some shy human stefan was requested and although requests are closed, this was coming up next anyway so here you go !! i love writing these kind of stefan imagines more than anything honestly, they're my favorites and i hope you guys like them too ((:

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Imagine you and human!Stefan meeting Katherine Pierce for the first time through Damon and pretty much everything goes awfully wrong

"Y/N, Stefan, this is Katherine."

You gave a disapproving look to Damon, who was introducing the new girl with a smile. You had no clue what was going on with him and this Katherine, but you knew for sure that you didn't want her around your Stefan with her fancy, way too revealing dresses, or her curly hair or her seductive smile. You weren't too insecure, and you didn't have any reason to be jealous either, until now. Katherine looked like a goddess, and when you saw Stefan blushing and kicking the ground like when he did around you, you couldn't help but feel anger and jealousy break into you.

You grimaced, but put on a fake smile when Katherine shook your hand in a friendly way. You were kind of hating her though, because even though she seemed nice and all, she was too pretty and who knows what kind of a whore she could be. Maybe she'd attempt to steal your boyfriend. Your clueless, adorable, innocent boyfriend who was staring at the new gorgeous face in front of you two like a kid in a candy shop.

"Damon, can I speak to you for a second?", you asked through gritted teeth, and the young man nodded and walked to the side with you, ready to hear you out. But instead of starting to speak, you smacked the back of his head and glanced at Stefan and Katherine, who was already all over the poor boy. Flirting, giggling and putting on a nice little act. You were a good girl, kind and everything, but right now you wanted to bury the bitch alive.

"Ow, Y/N, what the hell?", Damon asked and rubbed the spot you hit with your hand, while giving you a confused look. You shuffled on the ground uncomfortably and glared at him, and then at Katherine.

"Why did you have to bring her with you? I-I don't... Look at her. And Stefan. And uh... I- Damon, you're an idiot", you groaned in frustration. You had never before felt jealousy, not like this at least, and it was eating you from inside, poisoning your good golden heart. The toxic feeling took you over as you sent daggers with your eyes to Katherine, who didn't seem to notice, just smiled and continued to talk about something with Stefan.

Stefan was your boyfriend, and he was in love with you - why did this girl have to come and try to tear you apart?

"What- Ohh. Oh! Oh, you're jealous, aw, of course. C'mon, you're over-exaggerating though, especially with Stefan being so clueless and dumb and innocent. Look at him. He's never going to understand when a girl is flirting with him", Damon said, "Besides, I'm hoping to get something going on with Miss Pierce, so I promise I will keep her paws off of your precious baby boy." You scoffed and looked at Stefan. He was kind of dumb, you thought, in a good way. Enough to not pick up hints or attempts at flirting, but not dumb. A faint smile covered your lips as you looked at him, he was so short and small and skinny and cute as he stood there, fiddling with his fingers.

"I-I am not jealous, Damon!", you began, but Damon cut you off by laughing.

"Yes, you are, but I completely get it, Y/N. Katherine is pretty decent looking, and you are hopelessly in love with my brother so it's only logical to feel that way. But I swear, Stefan would never cheat on you, nor understand the magic of flirting. Keep calm, because everything is just fine", he chuckled, and patted your shoulder. You bit your lip thoughtfully, but nodded then, and walked to the two of them with Damon.

You had a dinner to attend, anyway.

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"This is Y/N's favorite restaurant", Stefan said proudly, when you, him, Katherine and Damon entered a place that was indeed your favorite. You smiled and took his hand, which managed to bring that pink coat of blush back to Stefan's cheeks as always, and it made you smile. Everything was just fine. Just like Damon promised.

You were seated at a table in a corner, where you sat next to Stefan and Damon sat next to Katherine. You found yourself looking at Katherine with a judging look, and a hateful one too, but when Damon gave you a firm glare, you looked down at your hands and blushed. You weren't a shy girl, but it seemed like today your personality wasn't the way it usually was.

"So, Stefan, are you and her, like, together?", Katherine questioned after a waiter had taken your orders and left your small group alone. It was like you weren't even there, she wouldn't bother to even glance at you, and she was talking to only Stefan, even when she talked about you. You kicked Damon's leg under the table, and he looked up from the table, and noticed Katherine smiling an innocent, yet flirtatious smile at his brother, and your boyfriend.

