Embracing Uncertainty or Recklessness

I recently met a man in a bar. After a very short introduction, we became close friends. He is many years younger than I am and is not stable in his life. He does not have a job or a car or even a permanent home. I think he is a very nice person and I enjoyed spending time with him, but my instincts tell me he would be a big risk for me. I have two children, a brand new house and many things I have worked very hard to get.

According to the law of detachment, I am supposed to embrace uncertainty. This man tells me he has many plans for his future, yet I am skeptical to believe in his intentions. So all my instincts are telling me not to pursue a relationship with him. Yet, I wonder if there is a reason we were drawn together that night. Am I supposed to help him? Am I supposed to ignore the risks I could be putting myself and my children in with the hopes he could turn out to be the man I am looking for? I actually have a past record of relationships with men who needed a helping hand. Neither of those worked out well for me. If I do not look to my past experiences to make this choice, then I may be doomed to keep repeating it. How do I discern between letting go of the past influences in my life and making a wiser choice?