The Single Life: Date #7, Mission Analytical

Analyzing any situation good or bad, can get out of control even in beautiful surroundings..

Analytical tendencies and mistakes, I made a terrible one and took a coworker’s advice because this was the week of overwhelming dates and opportunities and this date could’ve been better but before I get to this point, let’s start from the beginning of the week..

My Date: Let’s go to this place in the Mission, they have tasty drinks….

Co-worker: You should go to your date absurdly drunk, it’s probably fun and you’ll experience something different for a change?


At this period, I already experienced in one week a streak of dates ranging from impromptu photography,  cheesy flower antics, and political charged discussion and now tonight’s date. This entire week, I was texting this person and three others to fill up the next couple of weeks. I was on a roll, it wasn’t an entirely positive one but I made it happen somehow.

Exchanged messages with this one lady, who’s love for bacon and data knows no boundaries. We had good “text chemistry” but the real deal had to occur within a week and a half. When you get back into dating, especially this 2018 version everyone knows and loves, the lines to really blur and the timelines become unexpectedly complicated. You see unlike project management, where its expected to have a “moving deadline,” dating wise one of the biggest struggles is this idea of the “stake in the ground” commitment of the first date.

Surrounded by technology and some of the most influential companies in the world, you’d think we would find a solution to this problem. That isn’t the case and as each day and text went by, my fatigue began to show. In my current career  the hours are demanding and technical challenges are always an expectation. My day to day can easily change in a blink of an eye unlike most roles. However I crave stability, predictability and the occasional good morning text that someone would give just to add a little extra perk. After the busy workweek was over (thursday night, is an early start for most professionals and young adults), things got a little out of hand at a bar we frequented within the downtown area. One drink, after another, turned into four glasses of truth serum.

One by one, my co-workers and friends kept asking me the usual questions and banter,

“How was the last date?”

“What happened with xyz?”

*insert relevant dating cliches and platitudes here*

My mind began to wander and as I received the last text from my date tonight, “Can’t wait to see you tonight.” I asked if any of my co-workers wanted to come with me pre-dinner before meeting up with this person. One of them accepted and we conversed about nuances of life and the complexities of dating. I paid my share, gave my friend a hug, and off I went to this analytical lady. I entered the bar and it was a familiar scene, a mix of cardigans, tech hoodies, and handlebar mustaches. My black horn rimmed glasses, didn’t help painting the cliche portrait but I had to fit in somehow. As, I stood in my corner in a semi-drunken stupor, someone tapped me behind the shoulder.

She was petite, had her hair up, also with black horned rim glasses and a cute smile (it was my date for the night). Now painfully, this is where things get a bit more hazy than expected. We had several more drinks and exchanged the usual “dating interview dialogue.” However one thing that stuck out the most, was her simple words of, “You know, I have a keen sense of situational awareness as well…”

Now, this simple phrase wouldn’t bother me too much but it was at that time, I realized I don’t know why I even accepted the date in the first place. She was analyzing me as much as my inebriated self could muster some form of analysis. The body language, the levels of comfort, and of course the possibilities to go beyond the first night of sex. That lasting impression was made and it sealed my fate… That I was gonna go home alone that night.

Sure, she was great on paper and we had good conversation but this was one of those convenient and nothing better to do on a Thursday moments. I reflect back on this date, nothing really stood out, other than our in-person chemistry was lacking and my drunken self was disappointed when she called the night off short (45 minutes into it). Perhaps this is why, I decided to liquor myself up prior to meeting her, it served as a safeguard in case of disappointment. Sure enough, this strategy justified itself (in an aha-esque fashion) serving as a self-fulfilling prophecy (I’m a psychic, bitches).

Companionship and ease of conversation is probably one of the things I miss most, when it comes to being in a relationship.  Everyone puts up some sort of facade up, no matter how “real or one hunnid/100”  one claims to be. We like to project the best version of ourselves, even when we’re barely keeping it together deep down inside. As I walked home, I began seriously evaluating my dating filters, whether or not they needed some serious adjustments. Serial dating, really isn’t my thing, but one of the biggest mistakes I recently with someone I dated for a while, was putting all my eggs in one basket. It is the sole reason why I continue “stack/stagger” dating in this process because I’m sure all my prospects are doing the same for me. I haven’t found anyone worth investing from the jump and I have yet to meet woman that can securely say, “You’re the only one I’m dating.” And give me a reason, to purge all my apps and prospects for good. An idealistic sentiment, that one could only hope and dream of.

This old school mentality of dating, it was much more simple back then. I wish this generation wasn’t so infatuated with FOMO and the “grass is always greener” ideologies. Until that ideal woman comes into my life, the only thing I can do is: pivot, iterate, and find someone who embodies and smashes my bar of standards to smithereens.


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