Julie’s Weekend With (Mostly) Cis People

The planning for this weekend started with a cool event where my friend Gail was headlining at an amateur jazz night at a local restaurant/bar. It was a Saturday night a few weeks out and a number of my friends from the CD/trans community were planning to attend and show support. Of course, the first step for such an evening was to find a place to get my Julie on. Hotels, we’re looking expensive, cuz it’s summer in Chicago, so I started looking at AirBnBs. Found a place at a great price, just a block from Clark and Belmont. But, they required a two night stay. But, two nights there was cheaper than one night in a hotel, so I sent the owner a request with my usual explanation of me being a local and needing a place to transform into my alter ego Julie. After several message exchanges and talk about how it might not fit her work schedule, she denied my request. Damn! I’ll need to start from square one. But, thirty seconds later she messages again and says, send the request again and I’ll approve it. Now, I’m a bit leery and send a few more messages trying to gauge if she’s trustworthy. I resubmit the request and a few minutes later, we talk on the phone and both of us are a lot more confident about the reservation. I’ll talk a bit more about Janet, my host, a bit later. 

So, I have a room for two nights (Friday and Saturday) and activities for only one (Saturday). No problem, I’ll just get in early on Saturday and do some shopping. Later that day, I notice that there’s a burlesque show at the Newport Theater on Friday night — just a block from the AirBnB. I quickly message my burlesque friend, Jessica, to see if she wants join, and before I know it, we both have tickets for the 10 p.m. show. The next day, my friend Kurt posts on Facebook about the Frida Kahlo art exhibit happening at the College of Dupage, and within days we both have tickets for Saturday afternoon. Wow! That was quick. Okay, my schedule is now completely full — maybe a little too full. 

On the the Friday of that weekend, I had an online meeting all morning — which, of course, went long and I wasn’t able to get out of the office until 1:30. That gave me just enough time to get home, collect my son, so the two of us could walk to my daughter’s school, get all three of us in an Uber to the Metra station and put the two of them on the 4:10 train to grandma’s house — no driving to the burbs for Julie this time. Got home about 4:20, spent a few minutes tidying up the kitchen (gotta make sure I don’t leave the wife with a mess), grabbed my suitcase and took the CTA up to my favorite nail salon for a 5 o’clock appointment. Got to the salon a few minutes late, decided to go with white nails — cuz of the diversity of the planned outfits for the weekend — and made up a little time by skipping the hand massage. I had told Janet I would be arriving at 6 p.m. At 5:55, I’m under the fan, waiting for my nails to dry, and she texts me about how things are going. I say 6:15. A few more texts from her while in transit and I finally arrive at her place at 6:25. As you might be gathering, Janet is a bit eccentric. She meets me in the lobby of her building and the first thing she does is give me a big hug. That’s cool, I’m not naturally a hugger, but I love people who are. Actually, Julie is much more into hugging than the other guy, and since it’s a Julie weekend it fits very well. We talk about the key code to get in the building and head up to her apartment. It’s a fantastic space with all the amenities I could want and I immediately get to the business of getting my Julie on, cuz I gotta met Jessica at 8:30. I feel a little bad, because Janet wants to be a good host and make sure I have everything, and I’m like — l’m all good, I just need to get some makeup on my face. About a half hour later, Janet leaves for her dinner plans, which is a bit of a relief, but a little disappointing cuz she won’t see the final Julie. Of course, there was a mad dash at 8:15 with me being indecisive about the final details of my outfit, especially with regard to shoes — always the hardest decision. 

Get out the door and the air has cooled off from the midday heat, but it’s definitely more humid than I had hoped. I was meeting Jessica at a bar about a block from the Newport Theater. The Newport is close to Boystown, but officially in Wrigleyville. There was a Cubs game that afternoon, so that bar was packed. I walk in and the music is really loud — not great for conversation. Just as I’m finding a seat, I look out the window and see Jessica at an outside table waving her arms. Definitely a better place to talk, despite it being under the El tracks — gotta love the urban environment that is Chicago. 

