Sweet Home Chicago: “Part VI – My Kind of Town”


I wonder if my family ever thought me insane as I was preparing to leave the the School of Hard Knocks aka Queens NY, for the friendly confines of the Windy City, to visit a girl I had met on line. Maybe they didn’t think I was crazy at all. Perhaps they were glad that I was showing interest in something other than music, comic books, and movies. They might have even gone as far as thinking that my little crush on Jess was down right adorable. I’m not sure what they thought at the time. I’ve never bothered to asked them about it either; and I was so self absorbed with this newfound love of mine that I wouldn’t had notice if the world had blown up around me. However I am pretty certain that they never thought that my relationship with Jess was going to be a long term thing. How could it? No matter how close we were in spirit, our bodies were still separated by what must have seen to them as an insurmountable distance. But none of that mattered to me. I was beyond infatuated with Jess. She had lit something within me. Something that was not tangible. I couldn’t place my finger on it. It was driving me. And it was advising me to “GO WEST YOUNG MAN!” So west I went.

My father was kind enough to accompany me to Penn Station on the day I was leaving for Chicago for the first time. It’s funny, but I can’t remember if he passed on any words of wisdom or any quick one liners that might impress the misses while we waited at the station for the boarding call to be made. I’m sure he did, since the man always did love to talk. But I can’t recall anything that may have stuck out. Then again I am pretty surprised I recall anything considering how excited I was. The only thing going through my mind was OH MY GOD, OH MY GOD, OH MY GOD!

My father was kind enough to hook a brotha’ up with a box of condoms, $300 of spending money, and my round trip Amtrak tickets that cost an additional $66. That was an insane amount of money for that man. He was living a pretty hard existence, and I am sure that he virtually gave me every last cent he had to his name in order to make that trip happen for me. But he thought that it was totally worth it. He was seeing me off as a proud father. In his eyes I was going of on a noble quest. And when I returned, I would be coming back as a conquering hero, and a chip off the old block. He must have thought that once I returned we would finally establish our relationship, all wounds would be healed, and we would be a family again. It sad that things didn’t turn out that way for us. This would be the closest my father and I would get to being best friends again.

The only thing I remember my father saying to me before I went off to board the Lake Shore Limited to Chicago, was that he was extremely proud of me, to be very careful, and to “Make sure you enjoy yourself heartbreaker”. I was planning on it. I thanked him for everything. I hugged him. I grabbed my roll on suitcase, my book bag that was carrying a couple graphic novels and my trusty CD player, and boarded the train.

I was about to embark on a 23 hour trip. I had nothing to do but sit on my ass and think. The whole thing seemed so surreal to me. What the fuck was I doing? I started to grow anxious about what I was getting myself into. I hadn’t traveled outside the borders of NYC in almost a decade. Besides Jess I didn’t know anyone in Chicago. I was not familiar with the city. I didn’t know what she had planned, if anything. And worse yet, what if Jess took one look at me and suddenly got a case of cold feet? What if she found me unattractive, unappealing, brash, awkward, fat, ugly, stupid? What if she just outright rejected me? Then what? What the fuck was I going to do? How could I face my family if she did? I didn’t know if I could go through with it. But it was a bit to late to turn back. I tried to push back those thoughts deep into the darkest deepest corners of my mind. But I could hear their echo. I was sure I was setting myself up for a disaster. I loaded Radiohead’s O.K. Computer on the CD player, and quietly watched the world pass.


If my memory does not betray me, the Lake Shore Limited arrived to Chicago Union Station on September 18, 2002, sometime between 11am and 2pm Central Standard time. My train had arrived about 2 hours late. I was tired, sleep deprived, cramped, and was very anxious to get off the train after being encased in a glorified tin-can for almost an entire day. A feeling of great relief came over me as they opened the doors. I grabbed my gear and wobbled my way off the train. My legs and back were as stiff as a board. I hadn’t showered in over a day and I was feeling a little self conscious about it. I was thankful that I had worn my favorite, non wrinkling, blue, Ecco, button down short sleeve shirt. or I would have looked a bigger mess than what I was already feeling. I walked off the platform with my few belongings and dragged my self over to the Union Station Waiting hall where Jess had told me she would be waiting for me.

