Fun Weekday in the City

Niki and Julie after a long day of fun.

About a week before the “Womanish” outing I attended a zoom meeting hosted by TG Detroit. My friend Niki happened to be there, so I said hi to her in the chat box. Turns out she was planning to be in Chicago the week after the Womanish weekend. After the zoom meeting, we talked some more on Messenger and settled on getting together on Thursday. After a string of weekend outings and all the family logistics involved with weekends, I was very excited about doing a weekday. In addition to fewer logistics family-wise, weekdays also mean cheaper hotels and less crowded venues. 

Of course, now that things were in motion, the detailed planning had to begin, which kinda overlapped with the planning of the Womanish evening. First was a hotel. About a block from my house, there’s a really cheap option, but I’ve always hesitated in the past because of the proximity to my boy life. Well, this time I decided to forget that nonsense and since it was so cheap, I would get it for Wednesday and Thursday. I wouldn’t actually use it Wednesday night, but the idea was to have it available early Thursday morning, so I could get my Julie on and be out the door by noon. I actually did check in Wednesday night and unpacked my suitcase a bit, so I would get a jump on the morning. That part was made a lot easier by being so close to home.

The next question was what to do with an entire day? We quickly settled on hitting a museum in the afternoon. Then, I suggested a jazz club in the evening. But then, a Chicago friend, Luke, posted about going to see the Unbridled burlesque show at the Untitled Supper Club. So, I immediately jumped on board with that, ditching the jazz club idea even before checking with Niki. I’ve been wanting to see that particular burlesque show for a couple of years now, and this was the perfect opportunity. Those were the broad strokes of the day, but let’s get into the play-by-play, cuz there were so many other impromptu activities with this long day. 

Niki arrived at the hotel about 11:30. I got our tickets for the Museum of Modern Art for 2 p.m., which gave us time to grab some lunch beforehand. Waiting for the Uber in front of the hotel, a couple odd things happened. First, a trans woman walked past us and before going inside, made a point of saying, hi ladies. Now, Chicago has plenty of trans folks, but that’s the first time that’s happened to me. Her friend, I think also trans, was waiting in the car and when the first came back out, she did a little dance at the car door finishing with a reach for the sky, before she got in and they drove off. Niki and I looked at each other and I was like, ya don’t see every day. At some point, a guy (possibly non-binary, possibly bi, definitely not cishet) walked past and said hi to me. Our Uber was taking a while to arrive, so it was not surprising for him to walk past a second time, again giving me a look that I acknowledged with another hello. But, then he walked past a third time, which seemed a bit odd and I tried to make a conscious effort to ignore him. So, the day was already off to an interesting start. 

Lunch was planned for a Thai restaurant near the museum. But, for some reason they were closed for lunch that day. No worries, there was a sushi place right next door. I’ve actually been to that particular sushi place, in Julie mode a couple times before, so I knew it would not disappoint. Plus, Julie never turns down sushi. Luckily, Niki was okay with the sushi option, which is not a given for everyone. I have to say that Niki is so awesome. Not everything we did was in her usual set of activities, but she is so easy going that nothing was ever an issue. Again, not a given for everyone. The museum was great, although being a modern art museum, we didn’t understand all of the exhibits — par for the course at the MCA. However, the art in the pic struck a chord with both of us and we made a special trip back to it to get pics with it. We’ll talk about my outfit in a minute, especially those shoes.

After the museum we did something really special. I haven’t discussed this before, but I’ve been getting laser treatments on my facial hair since about February. At 50, my beard is about half black/half grey. So, the idea is that the laser will eliminate only the black and thin things out to about the level that I’m looking for. Most people will just think that I’ve just gone fully grey. In any case, the laser place is in the Water Tower Place mall, right next to the museum. I always go in boy mode and happened to have a treatment two days before. So, when I was there, I asked if I could stop by on Thursday just to say hi in Julie mode. They were like, sure, no problem. Now, I’ve done similar things before. For example, after getting my nails done in boy mode at some random place, I’ll go back after getting all Julie’d up and sometimes it’s a bit awkward. Luckily, there was no awkwardness this time. They were really excited to meet Julie. We actually talked for quite a while. They were interested in our plans for the rest of the day and of course we talked about how the Macy’s in the mail had closed and how we all miss it. At the end we all got a picture together, but with their iPad and I forgot to ask for a copy. 

After that fun visit, definitely a lot more fun than the laser treatments, we stopped at the White House Black Market in the mall — one of my favorite stores. We didn’t buy anything, but the sales associates were super friendly and we chatted them up for a good 15-20 minutes. Of course, there were complements all around on everyone’s outfit. Okay, let’s talk about my outfit. Back at the museum, a janitor lady stopped what she was doing, just to talk to me about my cute pink Mary Jane heels. I guess that’s not too unusual. At the WHBM there was another discussion about my shoes — maybe even a compliment on how the colors of the whole outfit coordinated really well. Then, on the way out of the mall, Niki overheard some random woman talking to her friend about my shoes and how cute they were. Needless to say, I was on cloud nine from all those complements. My confidence was through the roof. At that moment, I specifically remember feeling great, keeping my steps small, shoulders back and making the most of feeling dainty and pretty. 

