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"I wanna love somebody
I hear you need somebody to love
Oh, I wanna love somebody
I hear you're looking for someone to love

'Cause you need to
Get back in the arms of a good friend
And I need to
Get back in the arms of a girlfriend"

Matthew Sweet’s album Girlfriend came out in 1991. I saw it listed in an end-of-year “best albums of 1991” article in the local paper (yes they existed then) and bought the CD (yes we did that then). It became one of my favorites, and if you haven’t heard it, I’d suggest using your favorite streaming service and give it a listen. More on this below. 

Friday September 23 was day two of my four day mini-trip. Day one, “Hail to the Orange” (published last Sun-Dee) included getting a pedicure and walking my former campus in Dee mode, then watching my Alma Mater win their football game in non-Dee mode.

I woke Friday morning to a loud noise outside my hotel room. My immediate thought was how rude to be doing construction early in the morning. Imagine my surprise when my watch said it was 9:16 AM, because I rarely sleep that late. I hadn’t set an alarm because I assumed I wouldn’t need it (I usually don’t sleep well in hotel rooms either).

My second thought was panic. My train from Champaign to Chicago was leaving in a hour and it takes Dee a LOT longer to get ready than non-Dee. I needed to do makeup and dress and drive to the train station. Time to get moving. I expedited my makeup and dressing and hustled out the door. 

My choice of outfits was the easiest to make; the same animal print dress I wore on my 2017 train trip to Chicago when I “trained pretty”, paired with my most comfortable boots. I made it to the train station in time, and parked outside. It took me a while to figure out how to pay for my parking (online), and then inside to the terminal, which was fairly crowded. I’ve been out enough that being in crowds doesn’t fase me anymore. However, when they announced that families and senior citizens could board first (I hit that target in June) I was happy to move towards the front of the line.

I found a seat next to the windows and settled in for the roughly two-and-a-half hour trip to Chicago. A young man–lots of college students headed to Chicago for the weekend–asked “Is this seat taken ma’am?” and he sat down after I said no. I passed the time on my tablet, one benefit of train travel.

We arrived in Chicago and after exiting the train my first order of business was finding a place for lunch. Because of my late start, I had missed breakfast, and I was hungry. It was about a mile walk from the train station to my hotel, easily doable. After a few blocks I realized walking in my boots, although stylish, wasn’t very friendly to my feet. I went into an office building–void of people save a security guard behind a desk–and dug into my suitcase for my new Blue Keds to wear the rest of the walk. Comfort over fashion–although I am sure the guard was wondering what I was doing.

I found a specialty sandwich shop–it used pretzels instead of bread–and placed my order. I had time to kill before my room was ready so I wasn’t in a hurry. I ate my lunch, played on my phone, took a few selfies (of course), and then eventually headed to my hotel.

My room was ready when I arrived so I checked in. As is standard these days, I provided my ID and credit card (guy me for both), but that has yet to be an issue. Again, I generally assume that people know I’m a guy in a dress, but I want to make sure it’s a pretty dress.

After checking in, I changed into a more casual of a white top with black stripes–a Hand-Dee-Down from my GG friend Michelle–and black jeans. As it was a cool afternoon–60’s and overcast–I also wore my fake leather jacket. I headed out to the Macy’s about a block away. At Macy’s there seemed to be a lot less inventory than my previous times in the store, an a lot fewer open changing rooms. I didn’t find anything that appealed, and headed out.

While looking for a place for an afternoon snack, I found an Akira store. I was introduced to Akira at the 2019 Pinkfest by former contributor Julie Slowinski. It’s a fun store, with similar vibes to Dangerfield stores in Australia. The store’s target demographic is also a bit younger and a bit hipper than yours truly, but I like to see if I can find some things that might suit me.

I found a few cute tops in the discount racks–a bit skimpy, but I continue to expand my comfort zones as to what I’ll wear–and with the help of an SA found a few things to try on. Skimpy or not, I liked the look, and was tempted by the look and price, but didn’t buy anything. It was approaching dinner time, so I stopped into a Panda Express and bought a carryout meal to have in my hotel room. 

After my dinner, I changed into a blue and gold Maggy London dress I had found at a thrift, but hadn’t worn it out yet. Blue is generally my color and Maggy London is my favorite brand, so buying it was an easy choice.

My evening destination was the musical Girlfriend at the Chicago Pride center.  The musical is a two man play about two gay teenagers coming of age in 1990’s Nebraska and incorporates several songs from the album (there was also a four person band to play the songs). It was a small theater–maybe 75 in the audience at the most–and I sat in the front row. It made for a nice evening.

I took the El to and from the show. Having been to Chicago many times, and having a sister who lived reasonably close to where the theater is located, I knew generally where I was going and felt safe taking the train. The only issue was a rider who sat opposite me on the way to the theater, chain smoking stubs of cigarettes (no, smoking is not allowed on the El) and singing in a loud voice. 

After returning to my hotel I redeemed the drink coupon I received at check-in for a nightcap at the downstairs bar. It was almost closing time, and the bar was mostly empty, but it was a nice finish to my day.


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