Dating Simon Headcanons

Dating Simon headcanons

If you know me, you know I literally made this account because Tumblr was the only soure of Simon screencaps etc I had. And, since I am writing what I believe to be the first ever Simon x reader fic on the entire internet over on AO3, I thought I’d feed you all some more. So, here’s some headcanons of what I think it’d be like to date Simon. Might also include NSFW if I feel like it/if anything comes to mind, but it will be marked with 🍋(real original, I know) so you can skip it if you want to. It is also currently 2 hours past when I’m supposed to go to bed and I haven’t gotten proper, 8 hours of sleep in like a month so yeah, apologies if there’s any grammar mistakes or anything similar.

They’re all kept gender neutral, and reader is referred to as ’you’.

Specifically book Simon, since book and show are pretty different I now realize

Emjoy.

TELL HIM YOU LOVE HIM AND HE WILL MELT

Ok, sorry, I’ll calm down

But seriously, we know this kid hasn’t really gotten that much love or compassion from others, and probably was never even in a real relationship before you, so whenever you express that you genuinely like him and want to be with him, he kind of schort-circuits

He’s also kind of worried you’re only with him to get info on others, and once you’ve got enough you’ll leave him, and that it’s all a cruel joke

But, again, if you reassure him that no, you’re not just here for info and you do infact love him, he’ll slowly learn to not listen to the voice in his head, it will take a while tho, so get ready

Of course, since it’s Simon, if anyone ever messes with you, in any way shape or form, be that at school, online, strangers in public, whatever, he will have them on display on AboutThat the next morning, or even within a couple of hours, front and center. He doesn’t really care who it is, but if they mess with you, they mess with him too

🍋 Now we all know Simon likes to feel all high and mighty, untouchable, right? So, might I suggest, that Simon would probably enjoy power play? Of course he’s always the one with power, and I feel he’d get a reeeeeeal kick out of getting to use you however we wants (with your consent of course, he might be an ass who kinda ruins peoples lives but he’s not a monster). If you’re into it too then even better! Though he’d never push you too far, he doesn’t want to hurt and maybe even lose you! Call him something like Sir, Mister, Master or anything of the like and wheeeeeew you’ll be in for a ride. Most of the time literally xD

Simon is definitely terrified of losing you, I mean you’re one of, if not the, first people to really care for him. He’s always worried that he’ll say or do something wrong and that you’ll leave him. :( please do reassure him you won’t leave, it will probably end up with him crying, though.

At school, of course, he’s all cocky and confident, but I feel with you, in private, be that at yours or his place, he’d stop being so braggy, and actually be quite touchy and affectionate and quiet. I can imagine you two just sitting on whoever’s house you’re currently in’s bed, both sort of doing your own thing, but still leaning on another, maybe occasionally saying a few words, but mostly keeping quiet. Sometimes the Tv will be on in the background, playing whatever channel was last on, sometimes it’ll just be music, or maybe even nothing, only the sounds of both of you clicking away at laptops, phones, the sound of pages in a book turning, whatever.

I think we can all agree that Simon is probably pretty touch-starved, I mean lookatem! At school he’d probably not be that touchy, maybe just holding your hand or his arm around your waist, just small things people easily miss. He’d probably not be the biggest fan of PDA, but also probably would’t hate it. Sure he’s give you a quick kiss or two, but you wouldn’t get into full on makeout sessions in the middle of school. He hates when others do it, so he also won’t.

In private, however, it’s as if he’s superglued to you, always touching you in some way. Leaning on you when you’re both working, holding you when you watch Tv together, you sitting on his lap when he’s at his desk, whatever. He’s always hesitant to let go because his brain tells him that if he lets go, he’ll never get to hold you again, that you’ll disappear.

Maybe, just maybe, you’d even be enough for him to scrap his plan, to not actually kill himself. I doubt he just one random day decided to do it, he must have started planning ahead years before. And it will take a while for him to decide that no, he doesn’t want to do it anymore, because he has you. I feel the day it’s all officially cancelled, he’d probably sit down on his bed or desk and just, take it all in for a bit. Never had he felt this safe and happy with someone before, so much so that he doesn’t want to kill himself anymore. He definitely cries.

I feel you’d eventually find out. Maybe you do by accident, maybe he tells you, doesn’t really matter. Either way, a lot of crying happens. You crying because he wanted to kill himself, then because you are the reason he didn’t and then him crying because of all the emotions and how new this all is for him.

NEW

So we all probably know the song 'Teenage Dirtbag' right? Well, I just heard it on tiktok, the end part where she also sings to be precise, and I dunno why but I just thought of Simon and his S/O. Like he never thought they'd ever even acknowledge him, and when they do he's just like "Wot". I dunno, my brain just does stuff sometimes.