At this point, we had a few hours before we needed to get back to the hotel to get changed for the evening. So, I gave Niki a few choices: 1) go to Bloomingdale’s across Michigan Avenue and try on pretty dresses, 2) go to Neiman Marc?s, same distance in the other direction, which I have never been to, 3) get an afternoon drink at the rooftop bar at the Ritz Carlton hotel, which we were standing right in front of. Yeah, I know — how can you go wrong with those 3 choices. Niki was ready for a drink, so in we went with the doorman holding the door open for us. The rooftop is only on the 6th floor, but it’s right next to the 98 story John Hancock Building and has a great view of the other buildings in the area. As we were walking to our table, I noticed a smartly dressed woman with a martini glass that had cucumbers lining the rim. After a short talk with the waitress, Niki and I both had one of those refreshing drinks in front of us. It was such a nice atmosphere on a beautiful May afternoon and we had a great conversation about all sorts of topics — ranging from kids to TERFS. The waitress wanted us to get a second drink and we were tempted, but we were like, we’ve got some activities in the evening and need to pace ourselves. It’s a good thing, cuz when the bill came, we found out that those drinks were like $17 each — nice to visit the Ritz Carlton, but don’t stay too long.

We still had some time, so we decided to make a quick stop at Neiman Marc?s. Wow! We didn’t even dare try anything on. I saw a dress I really liked, but at $2700, I was afraid touch it much less try it on. The shoe department was fun. Nothing under $250 and I would have tried on some of them, if anything had struck a cord with me. It didn’t really matter, cuz it looked like the largest size they had was 42 (of course, they were all European sizes), which is about a 10.5 — I’m an 11. By far, the best part of NM was the bathroom, which had a full length mirror and great lighting — perfect for some quick mirror selfies.

At this point, time was getting short and we needed to get going. I got on my phone and looked for an Uber. It was almost 5 p.m. and the traffic was looking crazy, confirmed by the 35 dollars Uber was quoting for the short trip back to the hotel. That, along with how long it took for the Uber to show up that morning, encouraged us to make the three block walk over to the train. I’m not sure if that was Niki’s first time on the train, but as usual it was uneventful and definitely the right decision. As we walked, I joked with Niki, “At least it’ll give more people the opportunity to see my fabulous shoes” 

Back at the hotel, I quickly got to work updating my makeup for the evening — darken up the eyes, add some big lashes and red lips to go with the planned red dress. I got that dress from Nordstrom, about six months earlier, and have been waiting for the right opportunity to wear it. If you remember, I had tried the week before, but the weather wasn’t cooperating. This night, the weather was warm and it was the perfect amount of dressy for Untitled. Before, heading out the door, I grabbed a quick mirror selfie. [mirror selfie in red dress here]

We got there at 7:35 and Luke was waiting for us at the table. How do I describe Luke? I met him through the burlesque community on Facebook. He’s thought about performing, but is more of a superfan. He’s actually doing a PhD in history, and in the process of writing his dissertation on the history of burlesque in Chicago — such important work. It was my first time meeting him in person and the three of us had a great conversation. Interestingly, I had to explain that I’m not full-time, which from my Facebook page, might not be entirely clear for cis people. The show was, of course, awesome. The host was a drag king, I kinda know from Facebook (we’ve never actually talked) and there were four performers each doing two routines. They were all great but the last, a woman with the stage name Ammunition, was the highlight of the night. She is another Facebook friend and her act involves a metal grinder with sparks flying in all directions.

Ammunition at work.

As we were heading out, we stopped back at the reception desk to chat with those wonderful people. I remembered a couple of them, and was surprised that they remembered me from the last time I was there to see a Blues band — I guess Julie is a bit memorable. In any case, we convinced one of them to get a few pictures of the three of us.

Luke with the ladies.

 After we said goodbye to Luke, Niki and I decided to head over to the Jazz club of the original plan — just a few blocks from the hotel. It was a beautiful night, so we decided to again skip the Uber and make the short walk across the river to the train. The river at night is the best for getting a great view of the city lights — I’ll never get tired of that view and I think Niki really enjoyed it. We didn’t have tickets for the Jazz club, but being a 10 p.m. show on a Thursday night it was no problem to just pay the cover at the door. The only issue I have with most jazz clubs is that they’re not so conducive for talking — the other patrons kinda frown on it. It’s kinda like talking during a movie. We were in the mood for talking, so we sat way in the back by the bar and did our best to keep our voices low. Of course, we got one last pic of night, compliments of our friendly bartender.

And that was it. We made the short walk back to the hotel, deconstructed and I made the short walk home — kinda nice not having to lug that Julie filled suitcase on the train, like I usually do. A perfect ending to a perfect day.

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Tags: crossdressing, featured, Out & About

Category: crossdressing