Why do I keep myself in financial danger with BR?

Long story short: dating man for 5 years but he never had any real financial sense. He is now unemployed with no prospects and over 65 years old. I am very financially sound but have adult kids who need my help so I'm still working at 60 y/o. We love each other but I see red flags all over the place. I know he is really trying to get a job and he inherited some money (but a modest amount) but I've been waiting for 6 months and nothing has changed (except his unemployment will run out next month). I know I should break things off but also know it will be really painful and I'll miss him terribly. I just can't seem to do what I need to do to get myself out of harm's way with him b/c I know I'll end up supporting him at least in part but he is such a good man and a great boyfriend otherwise. HELP!!!

I think finances are more and more important as we get older. In your position, you need to be more selfish. Unless you have a ton of excess cash, don't support others. I would also assume your adult kids have jobs and families, so why do you need to support them?

Love should be more important than money.... but that doesn't mean money ISN'T important. You do your best to prepare during the good times and hope you are able to make it through the bad times. Really, this comes down to a number of factors. Just some of them off the top of my head....

How important is his financial situation to you? Right or wrong, if you can't be with somebody who isn't financially sound, then you'd only make it worse for both of you by trying to force yourself to stay with him. Is he honestly actively trying to better his situation? That can certainly make a big difference too. What if you two had moved forward in your relationship, became very close, even gotten married.... Things were fine financially.... but then suddenly he loses his job? Would you divorce him just because he lost his job? I'd hope not.... but maybe you would if he lost his job and then showed no serious effort to improve the situation.

So, it isn't a black and white situation. If there is a high likelihood he could wind up just pulling you down financially, then maybe that is your answer. If you love him enough and you think you two could still be fine financially if not ideal... then maybe that is your answer. So, it is really hard for me to comment not being closer to the situation to know enough of the specifics. I hope I've at least helped you to kind of think it out a bit in your own head. Money isn't the most important thing in the world, and love certainly should be more important. BUT, again, like I said, that doesn't mean money ISN'T important. It is VERY important. So, you don't just fall in love and decide "Okay, then I'm not even going to worry about money at all because I have love and that is all I need." You hope for the best but prepare for the worst. So, if I were you, I coul see myself going either way, just depending upon a lot of specific details that I guess only you would know.

Good luck to you. Certainly not an easy decision you have to make. I wish you the best in deciding with you think is right for you.