I remember walking into the cavernous hall and being impressed by the look of the place. The hall had this tall arched ceiling with a skylight which bathed the entire hall with natural light. It reminded me of a smaller yet brighter Grand Central Station. I remember there being several large pillars by almost every doorway and entrance in the hall. I’m not a big architecture guy, but I will say I was digging the design quite a bit. The other thing that stuck out was how clean the whole place was. The entire place had a pristine look, as if I had traveled back in time to when the station had first opened back in 1925. I was also surprised by how deserted the whole place seemed to me. I looked up Union Station on Wikipedia cause I was a bit curious on the history of the place. And it mentions that the station is the “3rd busiest rail terminal in the United States, handling 120,000 passengers on a weekday.” But as whatever deity you prefer as my witness, I swear, I recall asking myself where was everybody. I remember there only being a few stragglers here and there. There must have been thousands of people still waiting around at Penn Station when I had left the day before. Yet here I was standing at what I thought was the main train terminal for the third largest city in the country and it was virtually deserted. Thankfully the lack of people walking about made it fairly easy for me to spot Jess; who was sitting at the far end of one of the benches across the Waiting Hall.

I was anxious. Very, very, anxious. I wasn’t breaking out on cold sweats or anything. But I could feel my heart beating in my chest as if it was trying to bust through my rib cage and hop out before it got ripped out. I made a mental note to get my shit together. I willed my legs to move forward. Jess was sitting on the bench quietly. She was staring down at her cell phone the whole time. I don’t know if she was texting someone who was advising her to keep her rape whistle handy in case anything got out of hand, or if she was just playing some mini game. Whatever it was that she was doing with that phone, sure had her undivided attention, because not once did she ever bothered to look around to see if I was in the room. This gave me the impress that she was just as nervous as I was. That revelation allowed me to feel a bit more at ease.

Jess was wearing basically the same style of attire she wore in the first pic I had ever seen of her. A blue colored short sleeve T-shirt, with another gray long sleeve T worn underneath. She had a pair of form fitting blue denim jeans on, accompanied by a wallet key chain that hung on the side. She had passed on wearing her face stomping boots for a pair of comfy sneakers. Probably to aid in her escape if she had to sprint away from me at a moments notice. Clever girl. And just like in her picture she wore her hair in a tight bun, but with her black curly hair parted straight down the middle. Despite the grungy attire, it was immediately clear to me that she was even more beautiful in person than in any picture that she had ever taken.

It was time for the moment of truth. I made my final approach. I dug deep down into my gut to bring up as much base in my voice as my 400 plus frame could muster, and simply said, “Hey Beautiful.”She looked up at me. Our eyes locked. What would her eyes tell me? Was she happy? Was she relieved? Would she still approve of me? Was I too unattractive? Would they be filled with regret? It was at that moment that she flashed on of the more beautiful smiles that anyone had ever beamed in my direction. She was happy. Genuinely, unapologetically happy to see me. She got up, and we hugged. I didn’t think it was good idea to use that moment to shove my tongue down her throat. After all I had just won my first major victory. I didn’t feel the need to push it. Why run the risk of seeing her go fleeing in to the hills screaming “KILL IT! KILL IT!” The hug would suffice. After the hug she quipped that it was about time I had gotten there. She had been waiting around for two hours 2 hours, because my train had been delayed. Once again the woman was busting my balls. God bless her wicked little heart.


I was exhausted from the long journey and was feeling a little unkempt; I had asked Jess if she minded if I could check into the my motel and possibly take a shower. She happily obliged. I loaded my bags in the back of her sisters CRV, which she had borrowed to pick me up, and we made our way to the town of Willowbrook where the Red Roof Inn I was staying at was located. During the drive we filled the time with the usual senseless small talk that fills conversations when you clearly like someone but don’t want to say anything that might make you come off as a complete idiot. I wouldn’t say that we were tense around each other, but we were being a little guarded.

Jess took the scenic route. I got a clear view of the gorgeous Chicago Skyline. The hustle and bustle of the down town area. The tree lined streets. The ocean like vastness of Lake Michigan. The climate was warm but with a cool breeze that made it nearly impossible to break into a sweat unless you had a grand piano strapped to your back. Chicago reminded me a bit of New York, but with a smaller less chaotic skyline, no syringe polluted waters, and no stab victims being loaded into the back of an ambulance ever dozen blocks or so. It looked like heaven. I complimented Jess on the look and feel of her home town. She joked that she had done her best to fix up the place to make it look good for me. I laughed.

We pulled up into the Red Roof in about 1 hour later. We had spent the whole time growing more comfortable in each others presence. Smiles where being flashed left and right and we had even held hands for part of the way. I was about to start making my move to open the door so I could go to the check-in office, but before I pulled open the handle, I turned back and politely asked “You mind if I give you a little kiss before I go in.” She smiled at me and shyly said yes. So I leaned over and gave her a small little kiss on the lips. We both smiled. I made the move if I was going to open the door for real this time, but I turned to her again and said “O.K. Maybe one more for good measure.” She smiled again and leaned in and kissed me once again. This time with a bit more feeling. I was all smiles. I’ll be back I told her, and I made my way to the office. For the first time I allowed myself to think that this just might workout after all. It was going to be an awesome 5 days.

To be Continued: Sweet Home Chicago Part VII – Only in Dreams

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