What would you have done in this situation?

A few months ago I was at a gas station standing beside my car while waiting for the pump to shut off after filling up my car. I was approached by an assuming gentleman given my immediate impression of him. I was not the least bit threatened by him, in the beginning. He proceeded to ask me a series of questions about my feelings on having a sick family member that lived out of town? What would I do if I had car trouble and could not get to that family member? What would I do if I had no money and no family in town to help me out? How would that make me feel? I wanted to be nice and I wanted to believe that he really needed help and was in a dire situation. Society has made us hard, cold and overly cautious to the point that we question every thing and every one that approaches us with these type “situations”. But honestly, I really started to feel nervous while this person was standing in front of me pleading for money. Understand this, I believe in charity and good will. I believe in helping those in need, when it is a legitimate organization. This particular situation ended with me saying that I was sorry to hear about his family member and I wished him luck. I did not open my wallet nor did I offer to fill his tank using my credit card. I got in my car and drove away. All the way to work that morning I truly questioned my actions. Let me bring you to relatively present time. I was pulling up to the gate at the apartment complex and rolled down the window to enter the code. I was sitting in my car waiting for the gate to open and turned to say something to Aubry. She pointed to the window (which was still down from when I entered the gate code) and told me there is a man standing there. I turned to see the same man that I encountered at the gas station a few months ago. He smiled and proceeded to ask me the same series of questions that he fired off the first time. While he was talking, I had my car in gear and my finger on the button to roll up the window. I told him I was sorry but I was not able to help him. I rolled up the window and left as quickly as I could. Not only was this the same story I heard before, but I had Aubry with me this time. That made me incredibly nervous. After we got inside, Aubry started asking me questions about what that was all about. I told her in very simple terms, there are people that tell lies to get money out of strangers. I told her more than just that, but in the end she learned more about strangers and a different type of danger. Now I bring you to today. This morning as I was pulling out of the complex I saw a man and a woman standing on the side of the road. There was a blue glow in this mans hand that I recognized as the light from a cell phone. He was flagging me down using the light from his phone. I almost did not stop until I recognized the same man I saw only a few days earlier. I cracked the window out of curiosity ( I know stupid, right…). Low and behold, he started with the same series of questions. I stopped him in the middle of his sentence and asked if his car had broken down, again. He looked a little shocked so I continued with, “This is the second time in the last week that I have seen you in this area. You asked me the same exact questions then as you are beginning to ask me now. You are scaring people.” I rolled up my window (which was only cracked this time) and drove off as he was left standing there wondering what just happened. How are we to know if the next person we encounter on the side of the road or at a gas station truly is in dire need when this "gentleman" is simply pushing his story on every one he sees in order to get money for goodness knows what?