Thought Catalog

My First Girlfriend

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I’d like to come out and say that I have hit my sexual plateau. I’ve peaked. At first glance, this appears to be bragging of the most egregious kind. Nothing could be less accurate. Rather than basking in the copious amounts of satisfactory orgasms I’ve experienced in the past year, I have been sourly examining the ruins of my sexual history. This is as good as it will ever get, and for the rest of my short life, I am forced to look back on my teens and 20s with a mixture of juvenile lust and craven jealousy. I am trapped in a cycle of diminishing returns, with no hope but to retreat inwards.

It’s only natural to wax nostalgic when you realize your best years are residing in another zip code. I occasionally flash back to the glorious day when I beat Sonic the Hedgehog 2 without a friend playing as Tails. I even snapped a Polaroid of the event which I have pinned up on the wall next to my toilet. My greatest bouts of anxiety tend to occur in the lavatory, and the photo reminds me that I can scale any mountain with persistence and large quantities of Dr. Pepper.

There are many dark moments in my sexual history to ruminate on. I have endured terrible break-ups. I’ve had a girl leave me because she was afraid I’d turn out to be gay. To this day, I feel that I disappointed her. Tessa, if you are reading this, I tried. I really tried to be gay. I bought the book. I followed all the steps. I studied. I got all my suits dry cleaned. I even picked out a guy or two. Like a fad diet, it just didn’t stick.

I was also the victim of a girl stopping me during sex to tell me that our entire tryst was a ‘mistake’ that she regretted the moment I started penetrating her. She also added in that she wished she had smoked pot before we made love. It seems there is no end to the indignity, and yet none of these break-ups match the one I went through when I was a mere three years of age.

The female in question will remain nameless, as I have respect for the woman she has become in her late 20s. Without going into detail, I can say she has matured into a spiritually connected, generous, respectful woman. None of those words could be used to describe me, though I can attest to being called a woman on more than one occasion in the last week.

I think I read on Facebook that she does yoga. I could never imagine bending my body like that, unless a bottle of champagne was at the end of the kitchen counter. God bless her for being so truly upstanding. I, on the other hand, am callow, selfish, mired in binges of narcissistic delusion, classist, pretentious and prone to wearing Superman pajamas without underwear while I write. This precocious relationship I had in preschool is clearly the Rosetta Stone of my neuroses. The simple dichotomy of our fates illustrates a painful truth. I was cursed to be miserable before I could even spell the word.

If I were being truly veracious with myself, I would accept that I had no choice but to woo this girl. She had everything a youngster could want in a mate. By the age of two, she had memorized the whole alphabet, minus the vowels. Close enough, it seemed. How often do you need vowels in preschool? Of all the gals on my block, she had the most teeth, which comes in handy more often than not. Her grasp of Chaucer’s Canterbury Tales was unmatched, in that she was the only one in preschool who knew who Chaucer was. In short, she was a prepubescent dream come true.

So that I might add some emotional resonance to this Tennessee Williams melodrama come to life, I shall give a pseudonym to the object of my childish desires. The name “Nancy” seems appropriately bland, like a tube sock fresh out of the dryer. In a way, that’s how I’d like to remember her: comfy, warm and white. Very white.

Nancy’s parents feigned tolerance for our affection. They were not enthusiastic or willing to acknowledge the coupling in public, but they did ferry us to and from activities that were ostensibly referred to as ‘dates.’ Naturally, the standard rules of dating did not apply to children only recently out of diapers. I was not required to pay, there was no imbibing of cocktails, and an erotic period was verboten. What our rendezvouses amounted to were Nancy and I sampling at least 2 of the 31 flavors at Baskin-Robbins while her father stared at me with a mixture of contempt and confusion usually reserved for that time in high school world history class when you have to look at photos of Nazi concentration camps. For me, this was my personal Dachau.

As the days and weeks progressed, I felt as though we were growing closer, despite the silent condemnation from her father. Our conversations become more nuanced. We could jump from the latest episode of Fraggle Rock all the way to the pros and cons of Marxist theory. Ironically, those two subjects often overlapped in surprising ways. I expected Nancy to make the sort of logical leaps her contemporaries could only dream about. Unfortunately, it was during that period that things started to dissolve. As I felt our intellectual discourse becoming more satisfying, our emotional connection severed. She spent more and more time with a boy I will call “Ian.” Ian’s family was far wealthier than mine and had a large pool in their backyard. When deciding between a pool and a Super Soaker, the choice is evident. A Super Soaker can only hold so much water, and a human being can only hold so much love. Nancy left me, told me she didn’t want me talking to her anymore and asked for her Teddy Ruxpin back. I had it on good authority that she never used that Teddy Ruxpin and would just put it in a corner to gather dust. She likely ended up hiding Ecstasy in the tape deck when she moved away to college, but that’s mere speculation on my part.

For Nancy, I assume that our tryst is but a distant memory. She appears to bear no ill effects from our separation. If she does, I can only hope she reads this and informs me of my mistake. Moving on from a brief courtship 24 years ago should be simple. I am here to inform you that it is not. The grand dilemma in all of this is that wooing a woman becomes harder as you get older. It’s not enough that you have a GI Joe Power Wheels and a copy of Aladdin on VHS. Now, you need a good job, a nice apartment, a set of unwavering moral principals and a bank account in the positive. In addition, the trauma of being dumped for a kid whose parents had a swimming pool does not evaporate like so many raindrops. It gets hard, crusty and leaves a dull yellow stain, like the detritus from a night of passionate coupling. You try water, laundry detergent, Spray n’ Wash, bleach, club soda and nothing works. You either buy new sheets or get disgusted looks from your mom when she comes over to visit on Thanksgiving. Plus, you still got dumped by a three-year-old Marxist.

