I dont know if I am the only one who sees this but I see her as entitled and abusive. Emotionally abusive for dumping you all the time (you are a little complicit due to the fact that you keep getting back to her). That kind of emotional back and forth is very harmful and very mean. Expecting you to be ok with handing her money and then bargaining for how she should pay you back is unacceptable. If I borrow money from a bank I do not get to pay it back in lolipops. I have to pay them back with money. You go out to eat and then at the end she asks if it counted towards paying you back so really you only got half your money back because she ate too. I would recommend you get in to see a therapist to figure out what is it about you that would allow you to put up with behavior like this from someone who is supposed to care about you. I would recommend trying to figure out a way to break up with her as painlessly as possible.