Well, maybe I'm a heartless jerk, but I never pay other people's meal tabs with the exception of something small like can I grab you some coffee, and have never expected anyone to pay for me, nor would I accept it unless it would result in an argument and bad feelings,
I'm having a hard enough time in life after 2 layoffs to worry about other people and their money problems as well. Sheesh - I can't imagine someone expecting someone else to pay their bills.