Ready to lose my mind and freaking out!

Been dating the same guy almost 5 years. He had financial issues arising from his business failure over a decade ago (and he was convicted of check kiting). He was able to get employment until about 5 months ago when he was laid off. He's been trying but at 65 y/o, it's not easy. He is living off of unemployment and just inherited some money($50K) but it has to be left in trust and he already owes $10K to his credit card cos. He and I do love each other (a lot) BUT I'm freaked out b/c he wants to marry me as soon as he is employed again (and he reminds me he can also collect social security as of Jan 1).

I am a professional and a widow with 2 adult kids; one of which I'm totally supporting and another slightly supporting.
I am so torn up about this - I can't sleep through a night - i really don't want to break it off with my bf but don't see how I can marry him much less live with him. even if he gets a job, I don't trust his financial judgment and he has almost nothing saved for retirement.

What would you do???

At his age of 65, financial stability is a must. It stinks to love someone so much without this, but I wouldn't continue with this relationship. Are you stable financially on your own with your supporting responsibilities?

Do you just not want to break up or do you not want your relationship to end?

Yea, there's a lot of risk here since you're helping your children and they're priority. Are there any other options you two have other than marriage so your finances aren't intertwined which would still be satisfactory for the both of you relationship wise?

From what we know here, I would still stay in the relationship, but stay away from marriage until there is enough financial stability coming from his side. There's this feeling of urgency coming from your post that is overwhelming and it may be good to think about where that feeling of urgency is coming from. Is the feeling of urgency being induced by your boyfriend because of his situation? Is there something in you that is reacting to this situation that is igniting the urgency? The urgency of the marriage is an issue. Hope this was helpful.

He wants to marry me and is saying as soon as he is employed again, he wants to do so at that time. I suppose that he feels I'm more committed that way since I have broken up with him several times due to his financial woes.
I had met someone in between the breaks who I still keep in touch with - he is an established doctor and is very nice and considerate. We get along but he lives outside the area so that is an issue for now. He has made it clear he really cares for me.
Does this change your advice?

Sounds that the marriage is there to make sure you don't leave him, not due to the constructive progress of a relationship. "I suppose that he feels I'm more committed that way since I have broken up with him several times due to his financial woes." This is the voice on control.

With this Doctor, is this person someone you may want to be with?

It looks as if, and let me know if I'm wrong and don't have enough information to take a guess on this, is that the urgency coming from your boyfriend to get married has pushed you to look elsewhere to someone who is more established and considerate. Is there an emotional battle going on between what you want in a good relationship & man verses the severe urgent feelings of getting married to your current boyfriend because he wants you to be more committed to him regardless of anything else you feel?

Let me know if I've been unclear about anything.

yes, you got it right. In a "perfect" world, if he didn't have the financial issues, I'd at least live with him and consider marriage if things worked out after living together for a while.
I also want to be settled myself but I don't want to create a difficult situation for myself. At this point, I feel like a ping pong ball going back and forth and getting no where good.