Drive-in Drag!

At the Drive-in Drag Show.

Well, the pandemic is still taking its toll. While I’ve been out once since the start (maybe you remember my Drag March for Change story), most of my friends haven’t found the right opportunity. We’ve tried to make plans, but the activities we usually do (restaurants, live shows and dance clubs) are either not open or don’t really feel safe yet. This is on top of our usual problem of trying to get our family schedules to align. 

But then, I noticed a Facebook ad for a drag show. Not the usual “in a packed dance club” drag show, but a socially distanced show modeled after a Drive-in movie theater. And not way out in some far flung suburb, but in downtown Chicago; the Soldier Field parking lot — go Bears. So, I quickly texted Claudia, cuz she loves drag shows and has been desperate to get out. She was immediately in. My other bestie, Jessica, took a little longer to decide, but we eventually convinced her that we could minimize the risk — she’s about 10 years older than me and is rightly concerned about Covid. We would have had our usual powerhouse foursome, but Danielle, the young’en of the group, had to work that Saturday night. 

So, I worked out the family details with my wife and we were officially on for a Julie night. In fact, the schedule allowed for me to make it into a two night in town ‘trip’, Friday and Saturday night. 

At this point the only problem left was to figure out what to wear — not at all a bad problem to have. The one snag was that I usually have some time at home to try on outfits and figure out what’s feeling ‘right’ and coordinate accessories. But, with the kids around, pretty much 24/7, I had to do a lot of mental visualization. The net result was that I packed way too much — just so I could have ‘options’. Of course, Claudia and Jes thought the massive pile of shoes and packed hotel room drawers pretty funny. 

Friday morning finally came and the first task was to drive the kids to grandma’s house out in the burbs. The problem is that with the lax Covid schedule, those kids don’t get out of bed until about 10:30. A couple days earlier, this was a good thing, cuz I could pack my overstuffed suitcase in the morning without concern that they might walk in and I would have to explain the hip pads in my hand. But, on the big day, it was a struggle to get them in the car so I could get back and head to the hotel at a reasonably early enough hour to do something with the evening. 

I managed to get the hotel around 2:30 and immediately started on my makeup. OMG, I’m so out of practice and the makeup process took way longer than expected. And then, I still had the outfit coordination issues to figure out. After lots of hemming and hawing, I was just about to walk out the door in the pic of the red top and black skirt pic outfit. But, at the last second, I changed to nude heels and a tan over-the-shoulder purse. The colors kinda worked and I was able to fit emergency flats in the smaller purse.

I had a nail appointment at 6:00 p.m. at a salon in Boystown, about a block and a half away. I immediately regretted the heels, not so much for the walk, but because they were just out of place for 6:00 p.m. on a warm Friday afternoon. I then realize that my triumph of getting the flats in the purse was pointless, cuz if I changed, the heels wouldn’t fit. Normally, I would get my nails done before before going to the hotel. This is because experience tells me that being at the salon is always more comfortable in boy mode. But, since it had been a while since I’d been out, I thought I would try to maximize my Julie time. While getting my nails done in the Covid mask and feeling kinda over heated from the walk in the hot sun and thinking about how my makeup was getting smeared under the mask, I thought, “Okay, maybe stick to my usual routine next time.” 

The original plan for after the salon, was to hang around Boystown for a bit, maybe get a drink and then catch an Uber to meet my friend Tina for dinner at eight. But, I just wasn’t feeling all that comfortable being overdressed. In addition, Boystown was actually a little too busy for my liking — not enough people were wearing masks. So, I decided to walked back to the room. After a short distance I did pull out my sparkly flats from my purse. The heels kinda fit in the purse, but were sticking out, which was fine for the short walk back to the hotel — I was immensely more comfortable, both physically and emotionally, in the flats.

At the hotel, I switched back to my black purse and headed to the restaurant a bit early. I figured it would be fine to be early, cuz I had a Martha Graham Cracker show I could watch online while I waited for Tina to arrive. If you don’t know who MGC is, you need to do some Googling, cuz she’s so awesome and talented.

The restaurant was this great little tapas place in Logan Square, called Azucar. They have awesome food, outdoor seating and the owner is super chill and friendly. We ate and talked and drank and eventually went over to Tina’s place to sit on the porch and talk and drink to the wee hours of the night. It was my first time at her house and it was great to see all of the eclectic hobbies she’s into as well as meet her super friendly cat. 

