Yandere Toons x Reader: An Anthology of Headcanons and Scenarios

Jack Skellington (Platonic & Romantic Headcanons)

TW: Toxic Mindsets.

A.N. - No better way to celebrate the holiday.

Platonic:

Jack commands the respect of Halloween Town and almost all of its residents, for his word is the supreme authority in that holiday world. While the ever-packed schedule that comes with such a demanding title prevents him from seeking his friend out, he wishes for them to be involved in his projects and asks the locals to retrieve them so he can hear their opinion on the festivities.

Monotony is a burden that weighs heavily on Jack, and he looks to his friend to add a positive spice to his daily existence. Despite not initiating most of the interactions, Jack tends to extend visits and conversations with them for longer than is necessary. He is happy to fill their silence with his raving about his ideas for a Halloween that surpasses the previous year.

Exploiting insecurities and playing with emotions is not the way of the Pumpkin King. He abhors many expressions of traditional rudeness and limits his questionable behaviour to the intimidation of anyone who treats his friend with less respect than he is treated, working instead to be a figure of admiration in the mind of his friend. Jack is principally a gracious leader, so the worst of his wrath is reserved for when his friend is threatened or placed in a dangerous situation.

Romantic:

The Pumpkin King is worshipped as a folk hero by the citizens of Halloween Town, thereby restricting his partner's ability to have meaningful discussions about any concerns or complaints they may entertain in regards to the relationship. The recurring argument is that their position of eternal companionship with Jack is a highly enviable one and should be viewed as a priceless stroke of luck.

Jack's understanding of the relationship gravitates towards the myopic, which results in him believing that there are no pressing conflicts and any doubt expressed by his partner is of minimal concern. It does not require a surplus of bonding experiences before Jack is convinced that the relationship is everlasting and incapable of deteriorating, and he comes to view his partner as an escape from the burdens of his responsibilities.

The biggest flaws in Jack are his reluctance to accept when he is wrong and his tendency to be short-sighted when pursuing a goal. Obstacles are not a sign that his strategy may be full of mistakes, but rather they are trivial hurdles to be minimized and ignored. Jack is inclined not to give his partner's troubles the appropriate attention and assumes that they share his idealistic view of the relationship.