Kenny and Gladiolus

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Kenny and Glad are enemies to friends

Here's how I imagine it go with all my hcs:

Kenny, when first joining the group, thought that Glad was stuck up, better then the rest of them, etc. Kenny would sometimes even call him names (although it was rare), but one night, when he was passing through a room, he heard Gladiolus talking to himself about his past trauma, with how rich to how he was to how he was basically neglected, and had a bunch of expectations put onto him. Kenny obviously didn't know about it, as it was private, and randomly entered the room to give Glad a hug. This started weekly venting day where each can vent about whatever they wanted to vent about, and they often hug each other. It's mostly Glad who vents, even though it isn't much, Kenny can tell how sad he was when he was younger, and hugs him.

Edit: I'm changing things so I can make it more canon, even if this is a headcanon book, I'm willing to change things so it can be canon

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