DON'T PLAY*

“sure it is,” he insists with a shrug, smiling down at her. shego may not be the person flynn was meant to end up with - but that didn’t mean he wasn’t certain she was still going to be a part of his story. “you fit right in mine. in the north wing of my castle i’m somehow going to own. maybe through being the greatest actor ever to live - maybe we’ll just steal it. either way, you’re gonna be there.”

she couldn’t help but laugh a little bit. “you’re going to give me a place to live at your castle? the one where most of your other friends will probably be living at? i dunno if i can handle that many roommates. one is already a lot.” she was mostly joking. “you’re a surprisingly wonderful actor, okay? and as long as your castle is your own and not blondies i’m proud of you.”

send me a 🌟 and I’ll give you a headcanon about our character’s relationship

gogo was very much a rebound a first. they hang out at the same places sometimes, they both like to move fast,and they are both ridiculously gorgeous so it doesn’t take much to figure out how they ended up getting together. shego liked that she could probably kick anyone’s ass if provoked and how she was too smart for the people in the bar. and when they were together it was pretty physical. it was brief, but it was a ride.

shego does have a little bit of regret for everything. not because she didn’t have any sort of feelings for gogo but because she actually liked gogo and knows she deserved better than what shego put her through. because she was pretty aware she was just trying to get over flynn, but she also tried really hard to make things work. it just....didn’t.

now shego is really trying to be friends. she flirts like hell with gogo still, but she can’t help it! she wants to see gogo with someone good for her and she will beat a man or woman up if they try shit with her. she looks out for her in her own way and gogo never seemed mad about it so she figured she would just keep doing what she’s doing until gogo says something.

send me a 🌟 and I’ll give you a headcanon about our character’s relationship

as much as shego doesn’t like to admit it, drakken really came through to her when she needed him the most. sure, she started working for him when she was still a teenager, stealing things for him and his work,  but she didn’t move in with him until she was an adult and ran away like a responsible rebel. he was never creepy, just a sad man who clearly had no friends. shego didn’t really have any either so it worked in its own way. shego is actually fine with her current arrangement because he never invades her privacy and gives her more respect than her brothers and parents ever did.

he steals her headphones a lot and uses her apple music account all the time. shego only knows of this because the weirdest songs will start being suggested and she sure as hell knows what she likes. she hasn’t called him out on it yet because she knows it won’t stop him. he may be afraid of her, but he knows she won’t hurt him too bad.

now that shego has her new powers, drakken is constantly trying to see what he can do to make her blast random objects. he says it is for science but shego doesn’t like being treated like a lab rat so 9/10 times she is blasting something above his head. he just starts standing where he wants her to hit now. 

as shego let go of his chin, he quickly shook his head. “no you aren’t. not in this story,” flynn argued. as she stood he remained down on his knees and simply leaned back some to look up at her. “this is our story, gogos. we’re the protagonists which means we get our version of a happily ever after.” finally slowly standing up he moves to stand by her side, wrapping an arm around her waist and leaning against her a bit in his semi drunken state. “which means lots of money. and sex. and freedom.”

shego stiffened at his embrace. he might be comfy but she was not drunk enough for this. talking like that made her think of the old times; laying in bed without a care in the world because she didn’t feel so alone with him by her side. she couldn’t let that slip through her exterior more than it already had been. this really was a mistake. “all that huh?” she said, slighltly bitter. “i don’t think this is the story you really want,” she continued, quieter this time. “i don’t think i really fit into your happily ever after.” or anyone’s. 

shego sighed, looking down at flynn with a gleam in her eyes. “now flynn,” she began, hand slipping from his as she stepped away to crouch down in front of him. her hand cupped his chin and she smirked. “we both know i’m the bad guy.” she almost added the duh but didn’t want to come off too corny. “and the bad guy normally ends up in jail or dead and not with their so-called happily ever after.” she moved away from him, getting back up. “this is the last time i try to help you out.”

send me a 🌟 and I’ll give you a headcanon about our character’s relationship.  

flynn was her first real relationship. she has flirted, hooked-up, and teased plenty others in the past, but flynn was the first serious relationship she ever had. she didn’t have to act tough around him all the time, and she didn’t have to pretend she was okay when she wasn’t. sure, they were criminals to an extent, but they were very bonnie and clyde during their run.

as much as they worked together there were a few issues. shego lived with drakken, which was weird and still is, and flynn clearly wanted more out of his “friendship” with rapunzel. eventually these issues were too loud to ignore and all it took was an ultimatum to split them up. shego has yet to really move on but she isn’t sure why. she had had other relationships since, mostly brief, but for some reason she is hung up on him enough for it to bug her.  it’s probably because he was the first and last person she was vulnerable with.

she tried to just kick him out of her life, but that hasn’t really worked. as much as she never wants to admit it, she likes being his friend. of course their version of friends or even acquaintances is not standard. but it works for them right now.

she used to steal stuff for him. little trinkets and gifts that made her think of him. sometimes she still does out of habit. sometimes she keeps them, sometimes she drops them off at the orphanage if it’s kid-friendly. but she hasn’t told a soul about it.

“i don’t have any. letting flynn get close to me. it was the biggest mistake to let anyone close enough in my heart to hurt it. i won’t ever be foolish like that again.” @theflynnriders

“...............” Yeah and? Only when I’m lonely.Then I remember I’m hot and can fuck just about anyone. @mcgalomaniac

“no,  but isn’t that the fun with me? that i’m a forever mystery?” she was joking for the most part, but at the same time she wasn’t. she knew she wasn’t fair or open or outstanding to gogo; at least she wasn’t when they were together. but she tried to be better;she tried to be more open, see her sometimes, flirt and junk. but she supposed even then she wasn’t really being super open. and she didn’t owe it to her necessarily but shego wanted to be her friend so she kind of did. “okay, okay. what do you really wanna know, gogo? i will be an open book to you.” @tomagogo

Flynn: Wait.. power? You got one too?

Flynn: Why do I feel like I should be scared?

Shego: oh honey, you should ALWAYS be scared.

Flynn: You want me to come to you or do you wanna come to me?

Flynn: Pascal's not home. And I already know Drakken probably hasn't left your place lately.

Shego: Do you think I honestly care if Drakken is home? He is too focused on his shit and I'm focused on mine. But I'll go to you.

Flynn: You miss me, admit it.

Shego: what if i DO miss you?

Flynn: You can't take back that match. Block me all you want but this lasts forever.

Flynn: [screenshot of the "you matched!" screen with the two of them]

Flynn: 😜

Shego: oh that?

Shego: my hand slipped.

Flynn: Wait. Why won't it let me message you?

Flynn: Googoooos. Did you really block me?