer, you let go of Ian so you could climb into the passenger seat. He pulled out of the driveway and the two of you rode in silence for a while, driving down random backstreets. A few times you tried to drag a conversation out of him to no avail and a few other times you caught him staring at you out of the corner of his eye, not wanting to take his eyes fully off the road.
"This wasn't how it was supposed to go." Ian finally sighed, sounding really resigned. You turned back to him, surprised to hear his normal voice and not the weird squeaky one he'd used earlier.
"How what wasn't supposed to go?" You asked, watching him as he focused intensely on the road.
"I was supposed to ask you to go somewhere. This was supposed to be a date, but I chickened out. I really like you, (Y/n), but whenever it comes to telling you that; I can't." He admitted, sounding utterly dejected.
You blinked, watching him for a moment before bursting out into laughter. Ian looked away from the road for a second in disbelief.
"What's so funny?"
You shook your head, clutching your stomach as giggles uncontrollably poured out. For a while, the only sound in the van was you laughing. After about 10 minutes of this, you managed to calm yourself down.
"Because that was such an Ian thing to do. You just told me without even realizing you were really doing it, once you stopped thinking about how nervous you were to do it." You explained and Ian flushed, realizing you were right.
He pulled back onto the main street, heading back in the direction of your house. You smiled as you looked out the window.
"Plus, this was a great first date." You told him. Ian made a snorting noise, as if he totally couldn't believe you'd just said that.
"I'm serious. It was just so us. I actually really enjoyed it but maybe next time you should let me know ahead of time we're going on a date, so I don't sit here in silence the whole time thinking something's wrong." You teased.
He stumbled over his words awkwardly as he pulled up in your driveway. "There's going to be a next time?" He asked, hopefully.
You leaned over the center console to kiss his cheek, pulling back and unbuckling your seatbelt. "Does that answer your question?" You climbed out of the van, hurrying to get back into your house.
Ian watched you enter the house, shutting the door behind you. He hadn't followed the plan at all and somehow it had still all worked out. He pulled out of the driveway for the second time that night, this time with butterflies in his stomach and the knowledge that he wasn't the only one between the two of you who felt the way he did.
"How'd it go?" Barley asked, excited as Ian tossed Guinevere 2's keys across the room to him. Ian shrugged, grinning like an idiot and turned to climb the steps to his room.
"I think it went well." Barley sang after him. Ian laughed, shutting the door behind him and flopping down on the bed and sighing.
It had gone better than well.
