Thanks @cabel! Can't wait to see it on my physical Playdate 
@orkn -- Neat idea, but unfortunately the dialogue box always gets drawn on top, as far as I can tell.
Which reminds me, I noticed that the player sprite also gets drawn on top. So if the player happens to be standing in that 5x5 grid, they'll break the portrait. That could be solved by calling the hide function when the player happens to be within that range, but I haven't tried it myself yet.
