In Chicago, you can’t walk down any street without having multiple people asking you for money or food.  Often the same panhandlers on the same corners saying the same things.  Fairly regularly when riding on the L, someone walks through your train car, telling you some sob story about medical bills and asking for money to help them out.  If you’re lucky, you might see a busker sharing a gift and I typically throw a couple bucks into their guitar case or bucket.

I consider myself a fairly considerate person.  I’m not opposed to helping.  Like most people, I’m giving of my time to those who need it and I give generously to organizations that are giving back to the community.  And I always buy a Streetwise when I see someone selling them, even if I already have a copy.

But I am opposed to this feeling of obligation, that somehow I owe money to every person with their hand out.  I can’t help feeling there’s something most of them could be doing (see Streetwise above), that they’re taking the easy way out, that they’re probably just spending it on booze.

I’m bothered by the tent cities that always seem to appear in the northern neighborhoods under Lakeshore Drive where I can afford to live but somehow are never found near the Gold Coast.  I don’t like a public sidewalk that is my only option to get to the public lakefront also serving as the front yard of a bunch of people living in tents.

This is different from when I first moved to the city and wanted to make sandwiches to take down to the underpass, when I’d happily share the few bucks I had left believing that somehow there was a karmic ripple that would help.  Now I’ve learned to always have a book on the L.  I’ve learned to walk with my ear buds in, music drowning out the din.  I’ve learned to ignore and avoid.  I’ve learned the quick and easy excuses to say when none of those techniques work.  “I’m sorry, I don’t carry cash,” being my favorite line.

Because to take it all in, invites an overwhelming feeling that no matter what I do, I cannot make a difference.  Sure I recognize there are reasons the tent cities are near the north side.  I know there used to be a lot more funding and facilities there that were closed down, causing a lot of people with very real mental conditions having to fend for themselves on the streets.  I can’t imagine what life must be like for those in the tent city and how a community, under a roof of sorts, can give a person some semblance of  safety.

This is my experience.  And so, when I sat down to enjoy my blueberry, bourbon, vanilla donut at Blue Star Donuts in Portland and saw a homeless guy swiftly approaching the store, my Chicago mentality kicked in and I immediately became immersed in my phone.

But he wasn’t interested in me.

“Yo, where my boy at?” he asked the guy behind the counter.

“He’s not here today.  You want me to get you some donuts?”

“Yes ok.  Thanks man.”

I’d had difficulty deciding between the various gourmet options when I’d ordered and I could hear him going through the same struggle.

“I’ll take one of them cointreau creme ones.  Is that how you say it?” he asked.

“Yup that’s right.”

“And how about a maple bacon too?  Are they both free?”

“Sure are.”

“You need the windows cleaned today?”

“Nope man you don’t need to worry about that today.  All you need to do is enjoy those donuts.”

“Thanks,” the guy said and he walked out.  Again paying me no attention.

I watched him furtively from behind the safety of my sunglasses as he took one of his donuts out of the box and took a bite.  He smiled at two young women enjoying their donuts and they exchanged a few pleasantries and smiles.  And then he went on his way, a bounce in his step.

He belonged.  I was the outsider, the person living on the fringe.  They were regular citizens who all just happened to like donuts.  I wanted to be the girl the homeless guy had exchanged pleasantries with.  That would have made for a better story.  But my sunglasses were on and I was the asshole.

After devouring two donuts, because I too couldn’t decide, I headed to a cafe to write.  As I sat down, I could see two pan handlers getting ready to work a corner.  Both were smiling, yelling at friends across the street, looking around and sizing things up before finally beginning to approach people as they walked past.

Almost every person who passed them, even those in groups, stopped to talk.  One girl put a hand on one of the guy’s shoulders companionably as they chatted.  I saw pockets being emptied for spare change and people handing over bills, sometimes multiple hands reaching out, one over the other at the same time.  Nobody seemed put out by the requests, all seemed eager to help or at the very least have a human conversation.

I felt like I’d entered some alternate universe where hip Pod People happily handed hard earned money and donuts over to anyone who asked.  How could people with so little sun be so damn nice?  I also felt that somehow those panhandlers were taking advantage of them.  But can you take advantage of people who seem to be happy to give?

By the time I left the cafe, the panhandlers had acquired enough cash for whatever they were looking for and had headed off down the street.  But I was approached by a young kid with a box of candy that he was selling so some team he was on could go somewhere.  I happily forked over cash.  I felt somehow cooler.  It certainly alleviated some guilt.

Since this event, I was able to chat more deeply with locals about the homeless in Portland and have found there’s another side to things.  It seems that there are a lot of transients coming through Oregon and Portland in particular and that they can get quite aggressive with their panhandling, especially downtown.  Refusing to hand over a cigarette or a couple bucks has gotten people pushed off the street and into traffic.

Their take on it was this aggressiveness started when Oregon passed some sort of law that protects the rights of freedom of speech.  So aggressive panhandling is protect under that and while Portland as a whole seems a very loving and giving community, the huge influx of transients is becoming an issue that will have to be addressed.

We’ve got a lot of issues going on today that need to be addressed in general and I wish I knew what the answers were.  Like most of us, I only seem to be able to say what the answers aren’t.  I don’t think it’s earbuds and sunglasses.  But I also don’t think it’s as simple as handing over money.

I wish I had a poignant “aha” moment to end this blog post on, but I don’t.  I do know this is a journey of discovery though and I’m hopeful maybe I’ll figure some of this out before it’s complete.

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