I find myself totally conflicted writing this note.

On the one hand, I have no expectation of a positive outcome. But on the other, I'm in a financial position where I need any help I can get – just as you were when I loaned you money or paid for things for you quite some time ago.

I understand that you may have crises, stress, or other priorities right now, but I'd ask you to consider whether it's the right thing to do to use those or the fact we have drifted apart as an excuse to avoid acknowledging your debt to me and agreeing some basis for repayment.

I have my own records of the amounts I believe I loaned to you but would rather not just repeat that here as you will simply see this as a debt collection demand rather than a plea for you to do the right thing. I accept that your view of what you owe may differ from mine, but I would appreciate a summary of what you believe you do owe and any repayments you have already made. That and how you intend to make some repayments will go a long way to fixing a very disappointing situation with someone who was once a close friend.  

If I were a millionaire, I wouldn't be hassling you and I would just put this all down to experience, but I'm not and I can't.