In conclusion: I fucking love Simon, I want him to be happy, healthy and loved and I will gladly give him that love. <33

If anything else pops into mind, I will add it, I’ll mark it too so you’ll see what’s new!

Watching OOUIL

HEAVY SPOILER WARNING FOR LITERALLY THE ENTIRE SHOW I wrote down anytime I had important/sudden thoughts about stuff. Little warning, there is quite a lot of times I just simp over Simon, but what's new? There will be timestamps so you can go and look what happened to cause that reaction. Also since I was watching in one sitting and it was already past midnight and I was recovering from fever and tired and all that good stuff, towards the end and the last few episodes I didn't write down much. That is also the reason for the many, many typos xD I apologize

Episode 1

00:10 > literally just hearing Simon’s voice is already doing smth to me xD

00:22 > Simon honey I love you but that jacket was a CHOICE

00:50 > not the “I ship it” comment qwq

01:09 > god bronwyn's parents suck

01:26 > I only have my headphones on one ear and like Simon keeps talking and I never want him to stop xD

01:31 > Ah yes, the classic “ew our parents are kissing” teenager trope. just suck it up, Maeve

01:42 > i know, i know, i'm just being nitpicky, but Bronwyn’s phone says she had headphones connected? no she doesn’t

01:52 > if you ever see me smiling that wide while running, please assume I’ve been possessed, I probably have

02:02 > oh my god i can FEEL the sand in Copper’s shoes qwq

02:12 > Wildcats? isn't that like also a meme? like “What team? Wildcats!” idk I’ve only seen it a handful of times

02:46 > even if i hadnt read the book/had no idea what happens I’d still 100% know Cooper’s dad is gonna be an ass

03:21 > Addy is like, so naturally pretty qwq Girlie you don’t have to do all of this qwq I just wanna give her a hug man. And a gun so she can get rid of Jake. I’d help her hide the body too. Sorry, got a lil too into it there xD

03:28 > her outfit is soooo pretty tho I mean c’mon

03:44 > A bad love story? Like a… BAD ROMANCE?

03:47 > “Varsity skank squad” Damn Simon! Really going in on Addy, huh?

03:56 > the “well, you know” should NOT have affected me as much as it did xD

04:08 > Addy, remember that gun I talked about? Yeah, use it on your mom too while you’re at it

04:18 > god Jake is ugly. I’l sorry to any fans of his actor but damn. it really do be the basic white bois huh?

04:23 > you can see how uncomfy Addy is qwq

04:41 > “we’ll be quick” we get it, jake, you don’t last long

05:07 > TJ looks wise? no thanks. TJ being a dumbass? bonus points

05:10 > why does that chick look almost identical to Addy?

05:22 > Everyone wants to fuck a bad boy? Honey I want you. I mean if Simon isn’t a bad boy then what is he?

05:29 > “I’ve got so much dirt his probation officer is gonna bury him in it”? Simoooon, look at you with the metaphores

05:44 > Run bitch, ruuuuun! Or alternatively, “I’m fast as fuck boie!”

06:12 > God how I wish I was Janae right now……

06:17 > My god that shirt has a vneck… don’t be shy, take off the tshirt underneath…

06:39 > Lesbians?? In my tv show?? Fuuuck yeeeah!

06:45 > oh my god he’s wearing an earring… Quick, what’s the gay earring rule again? “Right ear means gay, eft means not gay but expressing feminine side” You heard it here first, folks, Simon is a secret Femboy xD

06:46 > these slowmo shottssssss I am living

07:16 > Simon, honey, that is such a bad idea to just have AboutThat open to anyone who flips open your laptop! C’mon, I thought you were smarter than this

07:21 > I would be looking at him the exact same way, Janae. 

07:27 > The smirk,??????? HELLO?????

07:42 > I’ve said it a lot and i will 100% say it again, but DAMN Simon is just so pretty qwq Perfect actor choice 10/10

07:44 > “She can’t prove it’s me” This school probably has security cameras, yes she’d know it’s you. But then again, if the school did have cameras, they’d have solved the mystery waaaay quicker.

07:49 > I am never going to emotionally recover from this

08:19 > he literally has “cold blue eyes” like in the book and that’s what made me immediately fall for him in the first place!!!!

