Why do I keep myself in danger?

Continuing to work when you'd rather be retired stinks. So I am not without sympathy.

That having been said, what is he doing to try to get work? Sending out resumes? Taking a class to add new skills or update existing ones? Networking at industry events? Meeting with an employment counselor? Hanging out his freelancing shingle at places like Upwork? Visiting the union hall?

If he's trying and there is just nothing out there, that's one thing. But if he's not, then his situation is mainly of his own making.

Either way, you are not responsible for him financially. You can be kind, of course, and pay for dinners or go to less expensive places or be content with free dates. You can be supportive of his struggles and even drive him to job interviews if you like.

But you don't have to shell out his rent money, or give him a roof, or marry him to get him medical benefits. You don't have to buy him groceries, either.

And even if he is trying really hard to find work and is just plain unsuccessful (it happens), then you are still looking at someone whose remaining years are more likely to have medical issues than not.

I'm not saying you should be mean, but you are in a position, currently, where you are not as fully wrapped up as you could be. Of course any of us could be hit by a bus tomorrow. But guys who are over 65 years old and who have the stress of no employment prospects probably don't have terribly long life expectancies. And those years might not be so kind (stress can lead to strokes, heart attacks, etc.).

You say you have adult kids who need your help. I am assuming you are willing to help them. Well, the bucks aren't infinite.

Choose.

thank you

It's human nature (for most folks) to want to help people out. The trick is to forget that you've gotta take care of yourself first.

I understand you don't want to bail on this guy during a tough time, but don't feel guilty for managing your own stressors. Would it be possible to slow down the relationship so that you guys can just go out once or twice a week, not live together or anything like that, but JUST date?

Trust your instincts.

You don't want to enter your retirement years takung care of a man.

Just date. Keep things very separate. Don't put yourself in stress at your age.