When is a friendship no longer worth the effort?

I had a fight with my best friend. He said he takes more crap from me than he ever would from any girl he’s ____ing. (His words) Then he added that we like each other enough to get past this (our fight over his lack of communication wherein I asked one time-sensitive question and when I had to progress without him, I let him know that he really let me down) and he was YELLING at me. He kept saying over and over, “I’m not your boyfriend,” and he hung up on me when I interjected that his actions convey something else.
To summarize, I lent him a large sum of money 2 years ago. He recently paid it all back. I asked for a MUCH smaller loan for just one week. He told me no, then recanted and got angry when I told him he let me down.
Am I expecting too much from this friendship to ask the same thing he asked of me? Is it legal for me to punch a guy whose father is an attorney?