Yandere Toons x Reader: An Anthology of Headcanons and Scenarios

The Warden (Platonic & Romantic Headcanons) (Superjail!)

TW: Mentions of Violence & Death, Incarceration, Implied Child Abuse (not by the Warden), Emotional Manipulation, Toxic Mindsets.

A.N. - My first piece of 2022. Time for a siesta, and Happy New Year!

Platonic:

The lens through which the Warden views relationships is tainted by an isolated and brutal childhood, with the unruly treatment by his father and his prison cell for a bedroom curbing his emotional growth. His only semi-positive connections to living beings are his employees Jared and Alice, so he aspires to rush his friend into a deep and lasting relationship before it develops naturally. The Warden does his best to plough through the early awkwardness via disregarding boundaries and struggles to reap the intimacy that he has fantasized about for years.

As the world he was born into provided little kindness and exterminated innocence like a pest, the world he created in Superjail has a similar absence of morality. The Warden believes that he is a decent man and claims to hope for the redemption of his prisoners, yet he uses his aptitude for causing others pain to resolve any issues in his friend's life. If someone is giving them trouble, he offers to have the offender imprisoned in solitary confinement on bogus charges.

When his friend enters the same room as him, the Warden ignores everyone else in favour of bombarding them with casual observations about the misery of the prisoners and complaints about their alleged neglect of him. He refuses to understand the concept of them having other responsibilities and ideas for how to spend their day, and he responds to anyone else desiring their company by calling the person clingy and trying to shame them into dropping the subject. His idea of quality time revolves around supplying his friend with snacks and drinks while the two of them watch the grotesque execution of inmates.

Romantic:

The Warden overflows with excitement whenever he has the opportunity to interact with his partner, and he sees no need to bridle or disguise it. He fabricates the silliest and most illogical reasons why he needs to interact with them at any given time, ordering either Jared or Jailbot to send them to his office when the frequent urge to seek their attention strikes him. These sessions typically involve conversations about a future rendezvous that his partner is not aware of and what he phrases as a relationship destined to last forever.

Despite his lack of a verbal and behavioural filter, the Warden enjoys a rich inner life that is not immune to insecurity. He falls prey to self-doubt when it comes to inviting his partner to social events, and he is overjoyed by their simplest expressions of approval. To avoid contemplating the possibility that his affection is unrequited, the Warden aims to smother them with so many compliments and so much of his undivided attention that, in his mind, they have no justification for rejecting him.

If the Warden, during one of his strolls through the prison, even thinks that he overhears someone mentioning his partner, he rushes to join the conversation and hijacks it with random facts and personal thoughts about them. No one is more knowledgeable about their interests and preferences than himself in his opinion, and anyone who tries to correct him or expresses doubt in his supposed expertise is subjected to angry rants about just how wrong they are. If his partner disagrees, he still treats the event like an inside joke and never admits that he may have invented a truth to seem close to them.