Has money ever came between you and a friend?

How far is too far when lending a "best friend" money? Money always seems to come between two people. Money has such a sentimental meaning although it is just really PAPER. I believe that money reflects how hard working an individual is. However, there are people out there who were handed everything growing up. I was always taught to handle my own finances and to get a job at a young age so that I can afford nice things. My best friend on the other hand, was handed everything from cars, to gas, to clothing and even money to go out. Although we have two completely opposite personalities, we always have a great time when we go out. However, it always seems that even though she works and her parents are always handing her money, she never has money when we go out and I always end up paying for her. I feel like if I say something then it might trigger a fight. The two of us have never had a fight in eight years. Its almost not worth it over something so dumb, money. Money is always the key to fights between people. She can never meet me half way in our friendship anymore and it drives me nuts. My family treats her like family and quite frankly I think that she comes over my house to hang out with them. Her family on the other hand acts cold when I am around and is really uncomfortable. Do I break ties with her after eight years? Has our friendship came to that level where we hide things that bother us from each other just so we don't get into fights?