To believe or not and at what cost?

My bf has historically told me "white lies" about his money.

After several breakups because of his behavior, he has now come back to me once again and promised he will never lie again and further, that he is a new man and cleaned up his act. Specifically, he is very budget conscious and pays his bills on time. After some investigation of my own, I believe this is right. Of course, he has an inheritance fund to use for the larger bills but has assured me all of those are behind him and he still has $30K left as "savings". He also promised to start a savings account months ago and now has some extra money in his checking account which he says he will transfer to a regular savings account soon.

He will be 66 and wants to be exclusive and build a long term life with me. I assume that means at least living together. He is very loving and family oriented. I just don't know if I'll be conned again or not? It is possible he has finally changed and I don't need to worry about money issues on his side? He is collecting social security and has a job with a modest salary so he has more than enough to pay his bills but not a good nest egg for retirement.

He wants me to tell my kids now that "we are back together" so that he is free to tell his family and friends.
Am I kidding myself - will I end up supporting him either way even if he is truthful moving forward?