Gender Shakes and Paint the Town

Back in August I attended an event called Gender Shakes, which happened to be in Chicago. In contrast to Pinkfest, which is a 6 day affair with 4-5 activities each day, Gender Shakes was much less ambitious. It was just 2 days, Friday and Saturday, and only had 3 official activities–a meetup in Boystown each night and a group photo at the Bean on Saturday afternoon, followed by some shopping. Before we get to the details of the weekend, I’d like to talk about a unique aspect of Gender Shakes. 

After I registered, the organizers, added me to a Messenger group chat and also provided a link for me to join something called Discord. This gave me the opportunity to meet, at least virtually, the other attendees. Of course, getting to know people online is nothing compared to meeting in person, but it was significantly better than showing up the first night without knowing a soul. The other advantage of the pregame chat, was the opportunity to self organize unofficial activities. As you might expect, our heroine Julie took full advantage of planning off-schedule activities–that’s just how she rolls. 

“Okay Julie, I understand the group chats, but what’s that Discord thing you mentioned?” Apparently, it’s all the rage with the youngsters. (Oh yeah, Gender Shakes is a younger group and I was probably one of the oldest in attendance). I’m guessing you’re familiar with being in a Messenger chat group. I don’t know if you’ve ever been in a large chat group (this one was about 15-20 people), but I find them to be hard to follow, because the topic of discussion changes so frequently. The advantage of Discord is that it has separate topic channels, so multiple conversations can be occurring in parallel. It did require me to install the app on my phone, but that was super easy and I found that using it was rather intuitive. The other cool part was that after the Gender Shakes weekend, the online relationships continued. It’s been over a month and the Discord conversations are still quite active–typically a couple dozen posts each day. 

Friday afternoon outfit.

Alright, let’s get to the action. The hotel that most of them stayed at was the Best Western Hawthorne, which is basically in Boystown. I looked into staying there, but there were Cubs games both of those nights and the air show that weekend, so the prices were kinda crazy. I ended up getting a hotel in the loop–still kinda pricey, but much more reasonable. Of course, this meant that I was a bit isolated from the group. But, that’s not new for me, so I wasn’t too concerned. Per my usual MO, I got a manicure before checking in on Friday and planned to do a little window shopping that afternoon. Shopping is more fun with friends, so I checked the chat group and noticed that Natalie had arrived early and was out and about, by herself. So, I sent her a dm and she was happy to meet me at my hotel, once I completed the process of getting my Julie on. After a bit of shopping, we decided to go for an afternoon drink at the rooftop bar in the Virgin Hotel–spectacular views of the city. We had never met before, so it was cool to have an hour or so to just hang out and chat. At 5:30, we parted ways to our respective hotels to get ready for the evening. I should have taken the short train ride back to my hotel, but decided to walk it. Turns out that was a bad decision, because the super cute wedges I was wearing did some subtle rubbing on my feet, which kinda gave a bad start to the weekend.  

The official schedule had no dinner plans, so a few days before, I took advantage of the chat group to organize a dinner group at an Asian Fusion place called Pingpong. I’ve been there several times with Claudia and Jes, and it was perfect for this group because it’s only a block from the Best Western Hawthorne. Taking the train up there, I wisely wore flats, with my heels in my purse. There were eight of us for dinner and the casual atmosphere was a great opportunity to get aquatinted–just about everyone was meeting everyone else for the first time. We had all met virtually, but as you know, meeting in person is a totally different animal. After dinner we stopped back at their hotel to freshen up a bit, which as you might expect took longer than anyone expected. On my suggestion, as one of the few locals, we skipped the Ubers and walked to Charlie’s. Turns out that walk was a lot further than I remember, especially in the ‘slaying’ heels that we were all wearing. That combined with the wedges of the afternoon, meant that my feet would be far from happy the reminder of the evening. Shoe issues aside, another advantage of the pregame chat was that someone had suggested we designate Friday night as LBD night. Just about everyone took that to heart and I must say that we were fantabulous looking group. I didn’t exactly wear a LBD, but my black bodysuit top and black skirt with diamond studded mesh, fit the bill perfectly.

Charlie’s had a drag show that night, so most of the night was spent watching the show. Given my footsie situation, it was probably a good thing we didn’t do much dancing, cuz I’m not sure how long I would have lasted. At Charlie’s, I got to meet most of the other folks, although I struggled a bit to connect the in-person faces with online persona. Didn’t help that it was low light and lots of folks were wearing masks. 

The next morning I was up pretty early, despite the late night, and managed to make it to the Bean by noon. As I usual, it was crazy hot at the Bean, with tons of sun. Also, as expected, many of the others were late at arriving and the organizers were way to generous about waiting to get them into the group pic. It kinda dampened the mood and I think is a bit reflected in the resulting pic. I did get some nice individual shots and a great selfie while I was waiting around under the shade of a tree.  