08:23 > What the fuuuuuuuck :0

08:39 > “There is is… that damn smile”

08:45 > Love that she wrote Avengers but from what I can see they’re all DC. Great job, teach

09:17 > Just noticed Bronwyn’s necklace and damn is it ugly

10:02 > Bronwyn never did make it to Debate…

10:16 > no but why is that kinda cute? the way he’s tilting his body like a kid qwq

10:19 > :0 this is where the book starts!! THE COLD BLUE EYESSSSS

10:32 > Is Simon…. shorter than Bronwyn? Or is it just her shoes?? omg is he shmol qwq

11:02 > The way hes sitting, twiddling his fingers, I just, I’m dying

11:05 > then again, there’s probably a lot going through his head, isn’t there?

11:16 > Bronwyn please just stfu. Avery will not believe you. I know, cuz I’ve read the book

11:27 > Isn’t Bronwyn supposed to be the smart kid? Cuz that wasn’t that smart

11:40 > I love his personalityyyyy so sassy

12:25 > he knew she’d say that… he knew… 

12:33 > You can see it on his face qwq I hate this qwq

12:49 > Eggs instead of a carcrash? Weird choice but ok

13:17 > I mean he probably doesn’t have one so xD

13:18 > Nooooooo, he drank iiiitttt qwq

13:31 > It’s taking this long? How? Shouldn’t it happen immediately? Or is that cuz of the amount of water?

13:56 > Nooooooooooooooo qwq I can’t watch this, I’m just gonna start crying qwq

15:48 > I skipped ahead, I couldn’t watch that qwq Reading it is way easier than seeing it

15:54 > my god jake looks ridiculous xD

16:06 > Looked like he was dead? Honey he is!

16:27 > Keely is so pretty qwq

16:56 > They could 100% pass for a straight couple it’s wild

17:07 > Florence and the machine? Like FFXV Florence and the machine? :0000

17:17 > pffffff

17:41 > Bruh does she look okay? She just witnessed her classmate dying! She probably isn’t!

18:09 > He also has an earring?? dafuq

18:53 > Yeah it was!! Wait til you find out the backstory to it

19:00 > his side profile xDDD

19:15 > you can see the tension between hem, god damn

19:32 > Simon’s baaaaaag :0

20:28 > is he getting suspicious??

20:47 > how does her mother know? she a doctor or smth?

21:01 > god that “Bayview High School” could not look any faker xD

21:11 > Janaaaeeee qwq she needs a hug just as much as I do rn qwq

21:24 > The deathstareeeeeee :0 Janae

21:31 > Reading the book I never cared much for Janae, but actually seeing her so fucking sad and close to tears? It’s hitting

22:10 > QWQ I AM GOING TO CRY

23:32 > “Trauma bonding with Nate” I don’t even know this person’s name but I like their humor xD

26:41 > There is no way in hell they both look at eachother at the same time! That’s bull!

28:05 > That’s just creepy, man

28:40 > Sheetmusic? She plays an instrument besides piano? Huh

30:06 > Across the street you say?

30:24 > Okay, that was funny xD

31:13 > Nonnyyy, the icoonnn

31:49 > She iss!!

33:22 > STANLEYYYYYYY :DDDDD

33:38 > stanley is sooo judging him rn xD

33:44 > I forgot Stanley is his pfp xD

34:21 > she legit looks about 10 years older than him…

34:45 > Nuuuuuu Naaate :0

37:17 > Simon knows everything, Addy. Also TJ is such a sweetheart

39:31 > Ok, so, we watched the first 2 episodes in class a year ago and I fucking hate this part I get so much secondhand embarrassment so I’m sorry Janae but I’m gonna skip ahead

42:21 > Nooo, c’mon Nate! Don’t do this!

43:14 > oooooooooooh?

43:27 > Wait, so if Jake is in the pool he can’t have posted it, so it must have been Janae? If she had to write that my god poor girl qwq

44:43 > how tf did anyone get into the trunk? did she leave it unlocked? C’mon Bronwyn!

Total note count for episode 1: 96

Episode 2

00:37 > his hair is even more of a mess than usual xD

00:44 > Wait is this a flashback to when she cheated :000

00:49 > re really doesn’t

01:02 > please don’t fuck outside on the grass

01:07 > now THAT, is a view I really do not mind ;))))

01:5? > hair police? yours is literally the most basic hair ever, you have no right to talk

03:34 > shweeties

04:19 > is that a food truck right outside their school????

05:09 > yeowch

05:38 > the idea of Simon running a podcast, exposing ppl is actually a really fun concept xD

06:20 > not the contact name being “Asshole” xDDDD

06:55 > :00000000000000 Daaaaaaaaamn

07:36 > Nuuuu, Keely qwq babyyy

08:05 > i assume the teacher was turned around because that was so obvious addy!

