Chapter 1: Jeff the Killer
Chapter Text
-Jeff's eyes became very infected after he burned his eyelids since he couldn't blink, which caused him to lose his vision completely. But after he became a proxy, his vision was cured for the simple reason that he would be of no use to Slenderman while blind. Now he can live normally without his eyelids without it affecting him at all.
-On the same note, since he can’t close his eyes, he uses a sleeping mask to cover them when he goes to sleep. Its a pink one with “sleeping beauty” written on it in cursive.
-Jeff is very musically inclined. He can play the drums, electric guitar, and piano. He’s also a very good singer but he’d prefer to keep that last fact to himself.
-He is terrified of spiders, specially the big ones. Sometimes Ben will hack his computer and flash an image of a spider when he’s watching porn to freak the hell out of him. He let out a scream every single time.
-He has a sense of childish fear whenever people call him by his full first name, like when a child is caught doing something they know they weren’t supposed to be doing and now have to face the consequences of their actions. That fear skyrockets if the surname is added in.
-Very feel people in the mansion actually like him other than Toby, Sally, and Ben. Everyone else thinks he’s a self obsessed, arrogant, obnoxious asshole who can’t keep his mouth shut. He pretends it doesn’t affect him.
-Jeff is a big ol’ narcissist, he needs all people around him to love and adore him like he’s some kind of deity, yet he doesn’t do anything to change his behavior or make himself likable at all and still thinks he’s in the right to be mad when people are rude to him.
-His hair fell out completely after he was set on fire, but it grew back within a few months. However, now it's much thinner and more fragile than it was before, and he has a permanent bald patch on the burned half of his head.
-Speaking off, his left eyebrow also fell out in the process and now it doesn't grow anymore, so he just draws it on because he hates how asymmetrical his face looks with only one brow.
-Jeff can’t accept the fact that Nina has grown out of her obsession and moved on. In his mind, she’s still obsessed with him, she’s just trying to convince herself that she isn’t. He hated her as a person and hated her clinginess, but he loved knowing there was someone that crazy for him and willing to do anything for him.
-He tried going after her to try and manipulate her into coming back to him, but all it resulted in was a knife thrown at his head and Jeff rushing back to the mansion with his tail between his legs. That didn’t stopped him from trying multiple times after the first one.
Chapter 2: Ticci Toby
Notes:
This chapter is a little shorter, but don't worry, I have more headcanons for Toby and several other characters that I intend to post, just be patient.
The next chapter will probably be my take on some characters' relationships, and I plan to post it very soon, so stay tuned.
Also, you guys are free to make requests, just comment what you’d like to see next!
UPTADE: I know I said I would post again soon, but I lied. I have decided to keep working on a bigger project that I’ve been working on for almost two years that I had given up on, but thanks to my friend, I decided to continue writing it, so as for now, that’s my main focus. Thank you so so much for all the kudos, it means a lot to me, specially considering this is my first work, and thank y’all for reading!
Chapter Text
-Toby is not the brightest bulb in the box, but he isn’t nearly as stupid as people make him out to be. They act as if he can’t understand the things they talk about or take care of himself properly, even though he very much can, and he hates it.
-Like Jeff, not many people in the mansion like him. He is tolerated at best as, due to his mental health issues, sometimes he can’t be blamed, but he’s still seen as someone who’s unpredictable, inconsiderate, and that can’t be trusted.
-His only allies are Kate, Hoodie, Masky, and Jeff, though the two men are not opposed to putting him in his place, and he and Jeff have a rather rocky relationship.
-Toby has a short fuse, violent tendencies and has the nasty habit of blaming everyone but himself, while Jeff is, well, Jeff.
-Even though he can’t feel pain, Toby is deathly afraid of needles. He just hates the sight of it penetrating his skin. He was bitten by a raccoon once, which resulted in him being muzzled, arms and legs tied while Masky and Kate pinned him down so EJ could give him the rabies shot. Not his finest hour.
-He remembers almost nothing about his life before he became a proxy. His memories have holes in them, and all faces are blurred, but he can still recall how they made him feel. Safe, protected. Whoever those people are, he hopes they are okay.
-Like a dragon guarding its hoard, Toby has a collection of trinkets and random stuff he keeps under his bed where no one can see. Among these things are buttons, pebbles, animal bones, things that belonged to his victims that he stole, and a blue sweater. He doesn't remember where this sweater came from, but it's always been with him. It used to smell nostalgic, like lavender and freshly washed clothes, but that scent has faded over time. As silly as that might sound, the sweater is his most valuable possession.

Kostampinos on Chapter 1 Fri 03 Oct 2025 07:34PM UTC
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GUMM1W0RMZ_00 on Chapter 1 Sat 04 Oct 2025 08:04PM UTC
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Kostampinos on Chapter 1 Sat 04 Oct 2025 09:42PM UTC
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GUMM1W0RMZ_00 on Chapter 1 Sun 05 Oct 2025 04:07PM UTC
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Kostampinos on Chapter 1 Thu 09 Oct 2025 07:39AM UTC
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Mark_Beaks_Is_Best_Parrot on Chapter 1 Fri 17 Oct 2025 03:55AM UTC
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GUMM1W0RMZ_00 on Chapter 1 Fri 17 Oct 2025 08:37PM UTC
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