#romantic madwise

[everythingismadeofclouds]

polyparty (+suzie) headcanons

[pacibyers]

[kaliprasad]

Okay THANK YOU I shall spam you one by one now, but please don't feel pressured to answer all of them or answer quickly or in any order, it's all just fun 🙏🏼 your headcanons just make me really happy ajajaha

Next one 💛 Will/Transmasc!Max

So, this is the only way I can see romantic Madwise working. As a transmasc genderfucky individual, I see a lot of myself in Max, so the transmasc headcanons were inevitable and is something I've been writing about/thinking about long before I started shipping this specific iteration of them (before I get comments/asks saying I just made Max transmasc so I could ship him with Will). All other iterations of Madwise are just platonic to me personally. This post will also feature disabled!Max with damaged leg tissue.

Madwise (Will/Max) Headcanons

Max struggles a lot with his appearance, constantly dressing himself in the baggiest clothes. Will ends up loaning him a lot of his shirts because his shirts and sweaters are always bigger (Buff Byers supremacy).

Will is the first person Max comes out to, when they're in college in the 90s and Max is visiting. Will has long since been apart of local queer scenes in his area, maybe even becoming a drag performer in his spare time (I think he would enjoy drag! Sue me!), and has learned a lot about the trans experience of the time from the people he's met in those spaces. So he recognizes a lot of the struggles Max went through and accepts him almost immediately.

Max isn't able to medically transition until the early 2000s, because medical avenues for transition weren't very accessible. They were available, but not the most accessible. Will is the one that helps take him to his therapy appointments that eventually get him a testosterone prescription.

They'd definitely be a slowburn romance. Not because I don't think Will could be attracted to Max pre-transition, but because I think he would struggle to recognize his feelings shifting from platonic to romantic because Max has been his friend for years. And I think Max would just inherently believe he couldn't be attractive to Will because he's trans.

When Will eventually does realize he is attracted to Max, it's at a local Pride Parade they decide to attend together. Max goes shirtless with pasties over his chest, and Will promptly short circuits. (Max isn't much better seeing Will in the shortest shorts known to man).

They end up getting a bit tipsy at at a local queer bar after the parade and going home together, which turns into their first hookup, that then snowballs into future hookups with complicated feelings growing on both sides.

Will tries to move on and not think about it, dates other guys in an attempt to put Max out of his mind. Meanwhile, Max is seething. Because, here he is, putting in the elbow grease and pining after Will, only to see him hanging on some other dude. He gets really in his head about it being because he's trans (it's absolutely not) which causes some strain in their relationship for a while, even if they continue to hookup during this time (angry sex ftw).

Eventually, it's Will entering a really shitty relationship with a guy, his first really bad relationship. Max is there to support him through the entire thing, but is biting his tongue the entire time KNOWING he could treat Will better than that. When Will and this dude break it off for the umpteenth time and he's crying in front of Max about it one night, Max finally breaks and kisses him then and there. It's never a direct conversation after that. Will stops seeing that guy, starts staying at Max's full-time and they just begin dating.

Will loves watching Max skateboard, which is still a passion of his. After years of physical therapy, his legs are strong enough to withstand skating again. Will sometimes goes to the skateparks with him on his rollerskates, but he can't do any tricks (or refuses to, because the last time he tried with Max's encouragement, he absolutely ate shit)

In the same vain, Max loves watching Will paint. He'll make himself a cup of coffee early in the morning and peak into Will's art space to see him laser focused on the canvas. He'll stand there staring for so long, Will eventually notices. It always earns a smile.

They're both horror movie buffs, but they like different genres of horror so they're always arguing over who's 'right'. They both love Ghostface, though (In modern AUs, they both LOVE the Flanagan shows and movies)

They take Halloween VERY seriously. They run that shit like the Navy. They decorate their entire house to the nines with fake cobwebs and gravestones and fog machines. Will is the one sitting outside handing out candy while Max is the one hiding out to scare the (older) kids jumping out from the bushes.

They also both dress up in matching costumes every year for Halloween, but never the cute kinds of couples matching Halloween costumes. It's always either the most elaborate badass costumes you've ever seen, or, like... Bill and Ted. They wear these on Halloween Eve to go to local queer bars (they do this often even not on Halloween but it's become a holiday tradition).