08:20 > Bruh’s got a death note xDD he would be the type tho

08:56 > what was the notebook forrrrrrr Simoooonnn

10:00 > how tf did this random officer know that’s Addy?

11:58 > really? cmon now, thats so shitty xD

12:19 > more like Homiecide xD

13:42 > why tf is this mom reading AboutThat? xD

13:53 > HES THE MAYORS KID? Ooooh he got the moooooneeeeyyyy

15:02 > Addy……. qwq

16:09 > that was faaaaaast, coop xD

18:03 > :000000000000000

18:10 > Nooooooo, Coooooopppp qwq

20:52 > ok thats actuall kinda cute qwq can you imagine lil kid simon?

22:27 > Two late, two phone related detentions… interesting

24:07 > jis house is so prettyyyyy qwq I wanna live there!

24:16 > TINY SIMONNNNN OH MY GOD BABYYYYY QWQWQWQWQWQ

25:16 > Simon’s mom is fiiiiiiine, I see wher he get’s his good looks from xD

15:29 > Janaaaaaeeee qwq

26:26 > Simon in a suuuuiiittttt Lord have mercy!

26:38 > those fucking professionbal, model photographs xDDD

26:53 > How did she know where his room is? It’s a very very nice room tho, if I may

27:12 > wonder what that sign says…. also his bed looks nice! really comfy too :)

27:43 > look at that fucking setup man! daaaaaamn

27:50 > why is there fucking steps at the door??? xD

28:55 > can I just emphasize the fact his room looks so nice??

29:54 > yeeeeep he def got his looks from his mom, his dad is uglyy xD

30:11 > it would not, actually. not at all

31:25 > i dont think thats the best conversation starter, Maeve xD

32:08 > he did not go to hell! >:0

32:50 > A DRUMSET? AND A GUITAR????? HELLO WHERE IS THAT CONTENT?????

33:32 > Bronwyn can you stfuuuuuu you’re only making this worse

33:47 > atleast hes honest xD

35:07 > this house is so pretty qwq i am so jealous qwq

35:44 > “the incredible hair” pffff

37:56 > A, and I cannot stress this enough, WOOGA

38:59 > I’m gonna fucking scream he looks so goooooododdddd my lord i will not survive

41:22 > I am still not over that giant fucking picture of SImon in the background xD

42:46 > Girl the only thng you did was cheat ona  fucking test it’s not the end of the wrld!

46:48 > since when are full names used? wasnt it just initials in the book? now this is just evil, initials multiple ppl can have, but full names? C'mon dude!

47:25 > MAEVE??????? WhAT THE FUCK???

Total note count for episode 2: 53

Episode 3

00:17 > Keelyyyyy babyyy I love her qwq

00:47  > shes such a shweety qwq

00:59 > another PERFECT OUTFIT 10/10 MY GOD

01:04 > I don’t even know what to say at this point

01:38 > he diiiiiiiiiiiiiiiiiiiiid :)

02:14 > no you fucking dont!

02:55 > Addy is entering her girlboss ear and I love that for her

03:33 > bruh please just use a hairbrush xD

05:20 > its goin down!! hands are being thrown!!

06:39 > addy needs a hug qwq

07:42 > :0 escandalo!

09:10 > they kinda look like siblings wait i love it qwq

11:42 > the laptooooppppp :0

14:51 > okay Janae’s outfits are also really nice, i get why they were bffs xD

16:08 > :00000000000 MAEVEEEEEEEEE OH MY GOOOOOOOOOD

17:13 > why do literalyl all the parents in this suck?

17:39 > Addyyy what are you doing? 

17:53 > Addy! No!

19:21 > TJ looks like a kicked puppy qwq

21:14 > you didnt say it but your face sure did

22:26 > and another perfect outfit!

22:29 > he just keeps getting finer, huh?

22:47 > Daaaamn Simoooooon! :0

22:56 > he looks so ethereal, like an angel or god of some sort :0

23:15 > omg Simon is shmol qwq shmol bean

23:33 > the rings, the bracelets, the necklaces, LORD HAVE MERCY PLEASE

24:20 > NOT NATE :00000 NOOOOOO

29:17 > i love that Addy is dressing for herself now qwq

30:26 > Nooo, Coooperrrr qwq

31:18 > i know that was meant to be all angsty and stuff but it just looked so weird xD

33:56 > Awwwww, Janaaeee qwq

36:13 > WHAAAAAAAT THE FUUUUUUUUUUUCK :000 I mean same, but still, I was NOT expecting that

36:53 > :0000000000000000000 my exact face rn

37:39 > oh yes we are bronwyn!

