Vampire Diaries Imagines And Preferences

Imagine #17: Damon & Stefan

Imagine liking Stefan but you're too shy to ask him out so Damon helps you out

You have had a deep crush on Stefan for the longest time, and yet no one was aware of it. You happened to be good friend with him, but there has always been something going on between you two, and you both knew it, but you were afraid of facing the truth and admitting it. You wanted to ask him out, more than anything, but you never mustered enough courage to look him in the eye and confess your love for him. You had attempted to tell him how you truly felt towards him, and each time, you failed. Whenever you spoke to him, you always panicked and ended up wimping out. You didn't know how to approach him or act around him without embarrassing yourself, and you figured out that keeping your feelings anonymous would be safer. You assumed that Stefan only liked you as a friend, and for that reason, you doubted that he would accept to go out with you. What if he rejected you or laughed at your face? All those negative thoughts haunted your mind. You weren't willing to take the risk of ruining your friendship, and you couldn't even bear the thought of losing him either. This whole situation bothered you, however, you couldn't find a way to fix it.

Thus, you sat back and fantasized about how you and Stefan would form a great couple. You kept your feelings buried inside of you, wishing that maybe, someday, he might be yours. Your feelings for him only grew bigger every day and it killed you not being able to call him your boyfriend, but you still clung onto the hope that your friendship would turn something stronger. However, you knew if you didn't make a move, nothing would happen between you two. You gave him several hints to show that you were interested in him, yet he completely missed them. Stefan has always been a reserved guy, especially when it came to girls, which meant that he rarely flirted, and never considered dating someone. 

After a while, you eventually got tired of waiting for something to happen and finally chose to change things. You thought of a more subtle way to ask Stefan out than speaking to him directly, and came up with a solution. You decided to get help and advice from Damon since he had quite a lot of experience in this field. You were hoping that he could maybe put in a good word for you and convince his brother to date you. Someone needed to shake some senses into Stefan and make him realize that you liked him. It might sound stupid and desperate, but like Damon once said, you can't just sit there and wait for life to come to you; you have to go get it. You weren't sure if you could trust him with your secret though, but it was worth the risk. At least you wouldn't have to face Stefan, and you could avoid making a fool out of yourself. After all, maybe your idea would work, who knows? Sometimes, the best things happen when you least expect it. 

You gave Damon a call and asked him to meet you at the grill without telling him why yet. You wouldn't spill details about your plan until you made sure you could rely on him.

"So why did you call?" Damon inquired.

"Swear you won't laugh or tease me about it."

"I can't promise you that." He smirked.

"Damon, this is serious."

"Fine. What is this all about?"

"Okay, so there's this guy I like and I want to ask him on a date, but I'm scared so I thought that you could maybe help me out." You explained.

"Aw, Y/N has a crush on someone. Isn't that cute?" He chuckled.

You rolled your eyes and slapped his arm.

"So who's that lucky guy? Me? If yes, then I wouldn't mind going out with you at all, just-"

"It's Stefan." You interrupted him.

"Stefan? You mean my brother?"

You nodded your head and dropped your head down to hide your blush. His eyes widened in surprise, and his jaw dropped to the floor. He wasn't expecting this answer at all.