Make a list. Do a list of pros and cons, and really evaluate your job. What is your job costing you in the long run? Do you see yourself working there for the next 2, 3 years?
That’s not enough information there unrequited! To give a good answer, I’ll need to know how things are now. Is it still platonic between you two? Has she shown any signs that she feels the same way?
It sounds like you have trouble making decisions. You’re not alone in this –most people don’t like to decide where to eat, simply because it assumes responsibility for yourself and others.
Lots of things, but here’s what I’d do:
First, I’ll tell him that I’d really appreciate him paying back the money he owes me. In a serious way, not jokingly. I want him to understand that it’s no longer a laughing matter.