my most off the wall headcanon is that despite wigfrid consistantly making mistakes like out of character remarks and having to correct her lines or narrate herself, she's still a better actress than wes is an entertainer, because even though everyone else considers them both insufferable (bar winona who's a sweetheart, and webber who also is rather kind-natured at times i guess), she still pretends to be the best at everything, and manages to get others to believe her act.while wes just does the same three hand gestures over and over at the tent when hounds are coming.
haha for real though i kinda have a weird headcanon that wilson has a crush on winona due to her interest in machines/technology
as well that wendy isn't actually physically weaker, but just doesn't hit as hard because she's more focused on abigail and mourning than killing
also that maxwell is aware of walani and the other shipwrecked exclusive characters, even in together, he just doesn't think its worth mentioning
oh, and that wickerbottom is actually afraid of sleeping, given the face she makes when she wakes up after being put to sleep unnaturally (if i had to wake up to that, i would be too, lets be real)