Last time I was in Chicago I was approached by a hustler almost immediately after I got out of the parking garage. He gave me the typical spiel about his family being down the block and he was out of money. Not out of the ordinary for Chicago.

We engaged in small talk for a minute. After I put a $5 in his hand, he began to break down and explain that I was the "first white person" to talk to him all day. He went on to imply that "white people" are afraid of him (he's black). At the end of our exchange, he asked me for a hug and I reciprocated. He told me he'd pray for me and I wished him well.

Maybe it was all bullshit, but it brightened my entire day.

In my experience, because people got shit to do, whoch is why they're downtown.

Re: your new friend, the hustler.

You're a special person, because the standard reaction to that kind of person is to walk around them without making eye contact. I commuted through downtown daily, and I got to recognizing the hustlers pulling out the same rehearsed stories over and over again.

Of course, you definitely don't want to become as much of a cynic as me :)