38:19 > DONT DO IT COOPER PLEASE QWQ

40:45 > There he is again, in that amazing outfit!

41:05 > his faaaaaaaaace oh my god cooper you have a death wish or something?

42:36 > out of all the 4 stories, bronwyns is the most boring to me xD

45:21 > “straight cosplay” pffffff

Total note count for episode 3: 39

Episode 4

00:31 > his outfits never miss! they’re always so good qwq

00:41 > I love that he’S smaller than atleast 3 of the 4 others xD

01:47 > STANLEY! :D 

03:20 > Janae with her hair down tho??????

13:33 > Stanley’s just listening in to all the drama xD

22:30 > how about Addy and Janae just get together? I would not complain xD

24:54 > “actual lizard” pffffff

26:13 > IT WAS JANAE???? NOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO QWQ

39:22 > Mf looks like a goddamn cryptid xD

41:32 > oh my god hes PISSED you can see it in his faceeee

44:19 > Maaaaaaaaaeve what are you doing????

44:50 > Its momther!

Total note count for epsiode 4: 12

Episode 5

02:00 > if I was sitting in Bronwyns spot I would not be able to focus at all xD

03:20 > Yes addy!!!! Looking good! rocking the short hair!

06:36 > where tf?

13:43 > wtf Cooper???

18:28 > Bronwyn can you not be an asshole for one episode please?

19:02 > MAEVE WAS WHAT???? TO SIMON??? IM SORRY????

21:29 > Bronwyyyyyyyyyyyn whyyyyyyyy oh my god! 

23:52 > they look like such lesbians and I am living for it

33:11 > and ANOTHER perfect fit from Simon, god damn!

39:52 > Please don’t leave Stan behind qwq

Total note count for episode 5: 10

Episode 6

01:07 > janaeeeeeeee that loooook I love itttt

4:31 > “then one summer he got abs” pfffff

04:52 > Janae gave him the idea?????

16:35 > Members of Simon’s what????

21:33 > Awwwww, wait, that’s so cute qwq I knew Janae couldn’t be straight when she dresses like that xD

22:03 > Their dynamic is just chefs kiss xD

22:26 > You can make a move on my anyday xD

33:10 > :0000000000000 NOW THAT IS NOT SOMETHING I EXPECTED TO SEE BUT I AM VERY MUCH WELCOMING IT

36:14 > why are they fucking burning the epi-pen?

37:16 > thats wierdly sweet qwq

37:29 > I know I’m just repeating myself at this point but Simon really does have the best outfits

37:48 > Ayooo? AYO???

38:37 > What if Janae, Maeve and Simon just get in a poly relationship? Problem solved xD

38:51 > His humourrrrr

40:00 > LESBIAAAAAAAAAAAAANSSSSSSSSSSS

40:25 > AAAAAAAAAAAAAAAAAAAAAAAAAAAAA FUCK YEEEEEEEEEAHHHHHHHHH

Total note count for episode 6: 16

Episode 7

09:08 > The lighting in all of these flashback Simon scenes is just so good qwq

30:32 > i would also 100% be zooming in on that xD

31:43 > that’s boat racism xD

31:47 > again, his humourrrrr top tier

Total note count for episode 7: 4

Episode 8

00:17 > I don’t want it to be over yet qwq I want more Simon qwq

03:06 > that is such a simple signature are you kidding me?

11:29 > I seriously need to calm down xD I can’t keep reacting like this any time SImon is on screen xD

11:41 > THE LIGHTING AND WINDOWS AND FRAMING AND OMG

12:08 > pfff the sheer “what the fuck” on his face xD

15:30 > AAAAAAAAAAAAAAAAAAAAAAH one day I will just die because Simon keeps looking that good!!!!

16:40 > do I even have to say anything anymore? like at all?

17:19 > “the magic words”? are you for real xD

25:39 > so him having a lizard is a reason you like him?

27:48 > lookatem with his fucking headset xD you know he streams and just annihilates little kids on vc xD

28:16 > wait so… Simon… didnt even want to kill himself? so really Jake is the reason this all happened…

41:30 > WHAT THE FUCK IS GOJNG ON?????

42:28 > So Jake… killed… Simon? Jake is the reason he’s dead, Simon didn’t want to kill himself Jake killed him! Holy fuck this is different than the book…

42:52 > God Janae looks TERRIFYING

43:24 > YEEEEEES JANAEEEEEEEEE KILL HIIIMMMMMMMMMM GET REVENGEEEEE

44:11 > I’m not even remotely sad about this. I’m happy, really

44:21 > I still cannot believe that JAKE is the reason… welp, I know what headcanons I’m making next

44:29 > …

44:42 > YES AND HE SHOULD HAVE

45:05 > I AM ACTUALLY CRYING STOP HE LOOKS SO TERRIFIED NO

45:35 > now you will cuz YOURE OTH FUCKING DEAD

50:58 > Now what if Simon actually didn’t die? Like imagine that, Jake’s plan all going to waste!

