A Couple Days in Wicker Park

Outta the blue, I get a text from my friend Tina, “Let’s go to a French restaurant.” This seems a little odd, cuz the last time I saw her she was really, really concerned about Covid safety. It’s even more odd, because I know the French restaurant she’s suggesting — her favorite place, La Bouchon in Wicker Park, which is really small with only indoor seating. We negotiate a bit on a date and settle on the first Thursday of October. I start planning my accommodations and decided on an Airbnb that I’ve stayed at before — it’s one train stop from the heart of Wicker Park — basically Milwaukee Avenue between Division and North Avenue. The plan was to get an early check in (one of the reasons I opted for this particular Airbnb) and get in some afternoon shopping on Milwaukee Avenue.

Arrived at the the Airbnb at 11:30 a.m., dropped off my bags and headed off to the nail salon — a new place I’ve never been to before. As usual they didn’t even bat an eye when I selected several pretty colors to choose from. Decided on a light powder blue and on the walk back to the Airbnb (in boy mode), I was noticing how attention grabbing and pretty that color was — I really love experimenting with nail colors. 

As usual, makeup and figuring out an outfit took longer than I wanted. I decided to go with blonde hair and again with the nude lip color for the more daytime look. Bare legs with a shortish black dress and my black suede boots — first time pulling out those fabulous boots this fall. Of course, the look is finished with one of my Kate Spade purses.

Got a few mirror selfies and I was finally out the door around 4:30. Soon after, I was walking up the steps from the blue line at Division and Milwaukee — trying to keep my shoulders back and maintain proper feminine posture. My plan was to check out the cluster of wig shops in that area. The one called Heads and Threads, I’ve been wanting to visit for some time. I could have easily visited some other time in boy mode, but from my other visits to wig shops I’ve learned it’s almost impossible to determine if the wig will work out without makeup. So, I figured this will be the perfect opportunity to make a good decision. Of course, my plan was thwarted by the pandemic, cuz all three shops were not allowing customers to try on any of their wigs. I suppose it was for the best, cuz I wasn’t seeing anything I really liked — the quality was quite low and I’ve had enough experience with low quality wigs. Another Covid related issue was having to wear a mask in the stores, which was causing me to overheat, especially after coming in from the moderately cool October weather. In Julie mode, I’m always having problems with body heat regulation — either too hot or too cold. 

After the bust at the wig shops, I continued my walk up Milwaukee Avenue, but now on the hunt for thrift and boutique shops. I, of course, stopped at Buffalo Exchange where I tried on a couple skirts and some jeans, but wasn’t really feeling them enough to buy. Then, I stumbled upon a boutique shop called Free People — a fairy upscale place with prices to match. I first noticed some cute earrings, but too expensive. Then, I noticed a denim mini skirt. Got the sales associate to help me find my size, which wasn’t really my size but the largest size they had. It had a bizarre cut on the hem that I didn’t like, but in the fitting room I noticed that I could be without my mask and had a chance to get a little regulation on my body temperature. So, I figured I should look around some more to see what else I could try on — almost as an excuse to hang out in the fitting room some more. I found this interesting corduroy mini skirt along with a T-shirt like top. It was actually an awesome combo, but the top was a little too low cut for my liking and the skirt was definitely too tight around the waist. In any case, I got some great pics, which kinda made a success of the afternoon. I’ll be on the lookout for a similar, more appropriately fitting, outfit in the future. The sales associates were super friendly and not at all concerned that I was leaving without buying anything. 

In the dressing room.

After shopping, I planned on finding a coffee shop or restaurant/bar with outdoor seating and hangout until it was time to meet up with Tina for dinner. But, I wasn’t seeing any places I liked and it was getting a bit too cold and breezy to be hanging out outside, bare legged. I was pretty close to the North Avenue train stop so I decided to head back to the Airbnb — additionally motivated by being a little concerned that all the mask wearing had made my makeup sweat off my chin and upper lip. Back in the room, I quickly removed and reapplied my makeup, just in those areas and put on some fun, large polka dot tights. Also, changed to some darker, more dramatic lip color. Time was short and I was glad that the Uber route took the highway, so we were at the restaurant in under 10 minutes, which got me there a little late, but 5 minutes before Tina. It was great to see her and of course we had a great conversation. A few minutes in, she noticed me looking at my tights and commented, “Cute tights”, which I really appreciated. Tiny complements like that are something I love so much about Julie time — definitely something that never happens in boy mode.

