Author's Note: I've decided to continue, but without Slenderman's bit. It may be added back in eventually, but I doubt it.
Jeff the Killer
You hadn't talked to, nor seen, Jeff since he met your now ex-boyfriend. You were grateful for this and were finally able to moved on with your life. You lived in an apartment, which was shared with a roommate who almost never slept there. Your life was pretty great at the moment because you single and getting relatively good grades in college.
That aside, today was your 21st birthday and your friends had taken you to a club. You danced a little, but mostly sat at the table sipping on some sort of alcoholic beverage.
While your friends were dancing, you heard an all too familiar voice, "Hey, Y/N... You look good..."
Jeff... That son of a-
You ignored your conscience as you turned to face the boy in the white hoodie, "Can I help you, Jeff?"
"I just came to ask to we could catch up sometime... Not like a date, but just as friends," Jeff fidgeted with his hands, "It could be a date... If you wanted..."
"I'm busy with school and stuff... I'm not really interested in having a relationship or a friendship with you," You shrugged.
"Please? I've given you enough time to cool off... I'm still in love with you," Jeff sighed, glancing at the ground.
You gave Jeff a once over, realizing he looked like he had gotten very little sleep these passed few years and he'd also thinned out a bit. You frowned, "Fine... It can be a date... But only this once."
Jeff nodded, "I understand... So if this is a one time date, can we start it tonight and finish it another time?"
You raised an eyebrow, "What do you mean?"
"Someone needs to teach you how to drink right," Jeff smiled a bit wider.
*********
Eyeless Jack
Jack had been lounging at Slenderman's house for the last few years. He'd been in a depression ever since he found out about your now ex-boyfriend. Slenderman was sick of it so he kicked Jack out and made him go find someone to steal kidneys from.
Jack was so depressed, he couldn't even hunt. He ended up just going to your old house and knocked on the door.
Your mother (A/N: If you don't have a mom, just say dad), "Uh..." She didn't know how to react to this guy who was leaking black stuff from under his mask without any eyes.
"I'm Jack... Is Y/N?" Jack asked.
"Uh... Oh, yeah... She's home for a birthday party. Are you a guest?" Your mother asked curiously.
"Um... Yeah!" Jack nodded. Your mother smiled and pulled him inside. You were just opening gifts when you noticed Jack.
"What the hell-"
"Shh... Y/N... I'll make this brief. I miss you... A lot... A crap load... A shit ton... Happy birthday, but I can't take being away from you another year... Please... Take me back," Jack pleaded.
You hummed, "Mmm... Fine... You have one date to prove that you're worth wasting more time on."
*********
Laughing Jack
L.J knew it was your 21st birthday and decided to send you some candies. He sent you the type of candy he'd given you when you first met. He just left it on your doorstep and left without knocking or anything. He left no note, or so it appeared.
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Creepypasta Boyfriend Scenarios
FanfictionYou are the girlfriend to one of the Creepypasta guys (Or all, you decide) *Requests accepted whether big or small!*