Total note count for episode 8: 25

Total note count: 255

Welp, there you have it xD I put them all together because posting one post for every episode or a pair of episodes, eventhough I'd have to split episode 1 in half, would just be too many notifications xD

So here you go, I hope you enjoy my thoughts while watching OOUIL. :D

I read pretty much all of these (except the full fics or the poly stuff) but like THEY'RE SO GOOD AND I'M SO DOWN BAD BUT THAT'S OKAY I highly recommend reading them if you're just as much of a sucker for fluff as I am <3 great fucking job, 100% gonna read all the rest on the 2nd list too now

💚❔ Dano!Riddler Masterlist (1)❔💚

(So this is the first masterlist for Dano!Riddler which as all my previous works on him up to 100 links 😂 if you want to see ones I’m posting now, check the second masterlist!)

Headcanons:

Dating Edward Nashton/The Riddler Would Include

Fluff Headcanon

Overexcited Affectionate Edward

Soft Yandere Headcanon

Comfort Cuddles Headcanon

Cats With Edward Nashton

Comforting Headcanon

S/O Working At The Iceberg Lounge

Shy, Complimenting S/O

Crybaby! S/O

Edward Babying His S/O

Texting Headcanon

Cuteness Agression

Clingy After A Trip

Kissing Headcanon

Artist! S/O

Protective Over Livestreams

Night Cuddles

Pet Names For S/O

Violinist! S/O

Affection As The Riddler

Harley Quinn! S/O

Social Media Star S/O

Pregnant! S/O

Cat-Called S/O

Streaming Support

Hugs And Cuddling With S/O

S/O With Glasses

Protective With Upset S/O

Shy Around A Girl He's Just Met

Edward Protecting An Innocent S/O

Edward With A Timid/Quiet S/O

Friends On Twitch

Reacting To His S/O Having A Panic Attack

Gamer Girl/Nerd Follower

Eddie And Short S/O

Eddie And Tall S/O

Sleeping With Edward (SFW)

Obsessed With Edward Nashton

Arkham Attraction

Chaotic Criminal S/O

Vigilante/Super! S/O

Insecure S/O

Imagines:

Three Riddles

Love Me More

Used To It

Hair Play

Stranger

All In Twenty Minutes

The Couple

Tell Me You Love Me

My Wonder

Fighting For You

Is That My Shirt?

'Heroine'

Fake Blood

Touch Starved

Soulmates

You're Safe

Love You Already

Solving A Riddle

Attention Seeker

Marrying The Riddler

The Diner

My Riddler

Beginning But No End

Forever

Can't Find My Glasses

He's The Riddler

Orphan Angel

My Clever Girl

Flustered

No More Nightmares

Nightmares Again

Slow Dance

Happier Birthday

Behind Bars

Vulnerability

'I love u <;3'

Insecure Eddie

Angelic

My Goddess Is Live

Ave Maria

High Treason

Cuddle Sessions

Comfort My Clever Girl

Sick Day Comforting Nashton

Full Fics:

Acid Reign - TEASER

Hope - PREVIEW

Hope - DRIVE

Hope - YOU CAME

Hope - HOPELESS

Hope - THE BIG PICTURE

Hope - TARGETED

Poly with Battinson:

Battinson & Riddler Headcanons:

Period comfort (separate)

Battinson & Riddler Imagines:

Overtime (Part One of Batman x Riddler x reader fic)

Poly with Keoghan!Joker:

Joker & Riddler Headcanons:

Check the second masterlist!!

Joker & Riddler Imagines: Break Out

Hello yes I posted an update :) I'll do this every time, cuz you don't get notified when I update a post and I wanna make sure you all get notified!!

Dating Simon headcanons

If you know me, you know I literally made this account because Tumblr was the only soure of Simon screencaps etc I had. And, since I am writing what I believe to be the first ever Simon x reader fic on the entire internet over on AO3, I thought I’d feed you all some more. So, here’s some headcanons of what I think it’d be like to date Simon. Might also include NSFW if I feel like it/if anything comes to mind, but it will be marked with 🍋(real original, I know) so you can skip it if you want to. It is also currently 2 hours past when I’m supposed to go to bed and I haven’t gotten proper, 8 hours of sleep in like a month so yeah, apologies if there’s any grammar mistakes or anything similar.

