The 2:30 a.m. Uber

Here’s the thing with pocket squares and movie-star smiles and lofty one bedroom apartments- if they seem too good to be true they probably are.

Anyone who has ever read anything by me before might remember that I’m what I like to call a “realist”. Most would maybe switch that word out for pessimist or perhaps even cynic, but I’m the one penning this story, so it’s my verbiage that will ultimately make its way in. Anyway, yes, I’m a realist. I approach scenarios matter of factly, and while my “no nonsense” attitude has boded me well in many aspects of my life, it unsurprisingly hasn’t been my most charming feature with regards to my dating life.

So when I was faced with what had appeared to be the most ideal suitor I had encountered, I made my best attempts to keep my cynicism at bay.

Mr. Tall, dark and handsome had it all. Stunning good looks, engaging conversation skills, a jovial personality and laugh, and a nice, spacious one-bedroom apartment.

This could very well be game over, I thought after our third date.

He dressed well, spoke well and made sure to carry out conventional habits of courtship, (i.e. paid for dinner, Ubers, drinks, etc). There wasn’t an air of discomfort of awkwardness in the initial few dates, and things seemed to be going swimmingly.

But like any shiny new car, before driving off it’s important to check under the hood…

I’m not implying that after getting to know each other I was met with deviant desires, or a closeted gay or anything dramatic like that, but what I will say is that our compatibility became inconsistent, and at times, uncomfortable.

While I was still ultimately charmed by his good looks and redemption kisses, I was off put by interactions more times than one, and began to feel like I should be on guard, versus more comfortable. (Did anyone happen to see my “sex-den” Snapchat?)

It eventually fizzled out for the very reasons above, awkward interaction, uncomfortable dialogue and ultimately difference of personality, but not before I had enough time to turn the “another one bites the dust” narrative into a lesson:

While undeniable charm and tailored clothing and Crest-commercial smiles make for a very strong initial draw, you need to spend quality time interacting with someone before browsing Vera Wang’s bridal collection.

I also realized that perhaps instead of feeling strange and Ubering home in the wee hours of the night, maybe I should use my communication skills and voice that things are feeling ~strange~.

Afterall, it’s not like he’s a mind reader. 😉


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