I first met Jessica at my first burlesque performance. It was an event called Shoot the Shit, which was also at the Newport. Basically, for $20 they would make a video of your act, so you could publicize yourself. I’m not at the level where I need publicity, but I figured it would be cool to get a video just to see what I looked like. In any case, Jessica was there that night for the same reason and when I was on stage, she was the loudest one in the audience — everyone there that night was the audience for everyone else’s video. Somehow she found me on Facebook and a couple months later I happened to have a Julie night on a night she was performing at the California Clipper. After her performance, she found me at the bar and said she was so happy to see a friendly face in the audience. She, then, invited me to join her friends at a table near the stage. They welcomed me with no questions asked. Although, we have chatted a bit on Facebook since then, this was the first time I had seen her in person in about a year and a half (there was that little pandemic in the interim). It was great to talk in person as we chatted about the burlesque community, my recent visit to the Unbridled show at Untitled and just life in general. Here’s a little factoid that only Chicago people will appreciate. She works for a local tv station and actually knows Son of Svengoolie. At 9:30, we finish our drinks and walk over to the theater. As expected, the show was awesome — so much better than those online shows we had to resort to during the pandemic. The bartender is super friendly and I get a chance to talk a bit with Eva la Feva. She is also a performer, but more importantly, the theater manager at the Newport. During the pandemic, she put her heart and soul into keeping that place afloat and during the show I shouted out to the emcee for us to give a round of applause for Eva, which of course turned to a standing ovation. As expected, she was a little embarrassed, but it was so well deserved. After the show, the audience was invited to stick around and mingle. So, I stood up, looked around and noticed a woman sitting by herself. I introduced myself and waved Jessica over to join the table with my new friend, Heather. We talked for a while and then the three of us migrated to a bar which happened to be in the basement of the Newport theater building. Turns out, Heather is a burlesque veteran, so there was lots of gossip about the community. Jessica is only about a year ahead of me in the community, so there was lots of advice to go around. The disheartening thing about meeting Heather is that she is about to move to another state — great contact, but not great timing. However, the most important aspect of the evening was that somehow someone suggested that a burlesque show should be put together with the theme of Schoolhouse Rock — just crazy enough to be brilliant. As we’re leaving the basement bar, I remembered that I had yet to get a pic of my outfit — ya know, if there’s no pic, it didn’t happen. Luckily, one of them obliged and I got these great pics of me with the grittiness of Chicago at 1 a.m.

The next morning, I’m up before Janet (my AirBnB host), get a little Advil in me and pull out the breakfast I put in Janet’s fridge the night before. Shower, shave and get to work at painting my face. Time is of the essence. Here’s the plan for the day. We have tickets for the Frida Kahlo exhibit at 12:30. The museum is an hour from the city. Kurt is driving, but he lives on the South Side. So, I’m meeting Brent, Kurt’s ex boyfriend, at the Belmont train station at 11 a.m., so we can ride down to Chinatown and save Kurt a drive up to the North Side. Now, it’s gonna be really hot out in the burbs, so my outfit consists of a black tank top, a jeans skirt and cute flip flops with sparkly flowers.

I had expected to be exposing my toesies, so on the Thursday before, I painted them in my office — that day I had an 8 hour zoom meeting, so I had plenty of time to let them dry without anyone being the wiser. This was the first time Julie was wearing flip flops and the short walk to the train was actually a bit of challenge — boy mode Julie almost never wears flip flops. As usual, Brent gave a compliment on my outfit and a big hug. We’ve hung out several times before and now that I think about it, Brent and Kurt were my companions for Julie’s first time out in Chicago. This pic is the three of us eating outside at Wood in Boystown, back in 2017. 

With Brent and Kurt in 2017.

On the train, a couple of young women sitting across from us complimented me on my necklace. I told them I bought it at the MCA a few weeks before, which sparked a discussion about art museums. If I remember correctly, they were heading to the Art Institute to see the Monet exhibit. We shared that we were on our way to see Frida and we all agreed that the upcoming Obama portraits at the Art Institute were a must see. Kinda weird to bump into a couple of strangers on the train who happen to also be art lovers. Again, I just love living in Chicago. Kurt was right there as we got off the train and we embarked on what seemed like a forever drive. But it was good, because it gave all of us time to catch up after seeing very little of each other due to the pandemic.

Frida Kahlo’s art and a photo.

The exhibit was really incredible. Not any of the usual Frida paintings you see in pop culture. All were lesser known works that gave insight into who she was as a person. The one on the left was the most prominent of the exhibit. I was mesmerized by the eyes of her guard dog. The one on the bottom right was motivated by an article of a real life incident in Mexico, but many say it also portrays her emotional relationship with Diego Rivera. I’m actually more of a fan of his work rather than Frida’s — a print of his with giant flowers hangs in my office. Outside of the official exhibit, the museum put together a pictorial history of her life along with numerous artifacts. The photograph (top right) made me think that she was much more beautiful than she portrayed herself in her paintings — I guess trying to illustrate her inner turmoil. If you have ever seen the Frida movie with Salma Hayek, I have good news for you, it’s pretty accurate, historically. After the exhibit we hung out in the shady part of the courtyard and I convinced Brent to grab a few Julie pics — not the most flattering, but good for a historical record.