They’re all kept gender neutral, and reader is referred to as ’you’.

Emjoy.

TELL HIM YOU LOVE HIM AND HE WILL MELT

Ok, sorry, I’ll calm down

But seriously, we know this kid hasn’t really gotten that much love or compassion from others, and probably was never even in a real relationship before you, so whenever you express that you genuinely like him and want to be with him, he kind of schort-circuits

He’s also kind of worried you’re only with him to get info on others, and once you’ve got enough you’ll leave him, and that it’s all a cruel joke

But, again, if you reassure him that no, you’re not just here for info and you do infact love him, he’ll slowly learn to not listen to the voice in his head, it will take a while tho, so get ready

Of course, since it’s Simon, if anyone ever messes with you, in any way shape or form, be that at school, online, strangers in public, whatever, he will have them on display on AboutThat the next morning, or even within a couple of hours, front and center. He doesn’t really care who it is, but if they mess with you, they mess with him too

🍋 Now we all know Simon likes to feel all high and mighty, untouchable, right? So, might I suggest, that Simon would probably enjoy power play? Of course he’s always the one with power, and I feel he’d get a reeeeeeal kick out of getting to use you however we wants (with your consent of course, he might be an ass who kinda ruins peoples lives but he’s not a monster). If you’re into it too then even better! Though he’d never push you too far, he doesn’t want to hurt and maybe even lose you! Call him something like Sir, Mister, Master or anything of the like and wheeeeeew you’ll be in for a ride. Most of the time literally xD

Simon is definitely terrified of losing you, I mean you’re one of, if not the, first people to really care for him. He’s always worried that he’ll say or do something wrong and that you’ll leave him. :( please do reassure him you won’t leave, it will probably end up with him crying, though.

At school, of course, he’s all cocky and confident, but I feel with you, in private, be that at yours or his place, he’d stop being so braggy, and actually be quite touchy and affectionate and quiet. I can imagine you two just sitting on whoever’s house you’re currently in’s bed, both sort of doing your own thing, but still leaning on another, maybe occasionally saying a few words, but mostly keeping quiet. Sometimes the Tv will be on in the background, playing whatever channel was last on, sometimes it’ll just be music, or maybe even nothing, only the sounds of both of you clicking away at laptops, phones, the sound of pages in a book turning, whatever.

I think we can all agree that Simon is probably pretty touch-starved, I mean lookatem! At school he’d probably not be that touchy, maybe just holding your hand or his arm around your waist, just small things people easily miss. He’d probably not be the biggest fan of PDA, but also probably would’t hate it. Sure he’s give you a quick kiss or two, but you wouldn’t get into full on makeout sessions in the middle of school. He hates when others do it, so he also won’t.

In private, however, it’s as if he’s superglued to you, always touching you in some way. Leaning on you when you’re both working, holding you when you watch Tv together, you sitting on his lap when he’s at his desk, whatever. He’s always hesitant to let go because his brain tells him that if he lets go, he’ll never get to hold you again, that you’ll disappear.

Maybe, just maybe, you’d even be enough for him to scrap his plan, to not actually kill himself. I doubt he just one random day decided to do it, he must have started planning ahead years before. And it will take a while for him to decide that no, he doesn’t want to do it anymore, because he has you. I feel the day it’s all officially cancelled, he’d probably sit down on his bed or desk and just, take it all in for a bit. Never had he felt this safe and happy with someone before, so much so that he doesn’t want to kill himself anymore. He definitely cries.

I feel you’d eventually find out. Maybe you do by accident, maybe he tells you, doesn’t really matter. Either way, a lot of crying happens. You crying because he wanted to kill himself, then because you are the reason he didn’t and then him crying because of all the emotions and how new this all is for him.

NEW

So we all probably know the song 'Teenage Dirtbag' right? Well, I just heard it on tiktok, the end part where she also sings to be precise, and I dunno why but I just thought of Simon and his S/O. Like he never thought they'd ever even acknowledge him, and when they do he's just like "Wot". I dunno, my brain just does stuff sometimes.

In conclusion: I fucking love Simon, I want him to be happy, healthy and loved and I will gladly give him that love. <33

If anything else pops into mind, I will add it, I’ll mark it too so you’ll see what’s new!