"Yes, they are, Kathy. In fact, I believe there's been talk of marriage, correct?", Damon cleared his throat and gave a look to Stefan and you. The shy boy next to you blushed, again, and scratched the back of his neck awkwardly. Marriage? Was Damon just making up something, or had Stefan really talked to him about asking you to marry him? Because although you would say yes, and loved the idea of getting married with Stefan, you hadn't thought about it, and definitely not spoken about it to anyone.

You gave Stefan a surprised look, and he started to stammer and play with the hem of his shirt uncomfortably. He didn't like to be under pressure like this, with everyone's eyes on him, and he could just ramble and hope for something reasonable to come out of his mouth.

"I-well, uh, I mean- I don't think- Well, um, we are... I, uh, I do l-love Y/N very much... And I guess- though, uh, I don't want to, um, pressure her into a-anything, you know? I mean...", he stuttered, uncertain of what to say. Damon had tried to make the situation better, but he had only put Stefan into an uneasy place, and you groaned. The sound was taken as something negative, though, and Stefan gave you a horrified look, as if you were done with his shy attitude and didn't want to marry him.

"I... Uh, Damon... Thank you. I'm gonna- I need air", Stefan whispered, his voice weak and cracking and you were quite sure he was going to cry soon. So you gave Damon an angry look, before getting up and running after Stefan who had stormed out of the restaurant with his small feet, his tiny body sneaking from between people and finding his way to the street where he absolutely broke down.

"What did I do?!", you could hear from behind you, but you had no time to stay inside. Your boyfriend was a shy, adorable mess and falling apart because he was also insecure and easily thought you didn't love him the way you used to.

You went outside, and there he was, crying against the wall, the whole poor boy trembling and shaking with fear and sadness. You let out a sad sigh, and walked to Stefan. You pulled him into a hug, wrapped your arms around him and held him tightly. He was too weak to pull away, so he just cried into your arm, although he was scared that you didn't want to be with him.

Things took an abrupt turn, to a much worse direction. This was a million times more horrible than you feeling jealous over something not worth the feeling.

"Stefan, please stop crying. I love you, I really do. You're so cute, and handsome and great, and I do want to marry you one day. I promise that whenever you find the courage to propose to me, I'll say yes. Because I love you. I was feeling jealous a moment ago because of Katherine, but you love me too, right?", you talked to him, trying to calm him down. He suddenly lifted his head and looked into your pretty eyes with his own, red ones and made you frown at the sad, heartbreaking sight.

"Jealous? You?", Stefan asked, and you nodded while wiping his eyes. He was quiet for a while, but then broke into an adorable laughter, that made you smile faintly. "Y/N, I'm in love with you and I always will be. There is no reason for you to feel jealous. Katherine might be nice and all, but she's nothing compared to you", he continued, and pressed his forehead into yours. You smiled, and kissed his lips gently, causing him to whimper and sigh adoringly.

"I love you, Stefan."

"And I love you, Y/N."

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"So... Everything's okay here? Right?", Damon made sure when you and Stefan returned to the table where he was with Katherine. He was truly sorry, and worried too, because he knew how fragile his brother was and how much he loved you. And he wanted nothing but happiness for you two, and was going to keep Katherine away from Stefan, in a safe distance at all costs. He did not want to see his precious baby brother get hurt. Sure he was picking up fights almost every day, but he knew that losing you would be the worst thing ever. It would hurt more than anything, or everything put together, really.

"Perfect", you said, and looked at Stefan with a smile, who mirrored the expression happily. You and him had barely sat down, when Katherine leaned over the table and closer to Stefan again, making the blood in your veins threaten to boil up, but Damon noticed and aimed to do something about it, but surprising you both - Stefan spoke up.

"Please, Katherine. You're cool and all, b-but... But I love Y/N and I think you should stop trying so hard", Stefan said, though it was awkward and careful. He didn't want to hurt Katherine's feelings, but he definitely didn't want you to feel bad either.

"Yeah, Katherine", you said and threw your arm over Stefan's shoulder, "he's mine", and gave your boyfriend a big smooch. He blushed and Damon laughed, while Katherine awkwardly leaned back into her seat and twirled one of her curls around her finger.

You had no reason to be jealous anymore, and Stefan didn't feel bad either. In the end, everything went perfectly for the two of you.