~Eyeless Jack~
Jack wanted his first date with you perfect since another guy was after you as well. He was scared that if you didn't like this date, you would go to him. He made reservations at a fancy restaurant and bought you flowers. You had your hair straightened and had a tardis blue colored dress that showed your lovely curves and went to your knees with a pair of black flats. When you went downstairs, you saw a boy standing there in a dark blue polo and black dress pants. "Umm, hi?" You said quietly. 'Who is this guy?' You thought to yourself. Looking closer, you saw brilliant blue eyes and brown hair and had a pretty nice tan. "(Y-Y/N)! You look..." The boy trailed off with his mouth open and you saw love in his eyes. You smiled and went down to him. He held out his hand and handed you the flowers. "Thank you Jack." You said while taking them. You quickly left to go put them in a vase and went back to Jack. How you knew it was Jack you ask? Easy, he sounded and smelled like him. "Ready to go?" He asked. You nodded your head and the two of you went to the restaurant and had a wonderful time together. You didn't mind the way Jack looked on your date, but when you got back to your house you had to ask him. "Hey Jack, is this what you looked me before everything?" Jack smiled and nodded. "Yeah, is it ok?" He asked you worriedly. "Yeah it's hot, but I would rather see what you look like now." He shook his head no. "You wouldn't like it." He said frowning. You frowned back at him. "Jack, I love you not by your looks, but by your personality. Yes I admit that I'm curious about what you look like, but if you don't want to show me you don't have to right now." You finished smiling. Jack smiled back and put his mask back on. "You'll find out later, I promise."
~Masky~
Masky thought it would be a good idea to do something besides eat cheesecake so he took you to a movie. Masky wore a nice shirt with a pair of jeans without his mask on. You smiled when you saw his face and wrapped your arms around his neck. "Why do you wear your mask all the time?" You asked him. "I don't want you to think poorly of me..." He trailed off. You kissed his cheek and giggled as he started to turn a faint pink. "Silly, I love you, no matter how you look. Besides I don't know why your worrying, your hot." He smiled and turned a few shades of red before grabbing your hand and bringing the two of you to the theater. You didn't know what movie you wanted to see so Masky decided to surprise you with a horror movie. You had popcorn and your drinks and quieted down as the movie began. Masky fake yawned and stretched and put his arm around you. You looked at him as he looked at you and you playfully slapped his arm. "What?" He whispered. You rolled your eyes and smiled at his idiocy. "Masky, we're dating. You don't have to pull some cheap move to get me closer to you." You whispered back. As soon as you said that a loud 'BANG' made you jump into his arms and he hugged you close to him. You took a glance at him to see him smiling like an idiot. You returned your attention back to the movie, smiling widely.
~Hoodie~
Hoodie thought that it would be nice to take a stroll in the woods. He had his hoodie on and a pair of dark blue jeans. The only thing different was that he wasn't wearing his mask or his hood. It was warmer night than usual so you wore a pair of skinny jeans with black knee high boots and your orange hoodie. You put on your ear band to keep your ears warm and a pair of gloves. You met Hoodie outside your door and the two of you started your walk. The frost on the trees glowed from the moonlight as you were walking along a path in the woods. Hoodie had his arm around your waist protectively which you didn't mind. It kept you warm and it was sweet. After a while you could feel your legs becoming cold and you became tired. Checking your phone for the time you saw that it was around 1:00 am. Hoodie stopped and you yawned which made Hoodie blush. He thought that it was so cute to see you tired like this. You looked up at him and he leaned down to kiss your forehead, then picked you up bridal style and began to walk home. You snuggled into his chest and as you were about to drift off to sleep you mumbled "Best date ever."
