I wonder if you asked them in a different way if you would get a different response. When you give them a 5 and then are asking "what is your story" or "are you homeless" that puts them on the defensive in a way. I am thinking of a way to put it that sounds inviting. Perhaps if you tell them that you earned this money from people who don't even know you so that you can pass it on to someone in need. I feel your need and wish to give this gift to you. Then wait and see what they say just be with them in that moment and enjoy the feeling of giving. See them with Light and Love and then be ready to hear a story or move on... This may be a fun thing to try.
I upvote you for doing this I think what your are doing is beautiful.
Looking forward to future of your journey of synchronicity.@einarkuusk when that song started to play tears came to my eyes. @unityeagle listen to this beautiful song in his video so beautiful.