After a bite to eat at a local Mexican restaurant we started the trek home. I thought Kurt should have dropped us back at Chinatown,  but he insisted on driving us to the North Side. The traffic on Lake Shore Drive was insane and not any better when we got off at Belmont — weekend traffic in the city is no fun. After he dropped off Brent, I was like, no need to drive further into this chaos, just let me out here and I’ll walk the last few blocks — probably faster anyway, even with the flip flops. We parted ways promising to go see the Obama portraits, which given my current schedule, might need to be in boy mode, which is fine — he hasn’t seen me in boy mode in almost two years.

Back at the room, I quickly got to fixing up my makeup — mask at the museum combined with the heat had disrupted the makeup on my chin and upper lip. There was not much debate on what I was gonna wear — maroon dress with black patent strappy heels — another opportunity to show off my toesies. The plan was to take the Brown Line to Lincoln Square and meet Susan for dinner at a Thai restaurant before heading to the jazz show. However, before heading out, I got to thinking that those strappy heels are not all that stable and probably not ideal for walking to the train, especially if in a hurry. I had some flats I could have worn, but then I thought, why not go with my boy mode Converse Allstars? They worked out perfectly, as I felt like a typical city girl heading to the train in comfort and style. Waiting for the train a random girl complimented me on my dress, despite, or maybe even due to, the functional shoes.

Got to the restaurant and Susan and her wife were waiting for me. This was my first time meeting either of them. I’ve talked to Susan several times on Messenger, so it was great to finally meet her in person. Susan is the Secretary for the Chicago Gender Society, so our previous conversations have mostly been about raising awareness of the organization with younger folks — currently it’s membership is mostly older folks, which doesn’t bode well for the future of the group. However, on that night there was little talk of such things, as the three of us took the opportunity to get to know each other better. Of course, just after we ordered food, I dug into my new purse from DSW and changed into those decadent shoes. After dinner I went out for a cigarette and got my first real taste of walking around in those 4.25” babies. Yeah, definitely the right decision not to wear them on the train. 

It was a short drive to the Gail show, although we walked into the wrong place at first. The actual place is part bar, part restaurant. The small dance floor in the center of the place had been converted to a makeshift stage. We gave Gail a hello hug and left her to get prepared with the drummer and keyboardist who would be backing her up as we joined the others in our group. She looked a bit nervous, but once the show started — with a rendition of Life is a Cabaret — you would never know it. She’s not an incredible singer, but her stage presence made up for anything she might have lacked in that area. Between songs she told stories that were simultaneously touching and funny — a lot of self deprecating talk about who she is and putting our community in a good light. I should note that while our group was about a dozen or more, we didn’t make up even a quarter of the audience. After the show, she explained that during the pandemic she had joined this jazz singer group for zoom meetings, where they would take turns singing their favorite songs. So, most of the audience was people from that group. It was really a fun event, especially since it was a mix of the two groups. 

Please note the sign painted on the bar.

Things were breaking up about 9:30-10 and Susan and her wife were leaving. We said goodbye and I started thinking about getting an Uber to my final activity of the weekend. I was hesitant about asking them for a ride, and when I finally decided to ask, they were about a half a block away. So, there I was trying to catch up to them, almost running in those massive heels. They were, of course, happy to help, but a little concerned about dropping me off in what looked like a very desolate street at that time of night. The place was Reed’s Local, one of my favorite dive bars, in Avondale just a short distance from Gail’s show. I figured I would be stopping by there after the show, so a few days earlier I had contacted my friend Lauren, who is kind of a bar fly at Reed’s. Walking in, there was no sign of Lauren. No worries, there’s always someone interesting to talk to at a dive bar. But then, I stumbled upon Tina, who was sitting at the bar. Tina is part of the trans/CD community (actually uses the non-binary label) and I had contacted her a few weeks before to see if she wanted to go to Gail’s show. She said she was busy that night, which is why I was surprised to see her. Tina is the one who introduced me to Reed’s, so it wasn’t really that much of a surprise to see her cuz it’s one of her favorite haunts. We talked for a while and then I messaged Lauren, who said she was on her way — just finishing up with seeing her friend perform in a burlesque show. She arrived just as Tina was heading out — I’m not sure those two get along all that well. In any case, it was nice to catch up with Lauren outside of Facebook. She invited me to her birthday party, which I thought I might be able to make in boy mode, but, in the end, couldn’t make it work out. At some point, I was outside smoking and decided I had had enough of those shoes. But, before changing back to the Allstars, I asked a random girl to snap some pics. I think the best part of that pic is the sign painted on the front of the bar — words to live by ??

The next morning, I took my time packing up Julie into my suitcase and made plans to go out for brunch with my wife once I got home. On my final walk to the train, I noticed this little sketch on the sidewalk. Seemed like a fitting final expression of my great weekend.

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Tags: crossdressing, featured, Out & About

Category: crossdressing