Ah yes - 'Trouble always comes in bunches', is it?

[He takes a sip of his own tea, thinking before he next speaks.]

I have certainly felt like that before, myself. It's not a pleasant place to be for any period of time, and even worse when it feels like you have nothing solid to hold onto.

[He's not going to outright ask her - letting her spill the issue, but making it clear he understands and wants to help, but he respects her enough to allow her to do it on her own time.]