Jeff:
You had gotten asked on a date by Jeff and now your getting ready. You put on your black leggings and a white dress. You put on a cream cardigan and some black Ugg boots. You grabbed your shades and put them on. You smiled in the mirror and grabbed your phone. You walked down the stairs and saw Jeff standing there in his usual outfit. Except the hoodie didn't have blood on it. You weren't going out in public so he didn't have to hide his smile. You handed him some shades and he looked at you "Why do I need shades?" He asked. "So you don't get noticed by my neighbors." You said. He nodded and put them on. You walked out of the house and waved politely at your neighbors. They smiled and waved back. You and Jeff walked out back to the woods and he grabbed your hand. He laced your fingers and you smiled at him. You two walked around the woods and you sat down on a rock. Jeff took off his shades and his head snapped to the side. "I'll be right back babe. We have an intruder." He said quietly. You nodded and he stalked off. You say there for a while until your felt something cover your mouth. "Hello sweetie. What are you doing here all alone?" You heard. Tears poured down your face. The person turned you around and you saw someone that looked like slender. "I'm offenderman. A-" "Get. Your. Hands. Off. My. Girl." You heard Jeff say through gritted teeth. The man let you go and you scrambled over to Jeff. He pushed you behind him and you hid. "I would hate to kill the brother of slender but if you hurt her I will." Jeff threatened. "Sorry Jeff." Offender said. "You should be. You ruined our date." Jeff snapped. "Well you left her alone." Offender said. "Well I had to take care of an intruder." Jeff said. "What? I thought I got them all?" Offender said. "Except one." Jeff said. "Alright I'll leave and let you two get back to your date." Offender said. You two nodded and he left. Jeff turned around and checked you. "He didn't hurt you did he?" He asked concerned. "No he didn't. Thank you." You said hugging him tightly. He breathed a sigh of relief and hugged you back. For the rest of the day you two stayed at your house until your parents came home.
Slenderman:
"Hey Y/N? Wanna go on a date?" Slender asked. "As long as offender doesn't ruin it. I heard he tried to kill Jeff's girlfriend yesterday." You said. "I had a talk with him about that. Jeff came home steaming yesterday because of it." Slender said. "Hey I didn't know okay!?" You heard. You laughed and hugged slender. "Of course." You said. So you and him left and you helped him put up his notes for his victims. After you put up the last one you heard a scream then silence. You smiled when slender came back. He had something behind him. "Whatcha got there?" You asked. He moved his hands and held up a head. Your eyes widened then you started laughing when you saw it was your worst enemy. "She shouldn't have been walking in the woods should she have?" He asked. "Nope. Karmas a bitch Huh Chloe?" (If your name is Chloe change it.) you asked the head. Slender laughed and threw the head far away from us. Slender picked you up and threw you on his back. You shrieked and giggled. He started running really fast and you laughed like a maniac.
BEN:
For your ideal date it would include; cuddling, eating food, playing video games and laughing. That was what happened on your first date with BEN. You were sat on your bed in between his legs while playing Mario kart. You were winning and BEN was freaking out. At the last minute he passed you and got in first place. You groaned then laughed as BEN jumped up and did a victory dance. He stopped and got back on the bed. He layed you down and you two cuddled until you heard you front door open. BEN kissed your cheek and jumped into your tv as your door opened.
Hoodie:
Hoodie asked you to meet him in the park by your tree for a date. So you got dressed in black leggings, a white dress and a cream cardigan. You grabbed you sunglasses and your phone and walked out of your house. You were passing the road when you heard a horn blaring. You froze in your spot then felt someone tackle you out of the way. Your heart was beating out of your chest as the tears poured down your face. You looked at you savior and saw hoodie. You hugged him tightly and he hugged you tighter, scared to lose you. For the rest of the day he held you in his arms as you sat there in shock from almost dying. No words were spoken. He kept kissing your cheek, forehead and top of your head to comfort you.
Masky:
You and Masky were at the bakery that you worked at on your day off for a date. You smiled at your best friend Y/BF/N at the counter. "Y/N! What can I get you?" She shrieked. "Can I get a chocolate drizzle cheesecake slice please boo?" You asked sweetly. "Of course boo. And what about your friend here?" She asked talking about masky. She knows him so she doesn't mind his mask. "May I get a strawberry cheesecake please?" He asked. "Sure thing Masky." She smiled. She gave you your slice and gave Masky two. You went to a booth and sat down. You happily ate your slice and Masky happily ate his two slices. You both talked about nonsense and laughed a lot. When you finished you both waved bye to Y/BF/N and walked out.
Toby:
You and Toby were just sitting on your couch watching movies as a first date. "What do you wanna watch next?" He asked. "You." You said. He blushed slightly and you giggled. You layed down on the couch and Toby layed down next to you. You both were cuddling and talking. "Y/N?" He asked. "Yes Toby?" You asked. "What do you call a red headed ninja?" He asked. "I don't know. What?" You asked smiling at him. "Ginja." He said. You giggled and cuddled closer to him. "I love you Y/N." He whispered. You smiled. "I love you more Toby." You said. "Not possible." He argued. "Yes possible." You smirked. "Nope." He said. "Yep." You said. "Nope." "Yep." "No." "Yes." "Yes." "No. Wait!" You said but he was laughing. You groaned then laughed with him.
Silver:
Silver took you into the Pokemon world for your first date. "H-Hey Y-Y/N? C-C-Can I a-ask you so-something?" He asked. "You just did but go ahead." You smiled. He blushed. "D-D-Do y-you l-l-love me?" He asked blushing. "Of course I do silver. How could I not? Your sweet, cute, shy and amazing." You smiled. He blushed more. "I-I'm a k-killer." He said. "I know but I still love you. Nothing can ever change that." You assured him. He smiled and kissed your cheek. You blushed and hugged him.
Red:
You and Red just lounged around the house all day. Cuddling, talking, playing games and laughing. "Hey Red?" You asked. "Yea babe?" He asked. "What's it like being a killer?" You asked. "Wanna find out?" He asked. You thought about it. Then shook your head. "I don't think I'm ready yet." You said. "Well we can wait til you are but I'm not gonna tell you what it's like. You'll have to find out when your ready." He smiled. You smiled back and nodded then you two went back to playing COD Black Ops.