~Ben~
Ben thought that it would be nice to wake you up at 7:00 am on a Saturday to bring you shopping. You were peacefully snuggled up in your warm blankets dreaming about Sebastian from black butler when you felt the air knocked out of you. Waking up and trying to breath again you saw Ben lying on top of you...Literally. "Beeeeeen!" You groaned and opened your eyes to be met with a pair blue orbs. You pushed the boy off of you and looked at him. It looked like Ben just with blue eyes. He was wearing a green shirt with black skinny jeans and some black and white converses. And to top it off he had a green beanie. "Ben? what's with your eyes." You sleepily asked. "Well, people will freak out if they see me with my red eyes so I'm in human form right now. Now hurry up and get ready... We're going shopping." You stuck your tongue out at him and rolled out of bed. Shoving him out the door you went to your closet to get dressed. You picked out a pair of dark green skinny jeans and your black flats with a Legend of Zelda shirt. To finish off your look you put your hair into a side braid and put some mascara on. Looking at yourself in the mirror you yawned. "It's too damn early to be up on a Saturday." You muttered. You exited your room and went to tell your mom that you were leaving to go shopping with a friend. At the end of the day you had 1 bag from American Eagle, 1 from wet seal, and 4 from Hot Topic. As you were exiting the mall you grabbed Ben's hand and kissed him on the cheek. You both left happily.
~Jeff~
"Pssst, (Y/N)... Wake up." You heard from your dream. "(Y/N)... (Y/N) wake up or I'll pour water on you." You opened your eyes to see Jeff staring at you and you held back a scream but jumped too far away and ended up on the floor. "You dip wad! It's 2:00 in the morning! I was sleeping peacefully finally." You snapped as you continued laying there on the floor. Jeff started chuckling and went to your closet and brought out your red hoodie and a pair of jeans. "Get changed, we're going on our date." You glared at him and huffed. "Next time give me a heads up would ya?" You said as you shoved him roughly out of your room and got changed. You put your hair up in a ponytail and put on your black combat boots. "Jeff, you can come in." You said and laid back down on your bed. You heard the door open and close and footsteps come towards you. "Let's go!" He said before grabbing your hand and dragging you out the window. Turns out that Jeff's idea of a date was helping you kill. At first you didn't want to, you were scared that the police would find someway of knowing that you killed and they would come for you. "(Y/N) just one family? Please?" He begged. You sighed and realized that the only way for you to get back into your warm comfy bed was to do it. You grabbed his knife as he lifted you up into the window. You pulled your hood over your head to hide your face and looked around the room. It was bright orange and you saw a teenage girl sleeping in her bed. Jeff entered the room. but went to the corner in the shadows to watch you work. You sighed and gently woke the girl up. Placing a hand over her mouth so she wouldn't scream you smiled. She started to cry and you slid the flat side of the knife along her cheek. "Shhh, don't cry. You look better with a smile." And with that you slid the knife along her throat. To finish it off you cut a smile onto her face. Jeff came out from the shadows and hugged you from behind and kissed you cheek. "Beautiful work." You sighed and yawned. "How many are here?" You asked after yawning. "Well this girl, her parents, and a boy." You nodded your head and walked out of the room. "Let's get this done with." He chuckled and watched as you did the same thing to the rest of the family. "You need a name..." Jeff said as you were walking back to your house. You thought about it and smiled. "How about Sadistic Smile?" Jeff's smile got even wider than you thought possible and pulled you close to him. "Perfect."
~Liu~
Liu and Sully couldn't make up their minds what to do. "Let's go out to eat." "No, let's go to a movie!" Sully fired back. You sat on the couch reading a book while the two argued with each other. Finally you put in your opinion. "How about both?" You asked. Liu looked at you and smiled. "Good idea (y/n)!" *"Now where do you want to go?"* Sully asked you. You shrugged your shoulders and went upstairs to get ready. You guys ended up going to Applebee's for dinner and then to the movie theater to see (Insert movie). When you got home it was pretty late so you kissed Liu's cheek and went upstairs to your room to get ready for bed.
~Toby~
Toby bought had bought you a new pair of brown gloves. You smiled and put them on with your coat and grabbed his hand. "Come on Toby! Lets go take a walk in the park!" He laughed at your childish behavior and ran to the park with you. You two walked along the trail that was at the park and then sat on the swings at the park. A little girl with yellow blonde hair in curly pigtails and green eyes came up to you two and smiled brightly. She looked maybe about 6 or 7. "Are you two boyfriend and girlfriend?" She asked innocently. You felt a blush come to your cheeks and nodded your head. The girl giggled and said "You two are a really cute together! I can't wait until I have a boyfriend!" She said excitedly. You smiled ad said "Well, when you get a boyfriend he will be very lucky to have such a cute and sweet girl like you!" She giggled and a voice called out. "Elizabeth, time to go!" She poured but then smiled and waved to the two of you. "Bye!" You and Toby waved back and smiled as she ran to a woman wearing all red and red hair and a boy with raven black hair and blue eyes. (Guess the anime😛) "She was sweet." Toby pointed out. You smiled at the thought of the girl's excitement of having a boyfriend. After a while of talking you and Toby went back to your house to have some pancakes.
