Dating: A Commentary According to a Puritanical Male (GUEST POST)

Ok amigos, after yesterday’s spicier (some might say “salacious”) post – which was also slightly hyperbolic – I figured we should balance things out with something equally fun but a touch more appropriate and poignant.  And that’s the background on how I roped my friend Drew into writing a guest post for me.

Drew is one of my good friends from undergrad, but I’m going to spare everyone the embarrassment of a picture of those nerdier years (let’s just say we’ve both become significantly more attractive since then).  We are weirdly similar, even down to the same Myers-Briggs personality type (INTJ club for life), which has made him a great wingman and sounding board for guy problems. The main difference is that Drew manages to make his neuroses and social oddities much more charming. So we have a lot in common; he’s just definitely a better person to write a Valentine’s day post that consists of more than just a bunch of jokes about ballsacks.

(What can I say? A part of me has the same sense of humor as a 12 year old boy.)

Itty bitty disclaimer: I supplied the graphics here, so don’t judge Drew for the tasteless valentines within his post.

And with that, I’ll let Drew take it away…



Dropping the Ball

Our first date included both the itinerary of bell-ringing for the Salvation Army, dinner, and watching Anchorman 2. Despite that, we continued to go on dates.

It was our third date when we went to a New Year’s Eve party with a large group of her friends. Our group was large and required several tables; she and I sat with the couples (wink, wink). Afterward, we went to someone’s house for a party where people were playing card games and casually chilling on the couch. It was great, but if there was ever a death knell to a potential relationship (which honestly I was completely wrecking anyways), it would be realizing that when the ball dropped in Times Square you were nowhere near her and were instead screaming while hiding under a table playing “murder-in-the-dark” with strangers. Granted, this shouldn’t have come as a total surprise because when I initially asked her out I failed to give a time, place or activity and had to reapproach her to give her the pertinent details. Honestly, at this point I need someone to guide me through the dating process.

Since you, the reader, now see that I am essentially the perfect male specimen and a hybrid of Gosling and Bond’s suave charm, I should probably explain a little bit about myself, given who I am is frankly the crux to my perspective.

Great Expectations

I am a remarkably average twenty-five year old male. When I say “remarkable” I mean: I frequently get called “Kevin”, “David”, and “Josh” by complete strangers, people hand me their things (e.g. stroller, puppy, or laptop) while they run to the restroom, and my students like to guess which clique/stereotype I fit into during high school while running through an exhaustive list of guesses (answer: I did nothing). Ah, yes, I am also a high school English teacher; which means I leverage synonyms, have exceptional patience, and “an extraordinary gift for hope” (Fitzgerald, 1925).

I should also preclude any discussion about my perspective on the dating process by confessing that I have really terrible expectations and motivations. Is it too much that I assess dating prospects by “ETA until couple’s Halloween costumes”, “does she like spicy food enough to eat my stir-fry”, and “will she duet with me to my Disney playlist”?

Dating Failures

Another date ended when the girl insisted we get snow cones instead of food, so here I am looking like the Joker while she struggles to make conversation. Our conversation nearly ended in my choking to death out of shock when she made the next comment. She noted she saw me reading one time, I explained in less than 10-seconds I was reading a Stephen King book (which really is a minor miracle with me). She then said, “I don’t know, I see books and think- reading is a waste of time.” I was incredulous, clearly she doesn’t know and doesn’t think. I love fiction and in fact, I am an ardent supporter of the 2nd Amendment; the right to bear false witness. The conversation went downhill fast when I learned she was casually suspicious that my church was a cover for an underground drug operation. So that one isn’t necessarily my fault.


How about a first date I called off once the girl pointed at an item and commented how nice it would look in our future home? Oh wait, that’s right, I didn’t call it off. Instead our noontime lunch date ended after dinner and dessert at 9:30 PM because I didn’t know how to politely end it. The deal-breaker, for me, was that she confused Schmee (Captain Hook’s left hand man, get it!?!) with one of the Seven Dwarfs as we walked past a Disney themed painting. I realized then and there that I need a girl who can at least appreciate my nerdy trivialities and someone who can’t even recognize The Jungle Book certainly won’t be as hyped as I was for the latest Pokemon game or Lego Batman movie.

