I know what you mean... You can simply just say, " money is tight right now for me. Do you have that $300 I lent you a few months ago? I'm desperate right now" Lol you could be lowering your standards a little, but it worked for me.
Everyone likes a sad story.
It was your money, you should be scared of being a bad guy for asking. Just simply ask him. Don't drop hints.
Tell him you understand he has money problems but you want the money back. He may have some of it rigt now and may be waiting until he has it all. If you dnt ask about it he may forget about you lending it.
He may have even conned you. Good luck.
I cant really gove you an answer,but what I can give you is a way to a solution, that is you have to find the anglde that you relate to or peaks your interest. A good paper is one that people get drawn into because it reaches them ln some way.As for me WW11 to me, I think of the holocaust and the effect it had on the survivors, their families and those who stood by and did nothing until it was too late.