After the Bean, most of the group headed off to Michigan Avenue for some Mag Mile shopping. I’ve been trying to keep myself on shopping budget and I’m not sure my closet can hold much more, so I organized a small group (Serna, Emmi and Natalie) to join me at the Art Institute. It’s right across the street from the Bean and I have a membership, so we basically got in for free. After the Art Institute, I needed to get back to the hotel to get ready for the evening. My Chicago wing girl Claudia was joining me at that point and we had several activities planned for before meeting back up with the group at 9:00 p.m. The other three were looking for some food, so I suggested Miller’s Pub, just a block from the museum and they seemed to thoroughly enjoy classic Chicago ambiance. 

When I got back to the room, the Claudia transformation was in full swing. I got busy with glamming up my makeup and doing an outfit change. On the agenda was an early dinner, just the two of us at a sushi place in Boystown, and a burlesque show at the Newport Theater. The show was at seven, which gave us plenty of time to make it to Roscoe’s by nine. I was determined to slay that night, so I went with my silver sparkly dress that I think many of you have seen before. While waiting for our Uber, a random woman in a car waiting to pick someone up, gave me a few compliments. So, the evening started with my confidence being through the roof.

At the sushi place we were pleasantly surprised to find that they had a happy hour going on–yeah, that’s how early our dinner was. We took full advantage and ordered almost more than we could eat–just kidding, I could never get my fill of sushi. The Newport show was, of course, amazing–I have yet to be disappointed by a show there. Emmi and Serna ended up joining us and were equally impressed. Oh yeah, just before the show started, a random guy at the table just behind us, tapped me on the shoulder, just to compliment me on my outfit–I think I might have succeeded in my slaying goal for the night. 

Roscoe’s is just a block from the Newport and was the perfect venue for Gender Shakes. In the front of the bar we commandeered several tables and were a flurry of mingling as people moved from one conversation to another. As people got a few more drinks in them, most notably the pitchers of blue stuff, smaller groups headed to the dance floor in the back of the club. New friendships were definitely solidified that night. Sunday morning, the chat groups were buzzing with war stories from the night before and folks making plans to get together for brunch before heading to the airport and dispersing across the country. 

“Okay Julie, sounds like Gender Shakes was tons of fun, but what’s this “Paint the Town” thing?” Great question. Thanks for asking. Paint the Town is a new event we’re putting together, where we’re hoping to combine the best aspects of GS and Pinkfest. By the way, Pinkfest was just last week and I will be giving a full report on that next month. 

The main motivation behind Paint the Town is to move the date to a time of year where Chicago hotels are cheap. This will allow us to have a central hotel in a great downtown location surrounded by tons of amenities. Unfortunately, that means winter. Specifically, we’re targeting the first week of February. I know, I know. You’re thinking, Chicago in February? That doesn’t sound like much fun. But, as a local, I can tell you that the city is totally open and the nightlife around here doesn’t stop just because the outside temperatures are a bit lower. Okay, maybe a lot lower. But, it’s plenty warm inside all the great restaurants, theaters and clubs. You’ll just need to get yourself that fabulous feminine coat you’ve been eyeing, so you can stay warm while waiting for that Uber. Similar to Pinkfest, we’ll have activities scheduled throughout the day. But, instead of 6 days of activities, we’ll just be doing Thursday, Friday and Saturday. 

The part I never liked about Pinkfest is that most attendees have no idea who will be showing up to which events. And, for newcomers, everyone is a complete stranger. That wasn’t such a problem for me, but not everyone is a social butterfly like Julie. This is where we’ll be taking a page from Gender Shakes. Everyone who registers will be invited to join our dedicated private chat groups (we’ll be using Messenger and Discord like they did with GS). We expect there’ll be lots of pregame banter, so you’ll get plenty of opportunity to meet folks virtually before meeting in person. Also, we’ll be developing the detailed activity schedule through the chat groups. I know lots of cool stuff to do in Chicago and will be making tons of suggestions, but we want to make sure the official schedule of activities aligns with the interests of the group. Of course, if the official activity of a particular night is not your thing, you can always go to the group chat and self organize others to join you with alternative plans. We don’t need, or even want, a massive group blindly moving from one activity to the next. Our interest is more along the lines of creating a community that drives the activity schedule based on individual interests. If that means parallel activities and smaller groups, that’s perfectly fine. The more important aspect is to develop new friendships that will germinate before the event and hopefully extend long after the three days of the Paint the Town. 

If you wanna know more about Paint the Town, here’s our new, hot-off-the-presses website.  The registration site is not yet open, but is expected to be up and running in the next week or so. Please feel free to send me an email if you have any questions. We’re looking forward to seeing you in February.

Tags: crossdressing, featured, Out & About

Category: crossdressing, Out & About