Slenderman
You and Slender were once again in the Proxy Mansion he was making you dinner and you seemed so unsettled, "Slender are you sure you don't want my help?" You asked.
"(Y/N), please let me do this." He said as he prepared the food.
You heavily sighed and sat there waiting for Slender to finish.
While you waited someone came in the dinning room; you glanced and a young girl with long, dark brown hair, around the age of 6, in a pink night-gown entered.
She stared at you with unblinking green eyes and a wide smile. She had deep cuts covering her face, and her hands that hung at her side while holding a teddy bear.
You both sat and stood staring at each other for a good moment, until she let out a horrifying, high pitched scream, "YOU'RE SLENDY'S GIRLFRIEND!"
You covered your ears and Slender came running in, "Sally! don't do that sweetie." He covered her mouth as she screamed long and hard.
"But Slendy that's your girlfriend." She tried whispering but you still heard her.
Slender nodded and told her to leave and she passed you and smiled then left skipping, "She's cute." You said laughing slightly.
"She is but anyways food is ready." He went to the kitchen and brought the plates out containing (Favorite Meal), "I hope you like it."
You smiled and said, "Impressive for a first date."
"I hope." He said as he turned into his human form.
Jeff The Killer
You and Jeff ate out at a place called Linsey's Pizza. You guys were sitting down at a table waiting for the three full pizzas you guys ordered.
"Jeff thanks for taking me out." You said smiling as you took a drink from your glass.
"Got to take my babe out." He said as he flashed that sinister smile you loved so much at you.
You looked around to see if your pizza was coming. You noticed people were staring at Jeff trying to get a good close eye on what he looked like. You slightly heard people whispering saying His mouth is cut or what is she doing with him?
You looked at Jeff and shly said, "Jeff, kiss me."
He looked at you with a crooked smile and kissed you roughly and you put a little tongue in the kiss. He pulled away and said, "Woah babe, save that for later." He playfully said as he winked.
You giggled and looked at him. The pizza came and you guys ate (Three Favorite Pizza's).
After you guys ate you headed home. Holding Jeff's hand he stopped and stayed, "Jeff...What's wrong?" You asked.
"Thank you for doing that," he said slightly releasing your hand, "Anybody else would have left."
You held his hand and smiled softly, "Jeff I'm not just anybody else."
He pulled you close to him, "Yeah you're better." He gave you that crooked sexy smile and kissed you.
Eyeless Jack
You and Eyeless Jack were eating at your house. You and him were wating for the (Favorite Food) to finish cooking.
He looked at you and smiled, "This date is going pretty well."
You nodded, "Very much."
You guys talked more about the Proxy when the oven started smoking. You quickly got up and Jack opened all the doors and windows while you pulled the fire extinguisher out.
"No..No.." You cried.
He went to you, "Babe is okay." He said comforting you.
"No I wanted this to be special it's our first date." You begin to tear up.
He hugged you and said, "Don't worry babe I'll order something." He grabbed your phone and called (Favorite Place To Deliver).
Minutes later the (Favorite Delivery Place) man/woman came. You opened the door and payed for the food and gave him/her a tip and closed the door.
You sadly walked to the kitchen where Jack was sitting down at the table waiting for you to come, "(Y/N), its okay if it makes you feel better I would have burned this whole place down in seconds don't be hard on yourself babe." He said lifting his mask and eating the food.
You smiled ever so slightly and said, "I guess your right." He finished chewing and kissed you softly.
Hoodie
You and Hoodie went to a park. You guys decided to have a picnic and glaze at the stars. You assumed Hoodie was planning on staying there for a while because he brought a couple extra blankets.
"This is going to be fun." You happily said.
Hoodie laid out the first blanket and laid two more leaving one off to the side. You sat down and he pulled the cooler towards him pulling out (Favorite Sandwich & Chips & Drink).
You kindly took the food and drink and said, "Thank you honey-bun."
He laughed and said, "Honey-bun?"
"Yes, cause you're so cutie!' You said getting up and kissing him.
After you and Hoodie ate you laid down and Hoodie got the extra blanket he put off to the side and covered you and him with it.
"(Y/N), was this a good date?" He asked.
"Oh, yes very much yes." You hugged him tight, "The best ever."
"I'm glad..I wanted tonight to be special."
"Awww Hoodie no matter what it would've have been special." You said as you kissed him carelessly. He hovered over you and continued kissing you.
After a while you separated from him to catch your breath and smiled at him. He laid down and you laid your head over his chest feeling his chest rise and his heart beat fast due to your make out session a few seconds ago.
The stars were shining tonight. You snuggled up with him and heard him go on about the stars and the hidden pictures within them.
Ticci Toby
You and Toby went for a walk on the beach. You didn't want to eat you just wanted to spend time with Toby.
He held your hand and slightly twitched, "Are you sure you want to just be here?" He asked.
"Yes, I just want to spend time with you and that will be a perfect first date." You said releasing from his hand.
He nodded and said, "Okay.."
You guys walked parallel, reaching for his hand you grabbed his pinky and held onto it. He twitched and you slightly and gently started swinging your arm and his arm as you held onto his pinky.
"Are you at least having fun?" He said holding your hand fully.
You stopped and looked at him, "Yes Toby, Are you not enjoying yourself?"
"As long as I'm with you I'm happy with no care in the world, (Y/N)." He said as he pulled you towards him and pulled his sharp tooth mask off slightly.
"See? That's how I feel Toby." You said wrapping your arms around his neck.
He smiled and put his arms around your waist pulling you close to him as possible and looking at you as if he was admiring you.
You slightly tiptoed making yourself a little taller and kissed him. He picked you up and kept kissing you; wrapping your legs around him you carelessly and passionately kissed him.
A few seconds after your full make-out session he pulled apart from your lips and breathlessly smiled, "Good first date?" He asked
Having your forehead resting on his a few centimeters away from one others face still wrapped with him as he carried you and you softly whispered, "Yes."
He kissed you one last time and slowly put you down rubbing your body gently on his; you and Toby held hands once again and contuined walking.