My Oswalda cobblepot and Rupert Thorne headcanons
I'm just gonna start off by saying I believe they're exs, both a headcanon and a theory
The mother of his son was killed, not by Oswalda, but another business enemy.
She was a passing fling that just so happened to get pregnant
She was the one who provided the protection and purposefully tampered with it in hopes of baby trapping Rupert and getting set for life (didn't work out in her favor).
Rupert found out quickly and provided no security for her after his son was born, leading to her dying incredibly quickly after.
He started showing interest (not romantic yet) in Oswalda once he noticed her rise in the illegal business.
He figured the best way to shoot her down was by breaking her heart (not knowing her true personality).
He thought that some of her public persona was genuinely who she was, boy would he be proven wrong.
He accidentally got invested in the relationship and was absolutely smitten with her.
His most fond memories of the relationship is when he would hear her singing or humming while doing her makeup or in the shower, her voice haunts him.
His pet name for her was songbird, he still uses it while talking about her in private.
He was the one who ended the relationship, he didn't like how she would put work above all else and not even seem like she was interested sometimes.
He is such a yearner but hides it incredibly well.
He'd never admit that his plan backfired and left him with the broken heart instead.
The only reason he goes to her parties is to hear her singing and he will leave quickly when he realizes she's done performing.
He knows if he doesn't leave that he'll start thinking and do something or say something he'll regret.
He wants to visit her in prison/Arkham asylum (where ever she actually is) so bad.
He would have gone to her last party earlier if he knew it was her last, but he was late trying to sort out the destruction she caused.
He desperately wanted to bribe the judge and jury to get her acquitted but stopped himself.
He also wants to bail her out (she doesn't have a bail, but he can make a price) and bring her back home but he knows it won't end well.
He acts like he doesn't care about her, saying stuff like "I almost forgot about her" and "she's still around?" When someone mentions about her but in reality she keeps him awake at night.
He will also give her rude, kinda school yard bully esc, nicknames when talking about her or crack a joke at her penguin nickname.
Despite being emotional, he can still be as ruthless as her, he just doesn't like and actually expresses remorse when his private life and work overlap causes the ruthlessness.
Nobody knows who her husband was, what happened to him or anything about their relationship. All people know is that she wore a ring for a brief time and had three sons.
She was immediately able to see what Rupert was trying to do when he asked her out but decided to play along.
She had her own plan of becoming a black widow, unsurprisingly.
She didn't let him immediately see her true self until she knew he could be trusted a little bit with her style of pest control.
After almost a year into the relationship did she allow him to see the full extent of merciless style, by letting him watch her kill her third son.
She genuinely doesn't have maternal instincts and it doesn't help that her sons looked so much like their dad.
She doesn't care about relationships or family but there is one person in her heart and it is Iggy, treats him more like a son than her real sons.
Was not invested in her relationship with Rupert at all but played along because having a little puppy follow her around was nice (and so was knowing what your business enemy was doing all the time).
Of course her acting mask fell off every now and then, letting him see she was uninterested but he assumed it was just work making her act like that.
Despite not being invested, she didn't take the break up well at all. She took it as an insult to her persona and was more angry than sad.
After regaining herself, she started noticing little things that hinted that he missed her and got petty.
She'll only sing break up and love songs at her performances to mock him and hurt him.
She's more subtle with her hatred like that.
She'll avoid his direction and keep her back to him while performing.
She won't glance at him while being formal at her parties, making it to where he has to approach her to talk.
She'll slip any synonym to the word tiny she can into conversations with him, take a wild guess on why.
Will be respectful when talking about him to others though, gotta keep a good image.
She found out that he wanted to have a kid with her before she showed him her son's death, after the relationship. It makes her giggle to think about how he loved her so much that he wanted a family.
I also want to say that their relationship was like 2 and a half years, long enough for him to miss her so much, short enough that you don't wonder what took him so long to end it.
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