Living a double life and it needs to end!

I’m typically a very decisive individual. I am already past middle age and I have been a widow for about 7 years. The first man I dated is someone I knew almost 30 years before my late husband passed and he also knew my late husband. It has been a difficult relationship because I haven't been comfortable with what I see as his financial irresponsibility. Needless to say this is in direct contradiction to the way I handle my financial affairs. In addition unlike me, he doesn’t have much money to his name and he is already collecting social security. While he is also working that helps in terms of paying his expenses but there’s very little left for retirement. Because of all of the differences and the fact that we argued from time to time my adult son is very against me ever seeing him again. My daughter lives out of town and she did not think he was compatible with me although I know she doesn't want me to be alone and is aware I've dated several men. My son witnessed me arguing with my boyfriend and leading to several break ups. He says he cannot get over this and does not want me to date him again. I’ve hid our relationship from some family and friends because I know they’ll tell me “I can do better”. I’ve dated other men who are financially settled like me but just never developed deep feelings for them and I found they weren't always as generous as I was. Last break up with original bf was earlier this year and we started seeing each other about a month ago after he he saw me on a dating site. It appears he got his life together and is making better financial decisions although time will tell. I took my boyfriend away for his birthday. He’s telling me that he will not tell anyone in his family or friends that we are dating again unless I tell both my children immediately since I hid the relationship from my kids until I was sure I was comfortable he and I would be together in the future but after reconciling before he would tell his family and friends and then we would break up so that has been in a embarrassment for him. My question is do I not date him even though I feel deeply for him because I do know in my heart that there is some compatibility issues for retirement and because I’m very very close with my son and I don’t want to see him unhappy. I realize I have to live my own life but my son has lost his father and he has no girlfriend he also has Asperger's syndrome so he is very dependent on me sometimes. Part of me wants to just tell my kids this is the way it is I know it’s a gamble but it’s my gamble to take because it’s my life. But the other part of me feels that perhaps I should just not take the chance since the kids my kids are all I have left in this world and I know that if we live together which is very likely, I may end up "paying the price". I cannot continue to live a double life since I did that before and I know that it hurts me and also really hurts my boyfriend. I saw tears in his eyes yesterday when he was pleading with me to tell my kids are ready so that he is free to share our trip and relationship once again with his family and friends. I really do care for him and I know he does for me although I don’t know what the future holds. What thoughts do you have?