Am I taking too much risk staying with boyfriend who has previously had money issues

My boyfriend is really trying to turn his life around despite having a terrible record of (mis)handling money. He exhibits poor financial judgement which has exacerbated his money woes. Fast forward...he, with my advice, is doing better and pays his bills generally on time. This would be fine if I was only going to the date him the rest of my life but we are both retirement age (or getting close to it) and he wants to live with me (and marry if possible). We do get along but I just feel like I can't trust him with his $ issues because he has lied in the past and b/c of his limited finances. I'm in a different position and am posed for a comfortable retirement. I am very anxious about this issue and don't know if more time (I've been dealing with this for several years) will take care of this and even if he is finally handling his bills, etc., what happens if there is a relapse? In other words, is it (he) a lost cause??

If you really wanted to be with him, this wouldn't matter. If you really wanted to marry him, you'd not feel like he's a drain on your retirement. You'd be anxious to share the rest of your life, and everything in it, with him. I get you're trying to be practical. But if practical matters are enough to make you rethink a commitment of any sort, then why are you with him at all? Because if the idea of supporting him financially bothers you this much now, it will only get worse as you transition into retirement. My advice is; if you're not able to accept him as is, you should move on, and let him do the same. Any changes he makes to please you won't stick. You can't marry him and assume he'll change, then resent him when he doesn't. I mean, you can. But that situation never ends well.