Dylan O'Brien Imagines

Say Something

Dylan is your best friend, nothing more. You help each other with everything, so it only makes sense to come to him when you have boy problems. After all, he is the only guy you feel you really can trust. You are both laying on your bed watching tv when you decide to bring up a topic that's been on your mind lately.

"Hey Dyl."

Dylan stops throwing your pillow up in the air to sit up and look at you. "Yeah?"

"You know how that guy came up to us and was talking to me earlier? Was he flirting with me or just being friendly?"

He chuckles and rolls his eyes before saying, "He was definitely flirting with you. You couldn't tell?"

Of course you couldn't tell, guys never openly told you how they felt. "Well it's not like I have a lot of experience with flirting. I don't have that much experience with guys at all, really."

Dylan mocks you by responding with, "Then what am I?" as he nudges you with his elbow.

"Come on, you know what I mean. Like kissing, flirting, dating, that stuff..."

He squints his eyes and tilts his head. "Wait, you've never kissed a guy? Not even a peck? How did I not know this? You're my best friend!"

You try your best at avoiding eye contact when you say, "Thats not something you brag about. I didn't really think it mattered. But now that I know that guys are like, interested in me, I guess it does. I don't even know how to kiss a guy, how pathetic is that?" Dylan always makes sure you feel comfortable telling him about your personal life, but it's embarrassing when you don't really have a personal life to discuss in the first place.

"It's not that hard. Your first kiss is always the worst one. Once you get past that, every other one will seem like a piece of cake. Maybe... Maybe I can teach you. That way your first real kiss will be your second actual kiss. Did that make sense? It sounded better in my head."

"Yeah, that makes sense. We should kiss. For teaching purposes."

"Of course, for teaching purposes..." Dylan tilts your chin up slightly before leaning toward you. He gets close enough that you can feel the heat from his breath on your mouth, and then his lips press ever so gently against yours. You close your eyes as your lips lock for a couple of seconds and Dylan pulls away. You open them again to see him staring back at you intensely. Without thinking, you go in for a second kiss. Dylan doesn't pull away from this one, instead he pulls you toward him as the kiss continues.

His hands slide up your arms and you get goosebumps. You aren't sure if you're even doing the whole kissing thing right but he doesn't stop you so that must be a good sign. You place your hands against his chest as your kiss intensifies. Dylan breaks away again, and this time you realize you two may have been a bit too into the kiss that was solely for "teaching purposes".
You immediately stand up and occupy yourself by finding some random thing to clean in your room, too embarrassed to face your best friend when you let out, "Uh, thanks for... Whatever that was. We can forget about it if you thought it was weird."
He stands next to you and starts fidgeting with his hands by running them through his hair before he responds. "No, it wasn't weird. Well maybe, but not for the reasons you think. I'm just realizing that I kind of don't want anyone else to kiss you like that."

"Kiss me like what?" You aren't sure if he means this in a protective brother type of way or a jealous boyfriend way.

"Romantically I guess. I don't know what I'm saying, I'm really tired... Y/N, I know we're best friends and all but it just felt different when we kissed. I mean, I've always kind of had a thing for you, I just never said anything."

So many questions rush through your mind. How could he have had feelings for you this whole time and not tried to pursue them? Did anyone else know? "Why didn't you ever tell me anything? You should have said something."

He bites down on his nail and looks at the floor. "I had the biggest crush on you when we first met but you didn't seem interested so I just let it go."

You repeat under your breath, "I wish you would have said something."

Dylan hears you and says, "I'm saying it now. I regret not telling you, but I can't go back in time. If I could I would have kissed you the first day we met."

Of course the thought of Dylan being more than a friend has crossed your mind from time to time, you just never imagined it actually happening. You never even realized how badly you wanted to call him yours until now. You take a bold step and wrap your arms around him before planting your lips on his for the third time that night. He's stiff from surprise at first but soon kisses you back with the same amount of passion as before. Who said best friends can't become boyfriends?