“Memento” Day in Chicago

In contrast to other of my solo outings, this one (January 7, 2020) was pretty much planned, cuz I had a lot to accomplish and any partner in crime probably wouldn’t appreciate the packed schedule nor the multitude of Uber rides. To make this story a bit more interesting, I’m gonna describe the day in the style of the ‘90s movie Memento…

– 2 a.m. back at the hotel. Seems like I’ve been wearing this makeup for 11 hours, but don’t remember doing any touch ups. That setting spray must be doing its job. Time to deconstruct and get home.

Bar mirror selfie.

– 1 a.m. at a Boystown bar called Bobby Love. I’m kinda drunk and probably didn’t need this last drink. But, I remember my bartender friend Adam moved here from Cell Block, which is the bar across the street (see the sparkly dress pic below, which was taken by Adam outside of Cell Block, the first night I met him about 2 years ago). The evening bartender informs me that Adam is working the day shift. I guess that’s probably a good thing for his social life and probably good for me, cuz I’ll be doing less chatting and head home soon. But, before doing so, I get this cute pic of myself in the mirror behind the bar.

The sparkly dress.

– 11:30 p.m. at the Hungry Brain. Enjoying some late night, free form, jazz played exclusively by audience members — a Tuesday night tradition at this Avondale bar. I’m probably the only non-musician in the place and definitely the only one in a skirt and heels. As I strut in like I own the place, I get a few looks like, “what’s this over dressed person doing here?” but everyone is too interested in the music to pay me much mind. As usual, I totally enjoy the two sets I’m able to catch.

– 9:10 p.m. I arrive at the California Clipper in Humboldt Park for their first Tuesday of the month Burlesque show. My Facebook friend Eva La Feva produces this show that I’ve been wanting to catch for a couple months now. As an added bonus, my new friend Jessica is performing professionally for the first time tonight. We met at my first amateur Burlesque performance (at the Newport Theater, where Eva is also the theater manager). That night, Jessica was the loudest one in the audience while I was on stage, and I was pleasantly surprised to find a Facebook friend request from her a couple weeks later. She was the first performer this particular evening and afterwards, came to find me in the audience — saying that she was so happy to see my face while she was on stage. Then, she invited me to join her and her friends at one of the tables up near the stage. They were all cis (as is Jessica), but not a one of them batted an eye as I was introduced and I said hi in my deep, distinctly male voice. So awesome to meet and hang out with nice and totally accepting people. Unfortunately, I didn’t get any pics at the Clipper. 

– 7:30 p.m. I arrive at Hamburger Mary’s in Andersonville for their “Let’s Make a Diva” night. Basically, this is their amateur drag night, which is every Tuesday — eight contestants enter and the top two, by audience selection, move on to the next round. I’m particularly interested in this show, because at some point I’d like to be one of the contestants — actually the original objective of taking those Burlesque classes. So, I grab a seat at the end of the bar and wait for the show to start. However, I quickly realize that if I move over a few seats, I’ll get a view of myself in the mirror behind the bar. The problem with that move is that it puts me a couple of seats away from this guy drinking tallboy beers by himself. Within 2 minutes he taps me on the shoulder, my back is to him because I’m angled toward the stage. I turn and he raises his beer and I raise my vodka cranberry, to be polite, and we have an awkward cheers. He keeps trying to pull me into conversation and I oblige, but it’s again mostly awkward. I should note that I’m very open to conversation with strangers, especially sitting at a bar. But, he’s having a really hard time keeping my attention, because I’m preoccupied with getting a feel for how this amateur night works. Then, after telling me how beautiful I am, he just comes out with it and asks if I date. I’m like, “sorry I’m married” and show him the guy wedding ring on my finger. Ten minutes later he asks if I was single, and I look at him like, “I just told you I’m married.” So, now I’m doing my best to just ignore him and watch the show. Well, I guess he figured I was slipping through his fingers and decides to get up and stand between me and the stage. He insists on buying me a drink and I’m dumbfounded by his desperate tactics. I tell him that I’m actually about to head out, but would like to see this last act. He’s crushed and thinks I’m leaving because of his obvious rudeness. He’s actually lucky that I had a Burlesque show to get to, otherwise I would have had the bartender throw him out, or worse have the MC give him a public humiliation. In any case, it’s enough for me to start looking for the bartender for him to back down and return to his seat. When I think back, there were like 30-40 queer folks in the place, most of them very friendly looking lesbians, and I decided to set next to the one chaser in the place — all because of my vanity and that stupid mirror. I should note that at no point did this guy think I was a cis woman. In the end, I got to see enough of the show to figure out that most of their performance is not on the stage, but out among the audience. This is not what I expected, cuz I figured it would be more of a stage performance. So, I now know what kind of routine I should be trying to put together. Actually, this is very useful information in my current burlesque class, where we are focusing on connecting with the audience — exactly the mindset I need for being up close and personal with the audience.

– 6:15 p.m. Just arriving back at the hotel for an outfit change The black tights and suede ankle boots were perfect for a daytime look, but I’m thinking about something a bit sexier for the evening. Also, those boots were hurting my toes because I did too much walking and didn’t have thick enough socks. In the room, I change out of the tights and into hose that are more shear but still a dark black. I try on three dresses as well as several shoe options, including knee high boots. In the end, I decided to go with the same top and skirt and other than the hose, the only major change is into my suede round toe heels. I also opt for a clutch purse and a more dramatic necklace, an orphan Christmas gift that I gladly gave a home without anyone but my wife noticing. 

