I’ll Drink to That!

By Tina Davis

A rare opportunity arose on January 3, 2025 when I had a lengthy break during an event where my wife did not join me and I was staying at a hotel closer to the venue. I hadn’t made the schedule, but when I saw the amount of time in between my shifts, I started to make plans. I knew it might be my last chance for a few months, so I wanted to make the most of the time.

I ordered a new pair of knee-high black boots with a block heel from Amazon (using a gift card from a previous event) and sent them to a pickup spot closer to the hotel where I could stop on the way there. I had originally planned to wear a black top and black print skirt, but changed my mind and packed a mod print dress, keeping the black outfit as a fallback, after seeing a similar look on a woman while out for dinner on New Year’s Day.

I went to a local nail salon in male mode after leaving the event early in the afternoon for a manicure, getting a creamy beige color on my fingers. I wanted to keep the color on for the weekend while volunteering at the event, so any highly feminine colors were not going to be a smart plan. I checked into the hotel, got up to my room, unpacked everything, and got myself cleaned up and shaved. I made sure to do my hands and forearms, as the dress has three-quarter sleeves and I wanted to wear my chain-link bracelet with a sparkly heart.

The boots fit perfectly – I have differently sized feet but found that I can fit into most US women’s size 9.5 closed-toe shoes and boots. For open-toe sandals, I can fit either 9 or 9.5 depending on the heel height. Yes, I know how fortunate I am to be able to buy women’s shoes almost anywhere.

I got dressed and did my makeup, with false eyelashes adding a touch of Friday night glamor to my look. Then I put on my wig, zipped up the new boots, and started taking pictures in the room. It’s so much easier now to snap several times for each pose using my tripod and remote. I remember when I first started taking my own pictures, I would have to set the timer, click the button, and then dash to my spot and pose. Repeatedly. Never mind needing to set the phone up in a place where it wouldn’t fall over!

I had been looking prior to my trip for a place to go and found a martini bar and kitchen a few miles away from the hotel. I double checked my purse for what I needed, then took the elevator to the lobby and confidently walked out the front door, thanking the desk clerk as she wished me a good evening. The drive to the bar was uneventful, and I found a good parking spot along the side of the building. It looked crowded from outside, but since it was just after 5 PM, I hoped that there would be a seat at the bar.

As luck would have it, there was a perfect seat right ahead of me as I approached the bar. Several parties were being seated for dinner as well, so I knew this was a good choice. A middle-aged couple was to my right and a younger man was two seats to my left, the empty one in between us. I glanced at the menu but had already decided on what I wanted when I looked on their website. I ordered a classic vodka martini with olives, and when it came and was poured in front of me, I had to take a picture (see the top of this post) – it looked amazing.

Of course, it was so full that I spilled a little trying to pick up the glass! The woman to my right spoke up and said she had had a similar problem. I didn’t realize they had straws available – as a martini purist, I wouldn’t have used one anyway. After I ordered the coconut shrimp appetizer, she and I chatted for a minute before the two of them left.

Within the next few minutes, another woman arrived to take the two seats to my right, and a second man sat immediately to my left. The woman and I connected right away, as she asked if I minded her sitting there. She was waiting for a female friend who was running late, so I happily talked with her. We covered many topics, including her musician boyfriend, why I was in the area, and she even asked me if I was married (she noticed my CZ bridal set of rings). It felt both natural and strange to chat so easily, as I am a huge introvert and usually avoid “small talk” with people I don’t know. I even joined a quick conversation with the man to my left and one of the bartenders.

As I was finishing my martini, her friend arrived and decided to sit on the other side of my new friend, who had ordered her drink after some light coaxing from me. We had talked about the restaurant itself earlier, so she simply said to her friend that she had spoken “with her” about getting her drink without waiting. Since I was the “her” in that sentence, I was beaming with pride.

I needed to use the women’s room, so I grabbed my coat and purse and made my way over. Thankfully, a stall was open, so I used it appropriately, readjusted my hip pads and shapewear, and stepped out to find another woman waiting. I nodded to her as I went to the sink, washed my hands, and re-applied my lipstick before exiting. No glares or looks, no angry patrons, and no issues with my appearance.

I drove back to the hotel and quickly changed into male mode for my late shift. I was sad that I could only get those few hours, but happy that I had enjoyed the time out. My expectations were easily met and exceeded yet again, leaving me anticipating the next time that Tina will appear, whenever that may be. As the title of this post says, “I’ll drink to that!”

Hugs, Tina