I'm going to tell a semi-desperate friend to pay me
Why do that to him now?
Because he owes me lots of money and I feel entitled to it
It does belong to you. Do you really need it right away? They seem to be in a really bad position.
I'm being a good friend to pay my debts. I can't help it if he couldn't make me the same.
It might be good to show him some mercy right now and try to set up a payment plan or a deadline. He might have problems paying rent or a car payment and returning everything at once would make them homeless.