I saw this on my fyp on tiktok

and for some reason my brain was like "That looks like Simon" and now I can't stop imagining that this is how Simon acts whenever he gets drunk xD Janae is 100% the one filming this xD

I think it's the hair that's making me think of Simon xD

Alsoooo if you have any ideas for Simon headcanons please do send them my way! I'll try my best to write up a lil something for them!! I can't promise I'll do all of them, since there's certain topics I really know nothing about, so if yours doesn't get picked I'm so so sorry qwq

Dating Simon headcanons

If you know me, you know I literally made this account because Tumblr was the only soure of Simon screencaps etc I had. And, since I am writing what I believe to be the first ever Simon x reader fic on the entire internet over on AO3, I thought I’d feed you all some more. So, here’s some headcanons of what I think it’d be like to date Simon. Might also include NSFW if I feel like it/if anything comes to mind, but it will be marked with 🍋(real original, I know) so you can skip it if you want to. It is also currently 2 hours past when I’m supposed to go to bed and I haven’t gotten proper, 8 hours of sleep in like a month so yeah, apologies if there’s any grammar mistakes or anything similar.

They’re all kept gender neutral, and reader is referred to as ’you’.

Emjoy.

TELL HIM YOU LOVE HIM AND HE WILL MELT

Ok, sorry, I’ll calm down

But seriously, we know this kid hasn’t really gotten that much love or compassion from others, and probably was never even in a real relationship before you, so whenever you express that you genuinely like him and want to be with him, he kind of schort-circuits

He’s also kind of worried you’re only with him to get info on others, and once you’ve got enough you’ll leave him, and that it’s all a cruel joke

But, again, if you reassure him that no, you’re not just here for info and you do infact love him, he’ll slowly learn to not listen to the voice in his head, it will take a while tho, so get ready

Of course, since it’s Simon, if anyone ever messes with you, in any way shape or form, be that at school, online, strangers in public, whatever, he will have them on display on AboutThat the next morning, or even within a couple of hours, front and center. He doesn’t really care who it is, but if they mess with you, they mess with him too

🍋 Now we all know Simon likes to feel all high and mighty, untouchable, right? So, might I suggest, that Simon would probably enjoy power play? Of course he’s always the one with power, and I feel he’d get a reeeeeeal kick out of getting to use you however we wants (with your consent of course, he might be an ass who kinda ruins peoples lives but he’s not a monster). If you’re into it too then even better! Though he’d never push you too far, he doesn’t want to hurt and maybe even lose you! Call him something like Sir, Mister, Master or anything of the like and wheeeeeew you’ll be in for a ride. Most of the time literally xD

Simon is definitely terrified of losing you, I mean you’re one of, if not the, first people to really care for him. He’s always worried that he’ll say or do something wrong and that you’ll leave him. :( please do reassure him you won’t leave, it will probably end up with him crying, though.

At school, of course, he’s all cocky and confident, but I feel with you, in private, be that at yours or his place, he’d stop being so braggy, and actually be quite touchy and affectionate and quiet. I can imagine you two just sitting on whoever’s house you’re currently in’s bed, both sort of doing your own thing, but still leaning on another, maybe occasionally saying a few words, but mostly keeping quiet. Sometimes the Tv will be on in the background, playing whatever channel was last on, sometimes it’ll just be music, or maybe even nothing, only the sounds of both of you clicking away at laptops, phones, the sound of pages in a book turning, whatever.

I think we can all agree that Simon is probably pretty touch-starved, I mean lookatem! At school he’d probably not be that touchy, maybe just holding your hand or his arm around your waist, just small things people easily miss. He’d probably not be the biggest fan of PDA, but also probably would’t hate it. Sure he’s give you a quick kiss or two, but you wouldn’t get into full on makeout sessions in the middle of school. He hates when others do it, so he also won’t.

In private, however, it’s as if he’s superglued to you, always touching you in some way. Leaning on you when you’re both working, holding you when you watch Tv together, you sitting on his lap when he’s at his desk, whatever. He’s always hesitant to let go because his brain tells him that if he lets go, he’ll never get to hold you again, that you’ll disappear.

Maybe, just maybe, you’d even be enough for him to scrap his plan, to not actually kill himself. I doubt he just one random day decided to do it, he must have started planning ahead years before. And it will take a while for him to decide that no, he doesn’t want to do it anymore, because he has you. I feel the day it’s all officially cancelled, he’d probably sit down on his bed or desk and just, take it all in for a bit. Never had he felt this safe and happy with someone before, so much so that he doesn’t want to kill himself anymore. He definitely cries.

I feel you’d eventually find out. Maybe you do by accident, maybe he tells you, doesn’t really matter. Either way, a lot of crying happens. You crying because he wanted to kill himself, then because you are the reason he didn’t and then him crying because of all the emotions and how new this all is for him.

In conclusion: I fucking love Simon, I want him to be happy, healthy and loved and I will gladly give him that love. <33

If anything else pops into mind, I will add it, I’ll mark it too so you’ll see what’s new!