Hi Ennie.
Have been in your shoes more than once and it's def uncomfortable. In my experience it's absolutely VITAL to ask those financial questions: You are inquiring to get a clear picture of what and how the financial need came about and the best way to resolve it; also, whether or not it's likely to be a recurring one. IMO specifics are not too much to ask; the other person is asking you for a very personal response to their need, after all. And tho I know it can be intimidating, please don't be afraid to say "No".

Best,

Chyia, wishing you luck