Confident and Entrepreneurial Beggars in the U.S.

When I first came to Chicago, I was pretty shocked at the sheer number of beggars lining the streets. Basically there is one beggar every 10 metre away. (in the downtown area where I stay) This is quite a drastic change to the street scenes in Singapore whereby there are seldom homeless people, much less beggars.

Over here, beggars come in all ages and forms. I have seen a young woman dressed in stylish clothes begging for money outside a CVs store; I have seen scruffy young men seated on roadsides with signboards asking for money; I have seen old men jiggling their coins in a tin every time I walk past; I have seen women camping with their kids; even beggars with dogs asking for money to buy food for the dog.

To me, it is interesting in a sense that beggars here are quite “entrepreneurial” and “active” in their methods to get money. Sometimes the beggar holds the door for you, so that you could hopefully tip him a dollar or two. I have also met a woman who came straight to me telling me that she is hungry and needs money for food.(I thought she was approaching me to ask for directions!) There was once when my husband and I were walking along the streets and a beggar on the street commented that I look good and asked for a tip. I even met a man who approached me on the train station’s platform to sign something, and once I’ve signed it ( it was simply a paper with many many signatures), he said it means that I have to pay him.

Comparatively, if I were to spot the odd beggar or two in Singapore, or other parts of Asia, they are a lot more passive. They simply look scruffy and pathetic on the sidewalks. Come to think of it, I don’t think they even make signboards for themselves.

Recently, I met another man who gave a whole new definition to confident beggars. LOL. According to him, he sleeps on the train. He would walk along the entire train, going from cabin to cabin asking for money. Each time he enters a new cabin, he will go into a loud announcement, saying that he was kicked out of his home, that he is living on the train, and that he hopes everyone can spare him some money. ” I know I don’t look like a good person, because I have many tattoos, but I am actually a good person……”

And when no one responds to him, he will continue on and on about how he knows people don’t like to see him, and that he don’t know why no one is responding to him etc etc. Thing is, he looks like he is in his twenties and is someone totally capable of working. Second thing is, he always have a knack for making it sound like every passenger on the train ought to help him. And he does have a bit of a talent in making me feel guilty! I have met him twice, and both times when I saw him, I will quickly avert my eyes or I will pretend to sleep, haha, but in my heart I feel slightly guilty, like I am a really evil person cos I am not helping. There is this confidence and self-righteousness which is quite..hmm..special I suppose.

Until now, I am still not used to seeing so many beggars around. It makes me feel incredibly unhelpful when I don’t donate money, but I have observed that very few people really bother to maintain eye contact with them, so this is what I emulate. Even so, I still feel slightly guilty each time.

How do you respond when you walk past a beggar?