One Date At Three Bars

It all started with a match on a dating app. Now, I am not new to being matched with dozens of people on dating apps, as I write highly desirable “About Mes” and take amazing profile pictures. I get matched with different people, and then never respond.

No personal reason as to why I don’t respond, I just choose not to. The guys I am matched with just never really catch my mind or heart. I read their profiles with the most open mind, and still feel no reason as to why I should bother. I have set up countless dates and flaked on all of them.

I’m in a committed relationship with my lack of commitment. 

This brings me to my most recent of dates. This was a man that I have flaked on more than once. He offered to take me to my favorite bar, my favorite restaurant, my favorite spot, anywhere I wanted.And I just replied “k”. There was no feeling of guilt when I flaked. It was just something I became custom to. It was my new norm. Something I knew was true about myself, but never added to my dating profiles. finally, after months of neglecting to see this man I was actually interested in, I decided to put in more effort in my texting. Instead of the usual one letter replies, I wrote back questions to plan when and where we will meet for our date. He was very nice in allowing me to pick to place. However, since I flake on most of my dates, I was limited in knowledge of the best dating spots in town. So I picked something I have only been to once before with a friend. The place I picked was a rooftop restaurant, and the date I picked was Friday evening after work.


I was actually pretty nervous for this date. I never flaked on this man because I wasn’t impressed or interested, but only because I was happily married to my refusal to commit. But now with the divorce papers being finalized, I was scared to put myself out there. I picked Friday as our meet date to give me time to prepare. I needed a hair cut, a new jacket, laundry, clean my room in case he wanted to sleep over, buy gum, all that jazz. That Friday, I had my outfit all planned out and ironed and ready to go. I wore a Zara spring blazer, H&M full black slim pants, grey v-neck, and a Banana Republic clutch bag. In my bag, I was sure to only carry my wallet and cell phone. I normally carry cigarettes with me, but since I wanted to actually date this person, I didn’t want to gross him out with a nasty habit. I put my phone on silent and walked over to our meet him.


We met on the roof. Like most first encounters, it felt quiet at first. Sure we have talked before through text, but this is the first time in person. We did normal chit chat of how our days were, what we did, and how we felt about said days. He recommended me a few things on the wine menu, but I went with a cocktail. Small talk kept going up until my cocktail came. I got a Hummingbird, which was a tequila based drink. It was the color yellow and red, just like the colors of the light on the rooftop. While I didn’t enjoy our conversation too much, I did enjoy having romantic company in such a nice spot. Is this what I’ve been passing up all this time? Nice views and drinks? Our small talk didn’t get any bigger as the night progressed. He was a lawyer. A lawyer at a non-profit. He has traveled the world and seen so many things, and slept under so many different skies. He was so free from everything that bond me to where I am. Me, a corporate drone for profit. Too scared to take a nice vacation from my home. Eventually, the yellow and red sunlight that was on the roof died out and we were left in a blue sky. While I felt no connection with this man, and the chatter between us stayed as small as a fly, part of me wanted to keep going. We split the bill and left the roof. Once I was back on the ground, he asked what the rest of my plans are for the day. And I, in the most cheesiest of ways said “to keep hanging out”. And that is what we did. We walked over to our next location.


We walked together to a dimly lit martini bar. In this bar, the only light you see are from candles, and the only sound you hear is from a piano. We walked over to a table and placed our drink orders with the waiter. He recommended me his favorite flavor of a Lemon Drop, which was Raspberry, but I got Blueberry instead. Unlike before, our conversation began to really blossom. We spoke as if we had been friends for ages. We were getting drunk to the music playing in the background, as well as with each others company. We had more things in common than I thought. While I definitely do not have the same lifestyle as he did, we both did enjoy the same type of music. We both loved to watch horror movies. We talked about the highs we have enjoyed the most. Our favorite sexual positions that we both liked. Eventually, so much time had passed by that the night sky was just as dark as the bar we were in. As we finished our drinks, our candle lit table finally dimmed out. Which meant it was time for us to part ways. In a very childlike manor, I didn’t want the night to end. I was having fun with this person. We were finally finding similar interest and things we shared. I paid for the drinks, and walked outside, and he followed behind me. Once outside, he said he wanted to go to his favorite bar. I stood there quietly thinking he was going to go alone, but he asked if I wanted to join him.


We walked over to his favorite bar. It was this nice bar built from the buildings basement. He recommended me his favorite whiskey drink, and I ordered it. As we sat there drunk, we began to get into a more serious conversation. Why we were both single and dating. I gave the honest response that I was simply young. I was simply looking for the right person to be in a relationship with. That is all. I defined the right person for me as someone who was serious about themselves and their career. Someone okay with being apart for time in order to pursue personal goals. A very simple want that is hard to find. Then it was his turn to share why he was single. His reasoning being that he was looking for someone to be serious with. When I heard that, I got excited. Finally someone who also is after a more serious partnership rather than one night stands or casual dating. But then he added, that he was looking for someone to have a family with. That last part kind of hit me harder than the cocktails. A family? As in kids? But I myself feel like I’m a kid. No way can I say I was ready to get married to a person and have kids. I just got out of a bad divorce with lack of commitment, and now another possible proposal gets in my way. After he talked a bit more about what he wanted, I said in the most serious (but calmest) tone “I’m not what you are looking for”. It was the weirdest rejection ever, because I was rejecting myself for him. But it was true, I’m not right for him.  After saying the truth, I asked if we could go watch scary movies at his place, and he said yes.


We spent the night together. We came to a new goal since the one of relationships did not work out. Once we met that new goal, we both laid in his bed and cuddled and went to sleep. He was able to fall asleep peacefully, while I laid there in his bed. In a way, I was kind of sad that is how the night ended. I didn’t intend to go this far on the first date, but since there was no forward with us, I felt the stop should be left with a performance. Even then, it was a reminder as why dating is so hard for people. Dating is when two people have had their own lives, and try to bring those lives into one. Sadly, our lives were at two different ends and those ends did not meet. I laid in his bed the entire night awake just thinking, “this is why I have been flaking”. It was good to finally get a good grasp as to why I have been avoiding dating. This was a nicest vacation I took away from my usual norms, and was happy for the experience. I waited for the sun to rise, gave him and hug and kiss goodbye, and took my walk of shame home with my head held high.