Slenderman

Slendy had been out of it for a while now, and you were starting to wonder what was wrong. He was acting nervous, but you finally got to find out why today. "Hey, (Y/N)," he said quietly.

"Yes Slendy? What is it?" you asked curiously.

"Well... I was just wondering... doyouwanttogooutwithme?" He rushed the last part, and it took you a moment to process what he had just said, before you tackled him in a hug.

"Yes!" you said happily. You heard Slender sigh in relief.

Jeff the Killer

You and Jeff had been hanging out all day, and you couldn't help but notice how jittery he was being. "Jeff, is something wrong?" you asked.

Jeff stopped dramatically staring out the window and turned to face you. "I'm just..." he blushed.

"What? What is it?" you pressed.

"(Y/N), I'm just afraid you'll say no." he basically whispered.

"Say no to what?" Now you were really curious.

"To..." he took a deep breath. "To going out with me."

You grinned and smothered him in a hug while basically squealing "Yesyesyesyesyes!!!!!"

Eyeless Jack

Jack had been unusually silent today, and it was starting to freak you out just a bit. He had only said three words all day. But now he turned to you. "(Y/N), can I take you somewhere?" he murmured.

"Yes," you said a bit hesitantly. He grabbed your hand and basically dragged you outside. "Where are we going?"

"It's a surprise," was all he said before he fell silent again.

You two had walked for about ten minutes before you arrived at the park. EJ pulled you to the tree you guys sat in whenever you came, and he sat down right next to it. "I wanted to ask you something, but I wanted to make it special."

"Okay. What?"

EJ took a deep breath. He seemed incredibly nervous. "(Y/N), would you like to..."

"To what?" you asked with a smile on your face. You knew where this was going.

"B-be my girlfriend?" he stuttered out.

Your smile turned into a grin. "Of course!"

He sighed in relief. "Good, because I already have something set up." He led you to a pavilion where lunch was set out. And so your first date began.

Masky

You heard a knock on your front door, and curiously went to open it. You turned the doorknob, swung the door open, and there stood Masky, with his hands behind his back. "Hi, Masky!" you chirped happily as you gestured for him to come inside. He walked in and glanced around, given he had never been in your home before. "What brings you here?"

"I have a question for you, (Y/N)," came the reply.

"Okay. Shoot."

Masky brought his hands in front of him to reveal a bouquet of (your favorite flowers) as he got down on one knee like he was proposing. "(Y/N), will you be my girlfriend?" he asked.

You grinned and took the flowers. "Yes Masky! Of course!"

He beamed under his mask and got up to hug you.

Hoodie

You and Hoodie had been hanging out all day, but he seemed to be avoiding something. "Hoodie," you said for the tenth time, "Why exactly can't I go home?"

Hoodie remained silent and didn't look at you. You sighed and looked at the time. "It's five thirty," you said. "How much longer?"

He finally turned to look at you. "H-half an hour, (Y-y/N)."

You sighed and continued with what you were doing.

(TIME SKIP)

Six o'clock rolled around and Hoodie dragged you home excitedly. You unlocked the door and headed for your room. When you entered, you audibly gasped. Your room had been transformed into a dinner-for-two mini restaurant, complete with a basic table with a tablecloth and a rose in a vase in the center, romantic lighting, and music.

You turned to face Hoodie, who was looking at you fondly, with his mask removed. "Hoodie," you whispered. "Hoodie how did you...?"

"I c-called in a few f-favors," he said simply. Then "(Y/N), w-will you be m-my g-girlfriend?"

You beamed which caused Hoodie to mimic you. "YES!" you screamed. He laughed and led you to the table where your date began.

Ticci Toby

Toby had taken you out to eat, and he was fidgeting with something in his pocket, occasionally cracking his neck uncontrollably. "(Y-y/N), I h-have s-s-something t-to ask y-you," he said, stuttering more than he usually does.

"What is it, Toby?" you asked, a bit concerned.

Toby pulled his hands out of his pockets, along with a small box. He opened it to reveal a beautiful golden ring with a sapphire in the middle. You gasped at its breathtaking beauty. "I-it's a p-promise ring," Toby explained. "Y-you can have it i-if you p-promise to be my g-girlfriend," he said with a hopeful expression.

"Toby, yes!" you said like it was the most obvious answer in the world.

He grinned under his mouthguard and slipped the ring onto your right hand's ring finger.

BEN Drowned

You were playing video games with BEN,and you were winning. "Oh come on!" BEN exclaimed. "You know what? If you win the next round, you have to be my girlfriend, deal?"

You grinned, knowing he'd probably lose on purpose. "Deal."

You two started the next round, and, needless to say, BEN lost.

~~

Hi guys! Yay! Next chapter! I should probably spend some time with my other book, but I'm just having so much fun with this one! It's a problem. Possibly. Anyway, how'd you like this chapter? I think it was pretty good. Well, I have to go now, so I'll see you in the next chapter! BYE!

~MishaIsOurOverlord1