~Slenderman~
Slenderman told you to meet up with him in your usual spot but to dress nicely. You were wearing a black dress with a gold belt on it. You had your hair curled and some makeup on. Putting on your heels and a coat you went to the river. It was chilly tonight so you walked fast in hopes to keep your legs warm. You reached the river to see a tall man there. He was wearing a black dress shirt with a gold tie and black dress pants and black dress shoes. From what you saw he had short silver hair. You stepped on a twig and when the man heard the snap, he spun around. You gasped at his piercing blue/silver eyes. "Ahh, (y/n), you made it!" The man purred. You couldn't speak as he came closer to you. "S-Slender?" He chuckled at your cuteness and pulled you in close. "Yes darling?" He held out his arm to your and you took it. He then teleported the two of you to a fancy restaurant. You guys talked and laughed. When it was time to head home he teleported the two of you back to your house. Taking off your coat you hung it up and smiled up at him. "Thank you Slenderman, I had an amazing time tonight." He returned your smile and kissed your knuckles. You blushed and returned his kiss on his cheek. You giggled at the blush that slowly mad it's way to his cheeks.
~Red~
You were looking through your closet for a hat to go with your outfit. You were wearing a black flowing dress that went below your knees and a vest that looked like Red's but more feminine. You were wearing black and white converses as well. You wanted a hat that would look like Red's but you couldn't find one. Sighing with defeat you backed out of your closet and looked around your room. You went over and brushed your hair and put some make up on before Red arrived. Taking one last look in the mirror, you went into your living room and started playing pokemon. Your GBC started to shake so you put it on the ground and waited for Red to come. He came and took your hand and dragged you into Pokemon. "Ahh Red a little warning next time!" You exclaimed when you opened your eyes. He chuckled nervously and muttered an apology. He then took your hand and the two of you started to walk around the town you were in. At one shop they were selling hats and you saw one that looked like Red's and dragged him over to it. "Red! I need that hat! You said while pointing to the hat. Red looked at you and grabbed the hat and paid for it. He put it on you and you twirled around. "Yes! I got it!" He laughed and the two of you continued your shopping.
~Silver~
"S-Silver... Where are we?" You asked Silver as the two of you went by a pokemon cemetery. He looked at you and noticed you staring at the cemetery. He stopped and pulled you into a hug. "I-It's OK (Y/N)." You let a tear go and nodded your head in his shoulder. After settling down you two started walking again. After a while of walking you two came to a tower. Silver held your hand as the two of you started walking into it. Once you were at the top and looked at the sight it took your breath away. It was beautiful. After the tower Silver took you to town and you went shopping. It was getting late and you were getting tired so Silver took you back home. You didn't want Silver to go once you got back. You put your new cloths and anything that you bought away and when you turned around Silver was sitting on your bed. "Silver, can you stay here while I go change?" You asked him. He nodded his head and you saw a small blush appear on his cheeks. You left to go to the bathroom. You brushed you teeth and changed into a tank top and short shorts. When you got back into your room Silver looked at you and his face turned red. "Silver, can you stay with me as until I fall asleep?" You asked him innocently. He nodded and you fell asleep in his chest. "Silver, thank you for an amazing date today."
~Sonic~
For a cocky douche bag Sonic was really nervous. He didn't know what to do or what to say. You two were walking in the woods with an uncomfortable silence between you. You were thinking of something to say that could hopefully cut through the silence but nothing was good enough. Finally an idea came to you mind. You smirked evilly and poked his arm and when he looked at you, you slapped his face. His eyes widened in surprise but then narrowed into a glare. You laughed and started to run away from him. Of course even in human form he was faster than you and easily caught up with you. He lifted you up from the ground and started carrying you bridal style. You wrapped your arms around his neck and buried your face into his shoulder. After a while of running he slowed down and looked down at you. Your eyes were closed and you had a smile on your face. He leaned down and gently kissed your forehead. You opened your eyes and met with his blue ones and you smirked. "There's my cocky son of a bitch!" You said and he chuckled. "Careful, I might just drop you." You tightened your grip around his neck and he started to walk back to your house with you in his arms.
