Should I feel bad that I am not legally married?

Well you I was able to relate up until the part when you said "if I ask for a ring and he says he doesn't have the money and I know he does" my situation was that we were young and broke but everything else was the same - I didn't care about anything flashy either. I was even really content with just being engaged until the kids started school and then it became really awkward because my listen name was different from the kids. Long story short we stayed together for 12 years and in some ways I was glad when we split that we never married - there was no legal division of property and assets and shared custody was easy to agree upon. I say give him time if he knows how you feel - make a point to tell him one good time more why this is important and then let it be. However I would set a mental date in your mind and if does not propose by then you need to re-evaluate BIG time as there are real reasons why he doesn't want to marry. Honestly I wouldn't be too pushy on the subject a lot because that will only push him further from the thought of considering marriage.