Why can't I get over feeling unsafe financially with my boyfriend I love?

My bf and I have been dating years and he wants to move in. Being a conservative person when it comes to money and worked hard all my life and saved $ for retirement, etc., I am really troubled with his behavior. I live in a nice home as well. He earns enough to pay his regular bills but nothing extra. He did inherit some $ and used a lot of it to pay back bills so he has some left and owes no old debt (he still charges but typically pays that off monthly). He puts away $200/month but he can't manage anymore than that. I just feel like I can't trust him financially. I had to really spend time and energy and even break up with him a few times for him to change his money ways. He is much more prudent now but he still does stupid things like he insists on going to a concierge doctor that costs $1700/year and I tell him he has no medical issues and he can't afford it but this was his original doctor and he likes the convenience he says. He also hasn't asked for a raise since he started work over a year ago even though he is now running the store for the business - his friend owns the business and gave him a job since he was unemployed before that and at his age (mid 60s), nothing was coming his way. He even didn't put all of the inherited money into savings and left some $ in his checking account but I can't figure out why (he claims it's for his mother who went into a nursing home and he'll transfer it at months' end, but that makes no sense since she is on Medicaid). I step up and sometimes pay for things which are his sole responsibility just to see if he'll save more but he doesn't. He says he'll pay me rent and if it's less than he pays now, we can put it into the savings account to spend for vacations and the like (although it won't amount to that much I think). Basically, I feel like I"m subsidizing his living expenses. For the same amount or less, he will be living in a beautiful home rather than a one bedroom apt. I may not mind sacrificing to have him in my life, but I feel he isn't sacrificing enough? Am I wrong? I recognize we love each other and he is a good man and is family oriented, but am I being taken advantage of? I'm not that desperate even though I know at my age, the good men are in short supply. Am I being too critical and paranoid in thinking he can't be depended on when he lives with me?

I first want to say thank you for sharing your personal story with me and to the rest of the community. I think that you have some valid reasons on your frustration and feeling like you are being taken advantage. However, I do want to say that it really is up to you if you want to continue this financial path with him or not. He clearly does not make as much money as you and it sounds like from what you wrote in your post you had to break up with him a couple times for him to get it. I think that you may want to work out a budget plan with him. I suggest looking at some you tube videos (Couples budgeting together) they have some really cool and fun ways to work as a team to save money on both sides. I did that with my prior gf and it worked out well. However, if he is not willing to pursue these types of ideas and continuously spends money in the wrong ways than you might need to tell him that it might be best to go on a different journey your money is as important as his and especially if your taking more of the weight spend because your job pays more that is something he needs to understand. I hope this helped. How do you feel about what I said? Take Care and Best of Luck!

Thanks for that advice. The only other sticking point is that he is almost 67 yrs old, so he can work indefinitely so long as his health stays in place - which is another risk.