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!!!