The next morning, I was a little slow getting up, but needed to get rolling if I was gonna make it to my appointment at the art museum. So, I found a breakfast diner down the block from the hotel and ate some bacon and eggs in boy mode, but with pretty nails, which no one much noticed or cared to notice in this Lakeview neighborhood. Got back to the room, hopped in the shower and got going on my makeup. Since I would be day-walking, I tried not to go overboard with the makeup. Not sure I succeeded, but I definitely cut the time in half and was out the door by noon — a full two hours before I was scheduled to meet my friend Kurt at the Museum of Contemporary Art (see the black skirt pics for my afternoon outfit). I was especially pleased with how well the kitten heels worked out — nicer looking than flats, but not so out of place as regular heels on a Saturday afternoon. And surprisingly, they didn’t seem to make my size 11 feet look all that big — still trying to figure out why. 

At Macy’s.

Arriving early, meant that I had time for some Mag Mile shopping (see the Macy’s shoe department pic). At the museum, it was nice seeing the art again and catching up with Kurt — we haven’t seen each other since before the pandemic. But, my mind kept wandering back to the ‘on sale’ heels I had passed on, back at Macy’s. Needless to say, when I finally got back to the room, the second thing I did, after giving Claudia a big hug, was show off my new heels. It was about 5 o’clock and since Claudia was still working on makeup and Jes had yet to arrived, I decided to take off my wig and grab a quick cat nap. Once they were close to ready, I quickly touched up my makeup, red lipstick this time (to match my nails), and changed into a sparkly skirt and the nude heels I had ditched the night before — looking totally fabulous IMHO. Not sure why I didn’t get a pic at that point, probably just anxious to start the evening. 

We had dinner at this Asian place called Ping Pong — just a block from the hotel on Broadway. We had been there before, but it was maybe a year and a half ago. So, we were surprised when the hostess remembered us and welcomed us like regulars. Of course, we got outdoor seating and the food was as expected — fabulous. I got the fish and Jes was like, I can’t remember when you didn’t get the fish. Jes is one of the first CDs I had met in person, so we go back quite a while. I guess the point being that this seemingly innocuous comment just reminded me of how long we have known each other and how much I missed her.

After dinner, we stopped back in the room to freshen up before the 9:30 drive-in show. They both needed cash (to pay me for the tickets to the show) and we needed some alcohol for the show and for hanging out in the hotel courtyard afterwards. So, we decided to stop at a nearby supermarket to do both. Claudia is a little shy about being outside of LGBT spaces, so later in the evening she confided that that was her first time in a supermarket as Claudia. It’s actually quite amazing to me that I’ve gotten to the point where I don’t give a second thought to those sort of mainstream activities and just walk into any space, no matter how bright the lights, like I own the place. I really have no idea where this comes from, but I’m sure glad I’ve got it. 

The Drive-in Drag show was fun; lots of social distancing, but despite the multiple large screen TVs it just wasn’t the same as being up close and personal in a club. And the drive-in part wasn’t like the nostalgia of a the gravel drive-ins of my teenage years. I don’t know why I was thinking it would have anything like the old school concession stand of a classic drive-in. In any case, we broke out the beach chairs, set them up in front of the car and settled in for the show. About halfway through, I went to freshen my drink and decided to go to the far side concession stand to walk past the stage and get a better view of the stage as well as strut around the sparse crowd a bit — a girl doesn’t spend so much time getting her outfit together to avoid being seen. Toward the end, Claudia and I got up and started dancing in front of the car and when they played At the Car Wash she pretended to wash Jes’s car — that Claudia is a dancing fool (I say that with genuine love) and it was great to see her finally getting a chance to dance her heart out. 

After the show we headed back to the hotel and sat in the courtyard, talking and drinking, until some rather drunk person joined us and instantly dominated the conversation. Pretty quickly we decided to call it a night as Jes departed and Claudia and I headed up to the room — her to deconstruct and head home and me to pass out from my long and exhausting day. 

In the end, the highlight of the weekend wasn’t the show or any other particular activity, but getting a chance to reconnect with friends and feel a little bit of normalcy in the midst of this crazy pandemic, which seems like it has no end. I really feel blessed that that I was able to get at least a couple days off from this insanity.

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Tags: crossdressing, featured, Out & About

Category: Out & About