Tonight I was walking home from my little excursion out and about in the finally cool Chicago night. A trip to Target and the Thai/Sushi place around the corner were on my list of activities, followed by Project Runway and YouTube videos. Walking through my neighborhood can be a really mixed bag. I live in Uptown, Chicago. It is the neighborhood just north of Buena Park, a magical place of single family homes, large trees, highrises that overlook the lake and big dogs and SUVs (but isn’t Andersonville). Uptown isn’t anything like that.

In fact, Uptown is one of the ghettos of the Northside of Chicago. It has been described as “Roaring 20’s charm meets psych ward with no walls” It doesn’t take long to figure out why, nor does it take much time to generate a lifetime of stories just walking through, and I’m going on my second year here.

While there are some regular neighborhood street people, we also get a lot of traffic from new street people just passing through, or wandering though. They seem to pass slowly sometimes. There was a new crackhead that approached me one night on my walk home and asked for money, I said I didn’t have any, and he followed up with, “You’re gay, right?”

Now, I fully admit that on occasion when I open my mouth, a purse may have the tendency to come tumbling out. However, I don’t normally feel like saying “nope, sorry buddy” is going to give me away, especially when I’m in jeans and a hoodie. Either way, against my better judgement, I stopped and said yes.

Then he took my hand, like he was going to shake it, pulled me close to him and threw his other arm around me in one fell swoop and gave me a quick hug. It was at this point I realized, this could make for a seriously dangerous situation. Although I’m big and look intimidating (or so i’ve been told), I have never been in a fight in my life and I know that crackheads are crazy strong and kind of wily, and I could really be in for it. He pulls away and says “Man, I just love the gays! You guys are really cool, and I get the BEST rock from Boystown. Have a great night!”

I walk the next two blocks home thinking about what could have jumped from his coat to my hoodie in the quick exchange, and try to remember if scabies can be transmitted through a handshake. Thank goodness for loofas.

Most of the stories and the experiences are harmless enough, especially after you learn how to deal with crackheads. One thing I haven’t quite figured out yet, is how one of lady crackheads always has matching outfits on when I see her. I mean, I have yet to see her repeat an outfit and I just don’t know how she does it. I can’t even do that. And yes, she is crazy, raving and yelling and shaking every time I see her. At least she never asks for money, maybe she makes clothes. Dunno. Not all the locals are quite as passive though.

One of them, a man who looks to be in his 50’s is usually around somewhere. I see him travel with a small band of friends off and on. But mostly he sits right outside the parking lot to Jewel Osco (my local grocer) and shakes a Big Gulp cup with some change in it as people walk by. I’ve never heard him say anything, he just sits on the sidewalk and sways as he shakes his cup. He is tall, unshaven and unlike his lady counterpart, is dirty and looks sad and tired.

One day I saw a very clean lanky hipster guy in his 20’s walking near him and trying to hold small talk conversation. The man wasn’t really interested in what the kid had to say, but something struck me about them and I slowed my walk and watched for a minute. Had this hipster taken an interest in this homeless man? Was he trying to get a story out of him? Figure out why he was on the street? Maybe offer a little help? As I got closer I figured out what it was that struck me and why they were chatting.

The hipster was a younger, clean version of the homeless guy. It was his son. They neared a car and the man told the hipster he didn’t want to keep him any longer and that he should get going. The hipster reached in for a hug which the man halfheartedly gave and started to walk away as his son told him he loved him. No response, the man had already turned his back, just a small wave as he went back to his spot on the sidewalk as his son watched, pulled on his sunglasses, got into his car and drove away.

That broke my heart.

I’m not the only one. Ambulances and police cars tear though this neighborhood on a very regular basis. Police usually go a block or two north of my building to deal with the latest shooting or drug bust. Ambulances pick up the people who thought the rock from Boystown was great and couldn’t quite get enough, until their body decided otherwise. Uptown isn’t for the faint of heart. It seems like it gets better for a while, a new restaurant will open, or yoga studio to cater to the hipsters who think they want to call this “up and coming” neighborhood home. Families who come for the cheap and large apartments close to the lake in a place near great areas. Then, comes summer, people go a little nutty from the heat, the familiar popping sound of gunshots somewhere in the vicinity and all of a sudden, open apartments again. For now, it’s home and I’m staying put. I do like adventure after all.


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