You're not selfish one bit. I for one wouldn't want to be tricked out of all my money for someone who was supposed to love me. I suggest if you do end up getting married, get a pre-nup. That way what you have before you marry him, you'll still have if he leaves you and he wont get one penny from you.
If his goal was a tree house, a guitar and a barefoot pilgrimage to India... I'd say go for it! However, since his dreams require money, drive and dependable reliability and he is doing nothing to make his dreams come true besides figuring out what he could do with YOUR money... I think it is time to cut him loose to find his next sugar momma.
He must be incredibly hot in bed because for the life of me I cannot understand how a level-headed, financially responsible, goal-oriented, planner has stayed matched with a spur of the moment, non-goal, financially irresponsible, bubble headed guy this long. Please don't tell me he completes you.He has had 3 years to get his head on straight, join the club, and create a goal. Instead he seems to still be the same kind of guy so while he has stayed in a state of flux, you are growing, working, planning, becoming affluent. I think it might be time to do the old pro and con list making technique because I don't see this going any where. You've invested in a lot of things that have paid off. This seems to be only one that you have not profited from.It might be your gut is arriving at this same line of thought. Time to quiet yourself and listen to it. Good luck!
You have been in this relationship for three years and you still don't trust him? Really? In cases like this I say go straight with your gut. If you feel in your heart that this man is using you, you need to get out asap. If you feel that he really wants you for you, then get your head out of your butt, because you have a good thing going. A word of advice though, if you spend your whole life clinging to your money and thinking that "assets" are the only thing a man sees in you, you are going to have a lonely life with your fancy portfolio. Good luck honey.
Love is blind - but not in your case. If he, in fact, loves you and asks to marry you I think you should have him sign a prenuptial agreement. Keep everything in your name (don't refinance your house and put his name on the deed etc.). Talk to a lawyer and find out about the in's and outs of common property. You may not be able to keep your accounts and assets separate. If you are willing to support him into retirement for the benefit of having a man around, then go for it.
If u do not want to share your life with him no matter what for no matter how long period - you do not love him and maybe you should not be together. Also there is a prenuptial agreement option. And why can not he live with you in your house if you say you have one? And you do not need to get officially married anyway - just live together for several years and you will see whether he is with you for your money and assets or because he loves you.
I would ask him straight up. Say honey, I feel you only want me for what I can bring to the table financially. Gauge his reaction. What ever he says tell him your investments are now gone (retirement was put in the stock market or whatever would plausibly make you broke) then see what he says. You should get a clear answer if he thinks you are now broke. I dated a man (long ago) that was extremely rich and I didn't know it till three months into the relationship. He wore torn jeans, drove an old car and took me on many cheap dates for coffee. Never occurred me that he had money. Didn't know till he showed up at my home in a new car, dressed to the nines with a dress in a box for me to wear to dinner to (a very nice restaurant). He had learned the hard way that many women only liked him for his money. He wanted to make sure I liked him for him. You need to do the same thing. Make him think you are broke. If he says okay we both will just live for today, ask yourself if that is how you want to live with his attitude? Personally, I rarely let anyone know that I have money till I know them very well. I'm not talking big money but owning my own home, modest investments and retirement. Three years is a long investment and I'm saddened that you don't clearly know by now if he is in it for you or what you can provide.