Creepypasta Boyfriend Scenarios

He Asks You Out..(kind of)

Slenderman
You knew it was coming, honestly. Slenderman may be some all powerful mythical being, but he's still got the body language and brain of a boy. And if there's anything you understand at least a little, it would be boys.

Slender was surprisingly too nervous to ask you in person. Rather, leaving six notes throughout the trees along the main trail reading "Will You Be My Beloved? -Slender". Of course, once you found him and the cute scene he set up, you agreed to be his girlfriend. Your main concern, however, was what he would have done if someone else had found the notes before you did.

Jeff the Killer
Jeff didn't ask you out, you asked him out. He kept flirting with you, more than he usually would have, and at one point he even held your hand, and refused to let go for quite awhile. While it was a fun game to play for a little bit, but eventually you just got tired of it.

"Jeff, we either start dating or you cut all this flirty shit out," You had a slight demanding tone, and you were hoping that would help you get your point across to him.

He just looked at you like you were dumb for a minute, "Okay. We're dating, then. Can I have a hug now?" That was the end of the conversation, completely.

BEN Drowned
BEN being cliché, he used video games to ask you. He gave you a game, it was for (choice console i.e. PlayStation, Xbox) and told you to play it. It wasn't a video game you had ever heard of, and some of the questions were weird, like your favourite colour, birthday, full name. You went with it, however. Because BEN told you to and if he liked a game and recommended it to you, he knew you'd like it.

Finally, after what felt like a million and seven questions, came the character destining phase. You tried to change certain aspects, like the hair style and clothing options, but it wouldn't let you. The character actually looks strangely like you already. You gave up trying and clicked the next button, when a dialogue option came up.

(Y/N), will you be my girlfriend?

Your only options were yes, definitely and absolutely. You chose absolutely. The second you pressed enter, BEN popped out of the screen and gave you a hug. You screamed a little due to the surprise, you hugged him back nevertheless.

Eyeless Jack
Jack, of course, used cheesy pickup lines and jokes to ask you out. The day with him started normal, telling random jokes as you thought of them. His, however always sounded like cheesy pickup-lines.

This proceeded until he had to leave, which at this point, he looked at you and said If I had a star for every time you made my day brighter, I'd have galaxies in my hands,"

You were confused and kind of dumbfounded. That one was definitely a pickup line. After asking Jack what that meant, he asked if you'd be his girlfriend. And there's no way you'd ever tell him no.

Dark Link
Dark had always been very blunt with you, and when he came into your room and demanded you be his girlfriend (his exact words: "(y/n), we're dating."), you decided to mess around for a minute just to make him nervous.

"No," You said blandly, not looking away from your book.

"W-What?" His face fell, and he looked as if you just crushed his heart, "Why not? I-I thought-"

"I'm kidding, Dark!" You smiled, "I'd be honoured to be your girlfriend."

"You ass!" He barked, "I was scared you had actually said no!"

"Maybe next time you should ask instead of demand," You told him, "Now come here, I would like a hug, please?"

Lost Silver
Silver was already a really shy guy, and asking you out, possibly one of the most difficult things he had ever done. All of the possible things that could go wrong played in his head, he nearly talked himself out of it.

"(Y/N)?" You heard his soft, shaky voice call from the other end of your bed.

"Yes, Silv?" You replied, looking up at him.

His cheeks were a bright red, "Will you..will you puh-please be my, uh, muh-my girlfriend?" Silver quickly turned away, not wanting to see your face.

"Oh, Silver, of course I will." You crawled out of the covers and over to sit next to him, "You're pretty cute when you're nervous, not going to lie."

Ticci Toby
Toby had genuinely never given you a single hint to show that he liked you back. Aside from when he reacted strangely to your friend being at the pond that once, you honestly would have guessed he didn't really want anything aside from being acquaintances.

"Hey (Y/N)?" Toby glanced over at you, taking off his goggles. That's how you knew this would be serious, his goggles hardly ever came off the top of his head.

"Yeah, Toby? Is everything okay?" You obviously sounded a little worried.

"Can you be my girlfriend?" The question didn't process in your mind for a second, but when it did you said yes.