Sylvia’s not always good at giving comfort when Wander is distressed (think of The Helper and The Heebie Jeebies), but she always tries her best and Wander knows she’s trying her best, and it can look like she’s being insensitive to his feelings, but he trusts her enough to know that’s not her intention at all.
In the two mentioned episodes, I think the case is that she’s hoping her calm and positive mood will rub off on him.
The Box was where she was best at helping him through one of these hard times, and that was because there were actually specific actions she could take (delivering the box as fast as possible, and then making something get put in the box for Wander to see).
The Bad Hatter is somewhere in between, because there was an action she thought to take (helping Wander pick out a new hat), but it didn’t work out because he only wanted his hat (though he did get it back in the end anyway).
And then we have The Flower, where she spends the whole episode trying to do things to make his sadness go away, because she was thinking of it like it was a bad thing for him to be sad, until he had to tell her it isn’t.
Even if she doesn’t always know the right things to do for him, she never ever gives up on her best friend and he appreciates everything she does for him.
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