Sleepover Headcanons
MINORS DNI!!!
Context: Characters mentioned below with a gender-neutral reader during a sleepover
Content/warnings: implied non-consensual drugging(scarecrow's fear toxin to the reader), alcoholic beverages consumed, baking, sleepover activities, stealing(as a crime and not like stealing someone's food), intellectual debates and competitive gaming and platonic
Riddler (Zero Year)
Sleepover? More like a competition for anything ever!
He's actually quite the video game nerd, so when he finds out you play video games...
Well, the whole night will be spent playing against each other, round after round
Eventually, it gets to a point where you are just losing game after game, and then Riddler decides to spare you any further embarrassment
Riddler (Arkham Knight)
sleepover? No no no... this is a watch Riddler work kind of sleepover
Will ignore you and your desperate pleas, even if you try to tempt him with popcorn and horror movies
Eventually, he's had enough of your begging; it's far too distracting
You use the sleepover to essentially make it a form of self-care on his self-care-deprived self
eating, skincare, resting, he doesn't realize until you've put a face mask on him
Will attempt to get back to his work, but in the end, he succumbs to your kindness
He does not fall asleep until 4 am, but most of that time was spent unwinding by attacking villagers in Minecraft and accidentally 'hitting' your character when you were on half a heart
Riddler(Deathstroke Defiance 2016 #25)
One thing is for sure: you two are going to play a very intense game of Uno
Fights will occur, and feelings will get hurt
The two of you will place bets, and because it’s a game of chance, Riddler could actually lose
When he does lose a game, he gets cranky and starts adding rules in his favour, but that fails
Pillow fights occur because surely he can beat you at that, right?
After an hour, you two would get bored and probably talk very passionately about your interests for hours on end before you both fall asleep
Killian (spies in disguise)
After you pester him to join, he's doing so with the least amount of interest
He's barely paying attention to the movie; he doesn't even touch the snacks, and frankly, he's more interested in silently judging you and your pjs
He's only entertaining this whole thing because he can't fall asleep, and your ranting about the movie might actually help him fall asleep from how boring it is
Occasionally, he will speak, although it's mainly questions or judgmental comments about the movie
Lance Sterling (Spies in Disguise)
He knows a thing or two about sleepovers, and he knows how to throw one
Because he's the social butterfly, the sleepover is much more fun than just two people
You will be wide awake the entire time with many fun shenanigans and snacks
Plus, his house is like AMAZING and HUGEEE to play hide and seek in, despite how childish the idea may seem, it's actually really fun when you have a 1000 hiding spots
He curates the night to actually be quite memorable and fun with all the activities!
He Cheng (19 Days)
He's not interested at all; he's far too busy to do something like that
He would just make one of his men participate in his place
That is, until he can't fall asleep because you and his men are being loud
He walks by the living room near midnight to see you and his men clearly baking cookies near midnight
He decides then to watch at least, and then take a finished cookie just to 'make sure' they came out right and weren't poisoned or anything
After that, he will make everyone go to bed; it's too late for him to be smelling cookies when he's trying to sleep
Darkness (Legend 1985)
He finds the idea silly, such a childish human thing to do
It does not mean he won't entertain it, though, and to great lengths
If you were to have a 'sleepover', it would be a very luxurious one
He would particularly be interested in picking your brain about what a ‘human sleepover’ is
What movies, what activities and comparing them to his own idea of one
He would enjoy late-night talks with you and engage in very long, meaningful conversations about pretty much anything with you
Le Chffire (Casino Royale)
He wouldn’t be there in the first place but if he were, he’d be bored
No he does not want to watch a movie and he’s TIRED
So yes, he will unwind but not in your way(unless his way is your way)
Besides, he doesn’t need to stay up more than he usually does, he loses enough sleep already
So, during the time he doesn’t feel sleepy, he supposes he can teach you a thing or two about poker
Why not throw in a few drinks while he’s at it to liven things up
In fact, maybe have some dark chocolate-covered strawberries by as he teaches you
After all learning poker is a hard skill
Steven Obanno (Casino Royale)
Will subject you to many deep and even philosophical talks
A few hours go by, and you two have practically talked about every single thing ever, and the snacks aren’t even touched
Will bring up the philosophical ship of Theseus paradox
Many arguments and passionate intellectual debates will happen throughout the night, and you may or may not start pillow-fighting over your arguments about hypothetical situations
Eventually, the two of you are over it, tired and lying down, feeling all giggly at your own squabbles
Will settle down with some tea before finally falling asleep
Tuco Salamanca (Breaking Bad)
He would be down
although he might mistake a sleepover for something more wilder
Whatever peaceful yet fun night you had planned, Tuco replaced it all with more adventurous and exciting activities
Turns out, Tuco knows how to have fun when it's not about creatively hurting people!
You two will still do a few of the activities you had planned, but he just makes it so much more fun
Although it does end in Lalo being awoken by how loud Tuco and you were both laughing when you showed each other your attempts at drawing each other
Black Mask (general)
A slumber party is fine… although it would be alot more fun if he changed it up a bit
Since the goal is to stay awake… why not play a few games
Its a lot easier to stay awake when your hiding in god knows where as he’s trying to find you
Or when he found you and your running all over the place before he catches you
Twister sounds a lot more fun at 2am compared to 9 am….
Once you two are tired out only then you two will probably watch a movie although you both wouldn’t know how it ended because you both fell asleep
Uvogin (Hunter x Hunter)
Who was he to say no to a sleepover?
You brought beer? Even better! Now he doesn't have to steal it from some random grocery store :)
Hope you don't mind, he brought ice cream!
Will expect you to have some sort of activities planned after all, you invited him over
But the second you put on a movie hes bored out of his mind and he makes it very clear he is not interested in watching some boring movie
But if you run out of activities because he was far too bored for nearly all, he doesn't mind basking in silence or just silly dilly dallying around with you
Might try to drag you out for some late-night stealing, after all, a sleepover doesn't mean it has to be STRICTLY in the home, right? At least to him, he thinks that
Scarecrow (Dark Knight Trilogy)
He may or may not treat you like a test subject for his fear toxin
Will play along until you fall asleep
He's not interested at all, though and the only reason he'd say yes is to treat you like a test subject without your knowledge
Have fun having nightmares though
Unless he doesn’t see you as just some test subject, he would probably participate with mild interest










