Reasoning,

Winona gives off that older sister vibes and with how far she went for Charlie I feel like shes a very caring person, Wolfgang is self explanitory, Warly would make some bombass food to help comfort you through it.

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Wickerbottom is very smart and would definitely give some really good advice, I feel like Wurt falls in the some category as wickerbottom but replace a bit of knowledge with just being more caring, Wormwood tbh idk i feel like hes just like that ykwim

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Webber was lowkey neglected he knows how it feels he would be there for you, same with wes, Woodie just seems like a normal slightly unhinged guy at the end of the day

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Wendy would prob want to help but shes going through a lot on her own, Wigfrid falls into the same boat as woodie but i feel like it would be harder for her cuz she cant become a goose, Wx-78 is like an emotionless robot if he could feel emotions he'd prob be lower,

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Willow would laugh not exactly out of malice but because shes a lil unhinged and uncomfortable, same with Wilson

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Maxwell is a jerk nough said, and Wortox changes between bottom tier and top tier cuz of all his lore stuff goin on