Dear Prudence,
I have a good friend who struggles financially. He keeps his rent money in a PayPal account; every month, his sister withdraws the amount of his rent from her own account and delivers him the cash, and he sends her the PayPal amount. When his sister can’t for some unforeseen reason, I get calls asking me to do it. He says it’s to prevent his bills from being auto-withdrawn from his rent amount, but I find the whole situation weird. Once, he didn’t ask, he just sent the money via PayPal and begged me to get it to him that night. He has a habit of assuming I will do him favors without asking, which bugs me like crazy. But I don’t want to be responsible for him losing his housing (especially since he was homeless briefly this year).