Needless to say, I am inexperienced and have gone on few dates. I even consciously decided that January was enough effort (3 whole dates) that I deserve a month off. So I understand completely that my perspective does not anywhere match the norm.

Trust me, I do know some red-blooded males, but they probably refrain from sharing all but the Rated-PG content with me in the same way some priests wouldn’t even voice their proclivities with me in the confessional. No joke, in a moment of weakness I turned to reading Yahoo Answers to determine whether to hold hands on a third date… I may have also said as much to my date. “I have decided,” I announced, “that we should hold hands and walk under my umbrella.” During our stroll she may have been looking to see if I had a Lightning Port. This is the date that died from awkwardness when during the entire length of Finding Dory my arm fell asleep wrapped around her, I tried to fight through the sensation until it felt like my arm was on fire and I had to ask to reposition her resting head into my sweaty armpit. So, yeah, you could say I have some “game”.

Don’t even get me started on the date where we met at the Applegate Park Zoo in Merced, CA. You know, the one with the raccoon exhibit or the sign advertising the “domestic cat”.

“Swiper, No Swiping”

There is likely an issue when Coffee Meets Bagel suggests I either become less picky or increase the mile radius for potential matches to 250 miles. I read research on Tinder, as one does, which suggested women “swipe approvingly” on a third of matches while men swipe on half (quotes may be exaggerated). I definitely swiped “sure, why not?” on three of one hundred, before quitting. By “quitting”, I mean: swiping “no” as fast as possible and taking screen shots of the funniest profiles to send in a group text because what am I if not a hypocritical jerk.

For the ladies, these were my thoughts on Tinder profiles:

  1.     Snapchat filters:
    •     Lead me to assume the worst case scenario: you have some weird Pirates of Caribbean flesh-eating black-spot on your face
    •     Or, you are likely to ask me what I mean when I say “conceivably” or any other word with more than two syllables (never said I wasn’t pretentious)
  2.     Shots including magically both front and rear cleavage:
    •     Positive: you are really flexible and dedicated, likely taking several attempts at that picture
    •     Negative: you think they are your best assets
  3.     To the Woman handling a newborn calf coated in fluids/better moustache than mine/who looks like the girl from The Ring:
    •    It is okay to not date online

Now, to be fair, I definitely am not photogenic and chose what essentially are the only four decent pictures of myself (one actually looks like I possess biceps, so even if it’s not good, I still use it). But, I labeled each with a warning that I do not have selfie game. See, some self-awareness.


Playing the Dating Game

I have learned this: dating is the world’s largest and most complex massively multiplayer role-playing game. We all take into consideration our attributes and bravely quest to find the correct life partner.

The trouble is the role-playing. I don’t mean kinky Fifty Shades stuff, but rather that people strive to put their best foot forward and make positive impressions. As someone who really could be characterized as C3-PO, Spongebob, and Kuzco from The Emperor’s New Groove mashed together, it isn’t easy.

This is hard to maintain, particularly when it means someone like me also has to feign affection. I approached a dinner date with as much professionalism that my date commented, “Wow, this feels like an interview.” So now, I am so conscious of my body language and follow-up questions on a date I feel like Hannibal Lecter, minus the sociopathic tendencies.

But the great thing has been the growth and development I have seen in myself, as I grow more open to this reality; dating requires vulnerability and a good deal of awareness. The more I have put myself out there, the more I learn about myself and what I find necessary or unnecessary in a date. I have learned to listen more, lean forward and appreciate the uniqueness of each woman without comparison to the previous. I think I may have even begun to break down the Disney-programming that there is “one” for me, but rather that God will provide in due time the right person who does not need to be perfect but is perfect for me.

That all said, clearly I have a lot of work I need to do on myself. Maybe the right woman is one patient enough to walk me through it.



PS: Drew is hilarious on twitter. You should stalk him.


One thought on “Dating: A Commentary According to a Puritanical Male (GUEST POST)

  1. Athena says:

    Be honest, if it’s not working, or “feeling it” just say so,than both can walk away with their dignity.
    On the flip side if your totally in, open the door. Whether a car or into any kind of structure. She might say “you don’t need to do that.” But trust me she will feel cherished.


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