At this juncture in my life, I expect to be dumped when I date. I was at my most guileless, most magnanimous and most honest at three. What chance do I have at 27? If any of my exes are reading this, please find me on Facebook and help me get over this. Nancy, if you are reading this, please forgive me for whatever I did 24 years ago to make you leave me. Did I not stroke your hair enough? Did I not tell you how pretty you were? Did you catch me eating my own boogers? Just grant me absolution from my sins. I would be forever grateful. TC mark

image – Leonid Mamchenkov

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    • http://www.facebook.com/AmustB Anton Bal

      your darkness brings me as much schadenfreude as it reminds me of similar conundrums within myself… aw yeah

    • Erin

      Oh man loved this article.  Funny and yet poignant.

    • http://twitter.com/kathrynmoncada Katie Moncada

      David, that you would take the time to write this in the beautiful manner that you did suggests a high level of introspection.  Never lose that desire so analyze and learn from your past.  I’m sorry that you have been insulted in the ways that you were, but that is not a reflection of yourself, rather the company you chose to keep.  Don’t think if this time as a plateau; realize that it is your chance to find yourself -a process that cannot be done in the company of another.  Best of luck to you in all your endeavors. 

      • http://www.facebook.com/profile.php?id=11705873 David Schilling

        Your sentiments are much appreciated.

    • http://pulse.yahoo.com/_4T27JL52BMUIB55WOG3BZDTTBU Mercedes

      This made me kind of sad but it was a good read, nonetheless.

    • Em

      So adorable! I really liked it.

    • Caloeey

      What a good read. :)

    • Rishtopher

      Very good read. I can relate to getting dumped for a guy whose parents have a pool, so that made me sad, but the rest this made me laugh. Also, my best friend’s name is Nancy, and now I have a hard time disassociating her name with a sock fresh from the dryer lol.

    • MD

      Completely nails it… And THIS coming from a girl whose first genuine relationship didn’t develop until she was a relatively-ancient five… Beautiful work, Mr. Schilling.

    • Anonymous

      ta.gg/5jo

    • Leungkz

      such good writing! probably the most beautifully written thing i have ever read here on thought catalog :) i mean it!

    • http://twitter.com/agentlinden Tyler Woods

      I hate to be that guy but this is the worst fucking piece of shit I have read in a long time. Honestly @ryanoconnell:disqus 
       this should never have been published and I have enough respect for you that I think you know that.God bless her for being so truly upstanding. I, on the other hand, am callow, selfish, mired in binges of narcissistic delusion, classist, pretentious and prone to wearing Superman pajamas without underwear while I write.

      I just read that outloud to myself and remembered Xanga. Never make me go back there again.

      • nerd

        troll

        • http://www.nosexcity.com NoSexCity

          Technically, this is just flaming as he is not anonymous…

      • yo

        that’s just rude..

    • http://www.facebook.com/profile.php?id=831404615 Miranda Edwards

      I tried to like this; I really did. It just didn’t click for me. I do appreciate bits and pieces of this article. Well done, Mr. Schilling, I’m truly sorry I couldn’t relate. I’ll be looking forward to the next things you write. 

    • rooar

      cute piece, so sad yet so cute

    • dip

      “I was also the victim of a girl stopping me during sex to tell me that our entire tryst was a ‘mistake’ that she regretted the moment I started penetrating her. She also added in that she wished she had smoked pot before we made love.”

      this one sounds like a keeper, what were you thinking?

      • http://www.nosexcity.com NoSexCity

        At first I was like “oh god, did I just get zinged?” but then realized I have not slept with Dave Schiller. (Just variations thereof.)

    • http://twitter.com/danmckean Dan Mckean-Tinker

      This makes my dating mishaps feel tame and petty. For that diminishing effect and the wonderful way in which it’s written, I loved it.

    • Allyson

      I’m in love.

    • http://pulse.yahoo.com/_VYDVROKY4PUBOKUHB3QF42FH2Y Paul S

      Not sure how serious you are about hitting your
      “peak/plateau” (you kids and your silly “irony/sarcasm”), but take it from
      someone that just turned 40, it gets better. A LOT better! Sure, you gotta work
      a little harder to stay in shape, but everything else comes easier, regardless
      of if you’re married or not. If you want it, you can be swimming in young
      20-something poon, much more than when you were 20-something
      yourself.

    • http://michaelynch.com Michael Lynch

      Your most prized relationship was when you were a toddler. Am I the only one that sees something weird about this?

      • http://www.facebook.com/profile.php?id=11705873 David Schilling

        No. I do too.

    • Geoffrey [Chaucer]

      Is this a satire,  or are you honestly claiming that you and “your first girlfriend” discussed Marxism as toddlers?

      Because that is both unimaginable and pretentious.

      • Natalie

        Seriously? Actually though? You must be joking.

    • Keltydennis

      Funny, when i was three I broke up with my “boyfriend” because he stepped on a bee and started crying. I did not see him as being man enough to handle me.

    • Anonymous

      phlpn.es/7x9vmd

    • Benjy

      When I was in kindergarten I kissed a girl named Amanda on the bus ride to school. We didn’t quite grasp the concept of making out so it was just repeated pecks. Young love, so cute it makes  me throw up a little.

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