~Dark~
You were sitting on your couch in a black tank top with a white skull on it and a black skirt with a pair of black and white vans on. Why you ask? Dark had said that he was going to take you out today and he would be arriving any minute now. Suddenly he popped out of your screen and you jumped in surprise. "Ready to go?" He asked as he came fully out of the screen. You jumped off the couch and grabbed his hand. "Sow where are we going?" You asked excitedly. He smiled and put a blindfold over your eyes. "It's a secret. And by the way, you look really cute." You blushed and put your hair behind your hair. "Thank you." Your felt yourself be lifted off the ground and then a weird feeling go through your body. It felt like needles were poking you everywhere. Your grip on Dark's shoulders tightened and he whispered in your ear "Hold on, just a little longer." You nodded your head and loosened the grip. Dark set you down and took off the blindfold. You opened your eyes Nd they widened. You smiled widely and took in the sight around you. You turned around to Dark but you gasped at him. Instead of looking like Dark Link, he looked human. He had black hair, tan skin, and dark brown eyes. He was wearing a black muscle shirt and black skinny jeans with a pair of black converse. You stared and started to blush at him. He smirked and moved closer to you. "Like what you see (Y/N)?" You looked away and went back to looking at the scenery. "N-No..." He walked next to you and grabbed your hand and started leading you around the game. It was about sunset by the time you guys were done exploring and you had one last thing you wanted to see. "Hey Dark... Can you do something for me?" He looked down at you and nodded. "Can we find Link?" He narrowed his eyes and huffed in annoyance. "Come on, he's usually this way." You smiled and the two of you went to find Link. "If you kill him, he comes back to life right?" He nodded and the two of you kept walking in silence until you found him. Link saw you and Dark and stood up from where he was sitting. "Here." Dark said annoyed. You smirked evilly and whispered in his ear "Can you kill him? I want to see you fight!" Dark's eyes opened in surprise and then he smiled evilly. "Anything for my princess." He took his sword out and he and Link started to fight. You watched in amazement at how Dark fought and when he finished with a blow to Link's chest you ran up to him and hugged him. "That was amazing! You have to teach me sometime!" You looked up to the sky to see it was now dark and Dark took your hand and brought you back home.
~Laughing~
Laughing appeared at your bedroom door in his human form. You were reading a book on your bed when a boy that looked about 21 opened your door. He had black hair and blue eyes. He was wearing a black polo shirt and dark blue skinny jeans. "Ummm... Who are you and why are you in my house?" He laughed a laugh that sounded a lot like L.J's laugh. "L.J is that you!" He laughed again and said "Lollipop don't you recognize me?" You shook your head and walked up to him. "Holy crap. You're hot!" You blushed and he laughed. "Come on, we have to get going!" He said and you gave him a confused look. "Where are we going?" You asked him. He grabbed your hand and you found yourself in a movie theater. "What?" "We're going on our date." You nodded your head and he left to go get some food and soda pop. He came back and you snuggled into his chest while you watched the movie. You didn't know that it was a horror movie so whenever there was a scary part you would bury yourself into his chest. After the movie you two went to a candy shop and bought some candy and then went home. You sat on your couch talking and eating candy. Over all it was an awesome date.
~Percy~
You and Percy decided to go out and get frozen yogurt. You wore a light blue v-neck shirt with a pair of skinny jeans and black flats. Your hair was flattened and your wore neutral color makeup. Percy would be over any minute now so all you had to do was wait. A knock on your door came and you answered it. There a guy stood, he had red hair, dark brown eyes, very good looking, and looked to be about Percy's height. He was wearing a white t-shirt and a dark blue zip up hoodie unzipped, dark blue jeans and a pair of black vans. "Hey (Y/N)!" He said. It sounded like Percy and your eyes widened. "P-Percy?" You asked and he nodded is head. "Holy crap..." He smiled and gave a small chuckle. "You look pretty." You muttered your thanks and he grabbed your hands. "Come on, let's get going." By the time you guys reached the the frozen yogurt shop, you were over the shock and blushed. "Something wrong (Y/N)?" Percy asked once he saw your heated face. "N-No... it's nothing." He nodded and the two of you continued your date. Minus the fact the he kept looking at you and you would blush, it was a fantastic date.