It's entirely possible that Pandora doesn't get asked such things all that often.
Drawing people crying difficult. I was going to say "in a simple style" is difficult, but really, I can't imagine it's that easy in any style. It's just a bit difficult to do.
Things were made a big simpler for me in this comic by simple virtue of it not being intended to be subtle. The magic dam might still be up, but Pandora's emotional dam has burst.
...Was that metaphor tortured? Oh, whatever. There's a dam of some sort in the story and someone started crying after holding it back. I had no choice.