I am a middle-aged single female who has been dating a man for about five years my junior. He's a great guy, has excellent values and is a family man. But here's the problem. He can't afford to buy a ring. I'm not materialistic at all. However, I am wondering if his inability to purchase a ring is a sign that maybe there will be other financial issues down the line since we met he has lost two jobs his car, and his house all because he is pursuing entrepreneurship which is currently not thriving. I have a Ph.D. and a great job at home, and I'm doing pretty well for myself. About three years ago, I received a huge bonus check, and he stated whatever came to either of us would be both of ours and he asked me if he could use some of the money to buy me a ring. I thought that was crazy. I know that he's trying to get on his feet, but it is draining to have to deal with this for so long. So here we are three years later and he's still working towards purchasing the ring. I've been patient with him, paid his bills, and allowed him to use my car to give him gas money, but I'm tired of extending my resources. Am I settling for someone who may just be a taker, or is it possible that he's just having a bad six-year break? Totally confused.