Weekend in the Windy City

Not long after I started my new position, an opportunity came up for a training workshop in Chicago. Chicago happened to top the list of U.S. cities I hadn't been to that I wanted to visit, so I jumped at the chance. I just got back today. The meeting was yesterday and today, but I flew out on Friday to have a couple extra days to see the city.

I had a great time. Explored Millennium Park and saw the Cloud Gate (the big reflective bean-shaped structure from the end of "Source Code"). Rented a bike and rode along Lake Michigan (so huge, it looks like the ocean). Randomly came upon a bookstore where Jane Lynch (of Glee fame) was signing books (the line was too long, but I did catch a glimpse of her through the window). Saw sketch comedy and the Second City theater and improvisational comedy (my favorite kind) at the Improv Olympic Theater.

But the most interesting thing I did? Well . . .

I had heard from a friend that went to school in Chicago that his former community, Lakeview, was a nice area to visit. He also mentioned that there were a number of gay bars in the neighborhood (as in, be careful what bar you go into). I looked up Lakeview on the internet and discovered that a region of it, specifically that bordered by Halsted, Broadway, and Belmont Streets, is known as Boystown, and is the city's primary gay district. It turned out that one of the closest subway stops, the Addison stop of the Red Line, was also the stop for the Improv Olympic theater. So before the show on Saturday night, I ended up walking down Halsted Street to survey the area. I went into a little store called Gay Mart, which strangely seems to primarily sell comic book character action figures. I browsed around for a bit, and since I didn't spontaneously burst into flames or anything I decided to continue my exploration. I visited The Center on Halsted, which is a community center geared to the LGBT community (but open to anyone). It's connected to a Whole Foods, so I got dinner there and ate it in the Center's dining area while reading a copy of The Windy City Times, a LGBT newspaper.

THEN, I decided to do the unthinkable. I went into Roscoe's, a real life gay bar. And I ordered a drink. And I drank it. In the gay bar.

I didn't talk to anyone, I just sort of walked around, exploring the place, then quietly finished my drink before heading for the show. But still, wow.

And after the show? I went back. Because it was still relatively early, and I figured, what the hell. I got another drink, and this time the place was packed. There seemed to be a mix of gay and straight people, which somehow made me feel better. It was still awkward, but this time someone noticed me. Two guys who were together walked by me. One grabbed my arm and gave it a squeeze. The next guy ran a finger down my sideburn and gave me a thumbs up as he walked away. Not sure if he was being sarcastic or not (my sideburns are kind of long right now). Whatever he meant, it made me a bit self-conscious, haha.

To distract myself from the awkwardness, I watched the music video playing on the screen up and to the left of me. An older guy walked in front of me, and out of the corner of my eye I could see him look at me. I continued to look at the screen. He looked again. And again. Then he touched my shoulder to get my attention and asked, "What are you looking at?" with a smile. Embarrassed (and caught in my lame attempt to avoid his gaze), I mumbled "the screen" and pointed at the TV. He chuckled and walked away. Um, yeah. Anyways, I had achieved my goal of setting foot in a gay bar. So the next goal would be talking to someone in one (that didn't count).

Monday night was my last night in Chicago. There was a dinner for the meeting, which got out at 9 PM. Since the night was still young, I decided to visit Roscoe's one more time. My subway pass had expired, and the machines don't give change, so I had to walk around the downtown area to find an open store and break my $20. By the time I got back to the subway, it was getting late and I was having second thoughts about whether it was worth it to go all the way back up to Lakeview at this time of night. I didn't know whether there'd be many people out and about, being a weekday night, and I was concerned about safety. In the end, I decided to at least go for it, and turn around if at any point I felt unsafe.

When I got to Roscoe's, I was pleased to hear the sound of live music. I LOVE live music. And it was ROCK MUSIC! And it was a QUEEN song!!! Specifically, "Fat Bottomed Girls." As it turns out, Monday nights at Roscoe's are Live Band Karaoke nights. Which means, a live band provides the music and you go up and sing the song. A bar near where I live does something similar, but I hadn't had a chance to go yet. So finally I got to see what Live Band Karaoke was like. I checked out the band's list, and it was amazing. I looked for a song that I'd be confident enough to sing (considering "Hunger Strike" by Temple of the Dog, or something by Pearl Jam or STP, yep I love me some grunge), but in the end I couldn't get myself to do it. It took enough nerve just stepping into that bar.

However, a couple of guys had seen me studying the list. One of them was a really good looking guy who had done "Brown Eyed Girl" earlier. The other, I believe, was his brother (if I had overheard correctly). They asked me what I was singing, and joked that because I had looked at the list I was obligated to sing. The cute one added, "Or you'll be shunned, you'll be exiled." Seeing this as an opportunity to open up conversation, I responded, "Well, I'm leaving Chicago tomorrow so I guess that doesn't matter." He said, "Oh, me too!" High five. Turns out he was from Texas, and was in town to run in the Chicago marathon. I asked him how that was, and he said "Crazy, worse than crazy." Then he resumed his conversation with his brother and some other people.

Later on this creepy older guy started going around to different guys in the bar and getting all touchy-feeley. Several times he came to the Texan and did that, but the Texan would push his arm away whenever he tried to put it around his neck. Finally, after that had happened a couple times, the Texan got up and cussed him out. Creepy guy made a swift departure from the bar at that point. At this point I'm still not sure if the Texan was gay, or was just there with his gay brother. Whatever the case may be, he was really attractive. I felt good that I had already accomplished my next goal of having a conversation (albeit a short one) in the bar. Before I left I said good-bye to the Texan (who gave me another high five).

One of the most remarkable things about my visits to Boystown was how I was able to somewhat get over my self-consciousness. With me being there, it would be a natural reaction for anyone to look at me and assume I was gay. But the anonymity I felt made that okay. No one in the whole city knew who I was.

Another test came today, when I stopped in a bookshop at O'Hare airport and picked up Ricky Martin's autobiography. I wondered what the cashier thought about me buying that book. Anyways, his story interests me, since he struggled with his sexuality well into his 30s. A late-bloomer, if you will. I'm not as old as him, but that doesn't stop me from feeling like a late-bloomer too. The whole time I was in Boston, every time I noticed a hot guy (usually in the early to mid-20s range), I wished I had reached the point I'm at now when I was 22. Sure, just 5 short years ago. But I wish I still had the bulk of my twenties ahead of me (plus I wish I'd actually accomplished my bulking up goals). I'm still not sure where this path will lead, if I will continue to pursue the possibility of dating the same sex. But this weekend, with my checking out hot guys around Chicago and visiting a gay bar (on two separate nights), definitely didn't rule it out. My experience, though awkward at times, wasn't unpleasant. If I should decide to visit a gay bar in California, I think I'll have a lot easier time of it now.