– 5 p.m. I make a stop at the Virgin Hotel in the Loop for a quick drink and maybe an appetizer. Of course, I order a Cosmopolitan, which is always my first drink of the night on a Julie night out and also fully enjoying a cheese board that included sourdough toast and a yummy honeycomb. The hotel bar wasn’t empty, but definitely not anywhere close to crowded, so I didn’t really talk to anyone other than the bartender.

On the way out, I stopped at the ladies room and noticed a nice mirror and got a pic with my fabulous coat . By the way, I have a similar guy coat that Julie has warn in the past. This new coat, while not as warm, has much more of a feminine cut around the waist, which is why I like it so much more. After waiving goodbye to the very accepting hotel concierge who had directed me to the hotel bar, I head to the CTA. Unfortunately, I had forgotten to transfer my train pass from my guy wallet to my Julie wallet. I had thought about getting an Uber, but at that time of day the traffic was probably gonna be a nightmare. So, I just bought a new pass for $5 — figuring that my son has lost enough train passes that I’ll be giving it to him eventually. On the train, which was totally packed, I felt totally at ease — I was dressed completely appropriate for a professional woman heading home from a day at the office and even though no one who noticed me thought I was cis, the percentage of people not completely engrossed in their phone was minimal. After I got off the train and before getting on the bus, which would drop me directly in front of the hotel, I made a quick stop at Lovers Lane. A few weeks earlier, I was in there, in boy mode, looking for a corset for my burlesque costume. I felt kinda bad because I had tried on 5 corsets and didn’t buy anything. The sales associates were super nice and didn’t mind at all that I didn’t find anything I liked. So, I was hoping to find the same associates, mostly to show them what Julie looks like and also to show a pic of what I did find for the show. One of them was there, totally remembered me and was really excited to met Julie as well as see the pics of the pink corset I had found. The bus ride was for the most part uneventful, but much warmer than walking. 

Julie with the Marsha P. Johnson Warhol painting.

– 3:30 p.m. arrived at the Art Institute to see the Andy Warhol exhibit. A few weeks after the opening of the exhibit, Julie went to a members only lecture about Warhol and planned to see the art afterwards. Don’t know what I was thinking, but I should have expected that the exhibit would be packed after the lecture. So, I decided to leave and come back another time. The exhibit ended at the end of January, so this was probably my last chance to see it in Julie mode, I could easily find time in boy mode, but what fun is that? The Uber dropped me off in front of the Michigan Avenue entrance, but I decided to walk over to the north entrance, by the modern wing. I figured I could sneak in a cigarette, but also allow me to strut a couple blocks in my fabulous coat and suede ankle boots — totally worth the the little detour. To be honest, the exhibit was a bit of a letdown. I’m sure the problem was that about a year before, Julie had visited the Warhol museum in Pittsburgh — spent 4 hours absorbing as much as I could. While this exhibit had lots of good stuff, it just couldn’t compare to a six story building devoted almost entirely to the man. The saving grace of the visit was that I got a picture of Marsha P. Johnson (the drag queen most people attribute to throwing the first brick during the Stonewall Riots). I had gotten a pic of her in Pittsburgh, but didn’t have the presence of mind to include myself. After the museum, I thought I would grab a drink at Cindy’s rooftop bar, just a block away and with a magnificent view of the city and Grant Park. But, when I got there, the doorman informed me that Cindy’s was closed for renovation, which was their state the last time I tried to visit, after going to the orchestra about a year ago. As an alternative, I decided to make the 6 block walk to the Virgin Hotel for an early afternoon drink.

– 1:30 p.m. Checking into my hotel, in boy mode, in East Lakeview. As usual, the girl checking me in, complements me on my nails — in the pics you might have noticed that deep, dark purple I had selected for the evening. It usually takes me 2-2.5 hours to get my Julie on, but I’m planning to go to the Art Institute — which closes at 5 p.mm — so I need to figure out how to cut that prep time as much as possible. I’m diligent and am ready and out the door by 3:10 — I’m rather impressed with myself, especially since I didn’t really know what I was gonna wear before I got started. Maybe the key was to skip the false lashes, which are always trouble.

– 12.30 p.m. I arrive at my favorite nail salon. While my friend Natt works on my nails, we chat about my recent burlesque performances and my Facebook post entitled “2019 a Year in Review via Nail Color”. Since she did about half of those manicures she very much appreciated seeing the post. For the first time, I have to admit to her that I’m totally up in the air about what I’m gonna wear that evening.

– 10 a.m. At home. Been furiously trying on outfits, without hip pads, to see if anything is feeling right. Not really feeling it, so I head back to the closet to see if there is anything I missed. Pull out a few tops and skirts and hold them up in front of the mirror. Black top and grey skirt looks good, but no time to try it on, cuz I gotta get in the shower and shave my face if I’m gonna have time for the nail solon and get my Julie on early enough to make it to the Art Institute. I’ll just have to figure it out at the hotel.

– 8:30 a.m. At home. Kids and wife finally out the door. Got a long day planned, but I’m kinda tired from a busy Monday — maybe a quick one hour nap before getting moving on my ‘day off.’

Wow!!! What a day – I should go solo more often.

Like to make a comment? Login here and use the comment area below.

Tags: crossdressing, featured, nightlife, Out & About

Category: Out & About