Being a French restaurant, we, of course, ordered the escargot appetizer. Unfortunately, minutes after it arrived, and before it even cooled off, Tina spilled her drink and much of it landed in the food. She was very embarrassed, but the waiter was super nice and insisted on bringing us a whole new order. As you might imagine we left a massive tip — way larger than the 30% standard that I have adopted since the start of Covid. Oh yeah, to her concerns about safety. She admitted that this tiny restaurant was not ideal, but she felt that her health was in better shape than the last time we met and that we, as a society, were in a short window where such risks were acceptable and didn’t want to miss the opportunity to visit her favorite restaurant.

Lauren and Julie.

After dinner, I was gonna suggest we go to Lottie’s Pub — not too far away and it looked like they had outdoor seating. But, before I could say anything, Tina suggested we go to Reed’s Local — a dive bar in Avondale. She had brought me there before and I really loved it, so there was no way I could resist. It’s mostly an indoor place but they added some outdoor patio space in the back, which is where we spend most of our time. While I was getting a drink, I noticed that the Bears game was on — Thursday night game and it was in the last two minutes. There was a time when I was pretty regular about watching football, but since Julie has become a bigger part of my life, I’ve pretty much lost all interest — I believe those two minutes were the first time I’d watched a game all year. Then, from across the bar I hear, “IS THAT JULIE SLOWINSKI?” I look up to see Lauren. The last time I was there, we randomly struck up a conversation, ended up taking a bunch of crazy pictures and became Facebook friends. It was so cool to see her again in person and get some updated pics. Turned out to be a late night and after deconstructing I finally got an Uber home around 3 a.m. 

Day 2:

The cute tights.

Before Tina had contacted me, a Facebook friend, who I had not yet met in person, contacted me because her and her wife were planning to visit Chicago on a Friday night and hit up Boystown (about 2 weeks after the Tina night). Friday’s are usually tough for me, but I told her I’d try to make it. The plan was to get my kids to grandma’s house after their school and make it back to the hotel early enough to meet them in Boystown around 8 or 9. I also needed to drop off the car at my wife’s work and then take the train. Yeah, it was gonna be tight. The upside was with the kids at grandma’s for the weekend, I could spend the night at the hotel and get a full Julie day on Saturday. So, I contacted my bffs about joining me for dinner and drinks that Saturday night. Claudia was all in, but Jes and Danielle were unavailable. However, our friend Naomi had just gotten back in town, after being gone since the beginning of the pandemic. So, we were a solid threesome. 

I had found a perfect hotel in the loop which would optimize my time on Friday night and be very convenient for shopping on Saturday afternoon. Given that base, Claudia and I went into planning mode — scouring the internet and proposing restaurants and other activities to each other. At one point we were thinking about going to this Halloween themed popup bar in the West Loop. By coincidence there was going to be a Halloween parade just outside the hotel that night (even though it was a week before Halloween). I was really excited about pulling out my Darling Witch costume and making it a night. Then, I thought, “Wait, a Halloween parade in the middle of a pandemic?” After some more intense googling, we found out that our info on the parade was from an outdated website and it was actually cancelled. That put a damper on the idea of wearing a witch costume a week before Halloween, so we kept looking. We were thinking about a socially distanced dance club in Boystown or the jazz club we had gone to the month before and then some dancing at the open rooftop pizza place across the street. We finally settled on a place called Bourbon on Division to see this startup band Siblinz on their rooftop deck. It was a few blocks from this Speakeasy called Bordel that I once visited to see a burlesque show. There would be no show that night but it’s a cool place and we planned to go there for some late night drinks and maybe some low key (i.e., socially distanced) dancing. We only needed to figure out a place for dinner and everything would be set. 