To build on drag performer Will more, Max would be at every performance and would always brag about dating him to anyone in earshot. "That's my boyfriend/girlfriend".

Okay this is getting long I'm stopping myself, but I'm more than happy to dump more about them if someone sends me another prompt! Tagging @stranger-things-yapper because we talked about this recently!

In response to ST Ship Headcanon Ask Game

[stranger-things-yapper]

20 or 35 as madwise

35 - A kiss against a wall, for Madwise!

This wasn't the first time Max and Will grabbed something from a store and left without paying. It was, however, the first time someone chased them to get them to pay. And that was simply not going to happen, you know?

They did target a bigger store, to be fair. They had never tried to steal something from a store that had more than one employee manning it. But they were running out of small places to go without raising suspicion, so they had to try expanding their reach. This department store had shitty cameras, but the manager saw them taking some chocolate bars (unfortunate timing on Will's part for making Max laugh instead of focusing on the task at hand), so they bolted out of there. The manager kept chasing them despite the fact that they had left the store, so Max grabbed Will's hand and dragged him to keep running.

They managed to get a good distance from what was probably the best paid manager in the country - if he was this willling to run so far after them - and rounded a corner. If they could hide in a alley or something, they could probably lose him now. Will was running in front of Max now (to her annoyance, the ridiculous advantage of being taller at play once again), never letting go of her hand. He quickly found a slim corridor between two buildings and pulled her into it. He pressed his back to the wall next to the corner, and pulled her flush to his chest, hands still linked. Will's face was turned, trying to peak behind the corner; Max leaned to the side in the same direction, checking if they could see the manager without him seeing them as well.

"Do you think he gave up?" Will asked, breathless. Max could feel the rise and fall of his chest under her other hand.

"I don't know," Max replied, equally breathless, "I'm kinda rooting for him now." Will's gaze met hers, wearing an incredulous furrow in his eyebrows. "If he keeps running like that, he might classify for the Regionals!" She joked, causing her and Will to laugh. He screwed his eyes shut with his laughter, leaning his head back against the wall while bringing an arm around Max's shoulders and the other hand to the back of her head. Just to hold her even closer. Max kept laughing over the fabric of his shirt.

"What, it would be a real underdog story! They might make it into a movie one day!" She pushed her head off his chest and leaned it back to grin at him while she continued. He was so much taller than her now; her eyes were leveled with his Adam's apple. She wanted his laugh to keep going forever. "Track Star Manager, in a theatre near you!"

"Shut up!" Will said between laughs, to which Max giggled even more. He pushed his head away from the wall to face her, a wide smile on his face. The movement made their faces be closer - too close for friends. Max was suddenly aware of how much body contact there was between them, now: torsos together, her hands on his chest, one arm around her shoulders, the other hand still in the back of her head. Will was looking into her eyes, softer and warmer than the bright happiness of before. Max could see every detail of the hazel iris from this close. Their laughter slowly died. Max's heart started to race.

Will's eyes dropped to her lips, and Max involuntarily let out a shaky breath. He was still smiling when he ducked down to kiss her.

She only knew she had expectations for how he'd kiss her when their lips touched. It was soft, and slow, and she realized she knew it would be like this; she had known, somehow. There was no rush, no desperation, no tears and no anger - in fact, she could still feel him smiling against her. And the thought of Will being like this with her made something flutter in her stomach. It was what made her push onto her toes to press deeper into the kiss. He felt so content against her that she wanted to soak herself in the feeling. In response, Will held her even closer, the arm around her shoulders dropping to pull her around the waist, the hand on her head positioning itself under her hair, meeting the skin of her neck, tangling between her curls. Max fisted at his shirt, yanking him down with her when she lowered her heels back to the ground, refusing to break them apart.

When they finally stopped to catch their breath, Will moved to kiss her cheek, and Max couldn't help the smile breaching her face. She thought she was giving him happiness; turns out he was multiplying hers.

Here's the post for prompts, if you want me to write some more kisses!

[milktoast-mileven]

Will and Max were such a waste of potential.

[willelmax-and-other-ships]

Byler, Madwise, Byclair and Will x Suzie are my favourite Will ships.

[pacibyers]

I LOVE MADWISE

[everythingismadeofclouds]

max and will flirting as a joke until max comes out (🏳️‍⚧️) and it suddenly doesnt feel like a joke anymore