Yandere Toons x Reader: An Anthology of Headcanons and Scenarios

Oswald Cobblepot (Platonic & Romantic Headcanons) (Gotham)

Warnings: Mentions of Gore, Violence, Blood, Stalking, Alcohol Use, Reckless Use of Firearms, Mentions of Torture, Death, Undeath, Desecration of Corpses, Mention of Kidnapping, Incarceration, Criminal Enterprise, Emotional Manipulation, Toxic Mindsets.

Platonic:

From his days of spying and backstabbing as a human footstool for Fish Mooney, Oswald has understood that most relationships are transactional and devoid of real intimacy. Hence, he becomes so readily attached when someone goes out of their way to make his time on this earth a little easier.

In this person, whom he now wishes to have as a lifelong friend, Oswald sees a shining exception to human ugliness, for whose sake he is willing to break laws, spend vast sums of money, and take lives to keep with him. The late Gertrud Kapelput taught him that one must give everything to those dearest to one's heart, a lesson Oswald will honour for the rest of his life.

In addition to assassinating people on his friend's behalf, this devotion translates to buying out entire inventories of jewellery and clothes for them. He offers free drinks at his nightclub, guarantees protection if they operate a business, and provides super-secret special access to all his mother's recipes.

Being sentenced to Arkham or Blackgate is no matter when Mayor Cobblepot is eager to finagle the early release of an old friend. He will blackmail, intimidate, and coerce all the appropriate offices until the person he wants is back with him. Oswald becomes exceedingly irritable and anxious if separated from his friend for too long.

He relies on them to lend him an ear whenever he needs to castrate a rival verbally. Although he is not the most cooperative, Oswald is sensitive to any advice from his friend, a sensitivity that doubles if they tell him he is a good man.

As soon as they are more than a few hours late for a meeting and have not contacted him with an airtight explanation, Oswald is howling at his goons to find them and phoning the GCPD to babble about filing a missing persons report. He refuses to sleep or stop pursuing their alleged killer after his worried heart tells him they lie dead in an alley.

Oswald is drowning in grief and hysteria, attacking anyone who delivers bad news about the search when his friend returns to him alive. He collapses into their arms and rejoices that he can delay learning how it would feel to live without them a bit longer, at which point he begs them to clear their schedule in favour of accompanying him through his day.

If anyone dares make a laughingstock of this relationship and, by extension, him, Oswald paces up and down his home while guzzling wine and ranting about how he will roast these people's entrails like chestnuts over an open fire.

Practising emotional honesty for something other than anger takes every courage Oswald can summon. It is safer for him to live out his days half-satisfied and fantasizing than to put his hopes to the test and risk terrifying rejection, so while he is weighing the pros and cons of coming clean, Oswald awaits a sign that the attachment is reciprocal.

In his ideal world, he lives in his father's mansion and drinks tea with his mother and friend while everyone talks about how he proved the critics wrong and became a great man despite everything. This dream will never come true for various reasons that keep Oswald awake at night, so he persuades his friend to take one of the guest bedrooms and dispatches those who might threaten his monopoly on their attention.

He does much to sweeten the deal, which, when broken down to its most basic elements, is a request for his friend to devote themselves to him, as Gertrud did and as he says he did for them. A gourmet breakfast and dinner from Olga every day are a given, but the only item on which Oswald will not make concessions is permission to leave Gotham.