About a week before the big weekend, I texted my parents about taking the kids. They didn’t reply right away, which made me concerned. Eventually, I got a call. Seemed that my Dad was sick, turned out to be shingles, and it was unlikely they could have the kids over. So, my plan was in shambles. I immediately texted Claudia and we tried to come up with alternatives, including moving the plans back a week. We decide to press on with the original plan and I got my wife to agree to be alone with the kids that Saturday night, despite working the entire day. The downside is that I needed to give up on my Friday night and Saturday morning/afternoon plans. It’s really too bad, cuz I had a super awesome outfit planned for Friday night that would have been perfect for Boystown in the fall — suede boots again with jet black hose and a sparkly skirt that’s way too short for me. 

A day after I got my wife to agree to this alternate plan, she texts me about the sudden change in Covid restrictions — Chicago was going back to ending all alcohol sales at 9 p.m. and bars and restaurants must close by 10 p.m. So, we had to move all of our plans to earlier in the evening — dinner now at 5 p.m., Bordel was out and planning for some drinks in the hotel room after seeing the band.

While all this is going on, a super cute plaid skirt pops up on my Facebook feed. It’s too expensive, so I try to ignore it. I eventually succumb and schedule for an in store pick up at Loft. I get the skirt home and discover it’s kinda loose. This is odd cuz I’m almost always a size 12. A couple days later I bring it back to see if a size 10 will work better. In boy mode, I explain my problem to the sales associate and ask if I could try on the 10. It fits perfectly — apparently my diet and workout schedule is having an impact. At the counter for the official exchange, she tells me I’m gonna get some money back. Apparently, the skirt is now 50% off. Double bonus for Julie that day. Yay! Given everything else that was going on, I definitely needed that boost.

Saturday finally arrives and I’m able to get to the hotel around 2 p.m. — about 30 seconds before Claudia. Usually I arrive a couple hours before her, which gives me a head start on getting ready, cuz I usually take longer than her. I was especially hampered because I didn’t have time to visit a salon to get my nails done, which meant that I would have to do them myself. They turned out ad a total disaster, with smudges, nicks and polish all over my cuticles. As I was hitting my final touches, figuring out jewelry and fixing my hair, Claudia was tapping her watch and like, we need to go — 5 p.m. dinner is no treat. 

As we were driving down Division approaching the restaurant, I was like, “I’ve never been to this part of Wicker Park before. Look at all these cool restaurants, all with outdoor seating. We totally need to come back here, even after the pandemic.” Dinner was awesome, as was the conversation. Naomi filled us in on her travels and we reported on our Chicago outings during the pandemic. The bar with the band was just around the corner and we arrived 5 minutes before the scheduled 7 p.m. start. The bouncer at the door said they were not admitting people to the show yet, so we hung out a bit. As we waited, a couple of women, dressed to the nines, walked by and went in. I thought, “Okay, maybe we won’t be out of place”. Going in, we were instructed to head to the 3rd floor — apparently the others went to an engagement party on the second floor. We get to the 3rd floor and we are the first to arrive and the band is still getting setup — it was actually an hour later before they started playing. That was fine with us, cuz we got to get drinks, take some pictures and chat with the band. The only problem was that it wasn’t outside. I was imagining a rooftop garden patio with heat lamps and such. It was more like a 3rd floor loft that was converted into an entertainment space. It’s probably better, cuz it was kinda cold that night and we probably would have been freezing. After the show (which ended at 10 p.m. — remember the newly imposed city rules) Naomi headed home, and after getting some late night french fries, Claudia and I went back to the room and chatted for a couple hours. Then, it was time for both of us to deconstruct and head home. Well, it wasn’t the two days of ‘up until all hours of the night’ Julie time, I had originally planned, but it was still a really great time, mostly because I got to hang out with great friends. And, during a pandemic, or anytime for that matter, that’s what really counts. 

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Tags: crossdressing, featured, Out & About

Category: crossdressing, Out & About