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Digital Love or Connection Lost? by Kailyn Bennett

Digital Love or Connection Lost? by Kailyn Bennett

“What are your hobbies?” I asked. Two tequila shots and a cocktail that was in an egg shaped glass later. My foggy mind couldn’t conjure up any better question for a first date besides the standard. “When I lived in the northwest we threw a giant log into the water, drank some beers, and tried to see who could hit it with a rock.”


I hate dating, mostly because I don’t know how to pick ‘em. I always seem to go out with the dumb-dumbs of the earth or choose a partner who is emotionally unavailable or WAY too available. I can’t get through these horror shows, without a good ol’ dose of American medication: booze.


This past year, the amount of men interested in me has risen exponentially. When I moved to Chicago, I dropped twenty pounds from leading a healthier lifestyle and allowing myself to let go of emotional baggage. I focused on healthy eating, self-acceptance, and found myself through walks on the slathered concrete and long writing sessions with my guitar. My face slimed, my pale collarbones emerged, and my ribs became visible as a curve appeared from my torso to my hips revealing my womanly form.


The problem is that I’m no champion at dating. From flings to one-night stands to accidental celibacy, I have not mastered how to find and keep love in my life. My belief has been that a partner is elusive, unfulfilling, and honestly a time-suck.


Part of my problem with modern dating is the technological element that is so ingrained in the act. We sit in the dark corners of our comfort zone, swiping left and right, judging meaningless photos to see if a person could be a potential mate—as if two sentences and a photo could determine that.


With the boom in social media, gaze has become the basis for attraction and ultimately connection, while initial touch is neglected. We romanticize images that are carefully selected, cropped, and edited, and to us these are people rather than representations. I don’t need to consult a science book to say that, when you are interested in someone and you touch him or her or they touch you, an internal Fourth of July occurs. You want to “Julie Andrews” it on a hill and scream at a high pitch. However, we utilize the gaze and touch our alien-like light up screens. Or we watch porn, internet chat (often with robots), eat an abundance of junk food or consume liquor to numb ourselves and call it good: connection made. But in reality, connection lost.


I was not confounded by this trend of Internet connection until I received an Internet love letter several months ago.


I would like to tell you as honest as I can, I genuinely have a big cuddly, ear to ear, googly eyed crush on you. We live in different worlds and have only met once, but when I think about a person, male or female, I would love to bring happiness to, you come to mind. And I can absolutely understand if this comes off as very forward, or if you don't remember me, I will not take you not messaging me back as an insult.

Sincerely (Man’s Name)

P.S. If I could I would have hand wrote this in a letter. I prefer to be more romantic if possible.”

I have to admit this letter struck me. My face grew red, my heart palpitated, and I began to get weird and sweaty--I was bewildered. This letter was vulnerable, genuine, and bold, but how could someone feel a connection when they had only met me once? He does not know about the scar on my elbow or have heard my laugh that is often too loud. He has not seen the development of laugh lines that compliment my dimple on my right cheek or touched the abundance of freckles that cascade down my ivory skin. To him, I am pictures. Short sentences that I choose to publicize online. These create a fragmented, foggy image of the fully fleshed human I have turned out to be.

The question that has puzzled my mind is: why? Why is it that our society is prioritizing this form of connection over something organic? The initial answers brought to my mind were convenience—our society is “fast food” based in the sense that we go, go, go and need our lives to be on the go too. We can fly from Hong Kong to Chicago in as little as fifteen hours—we don’t always have the time or luxury to woo the man or woman at the grocery store. I also considered access. Social media connection has given us a method to access people we may not have met otherwise. I think one of the reasons may be a bit deeper than that though.

I think back to my Tinder dating resume—two dates in all. One was with a DJ in Colorado who was short and smelled of BO and still wore skater shoes although he was 30--he did take me to the art museum and that was impressive. The second was when I first moved to Chicago, and I went out with a wanna-be Ryan Adams style musician who over sold himself by taking artsy photos; he was more awkward than a fish trying to climb a tree. My major take away from these experiences was that they were not what I expected, and I was not what they expected. The DJ said, “In your pictures you were smoldering. In real life, you’re just so sweet.”

This style of dating is a mechanism for perfection. Shaped abs and long legs have been rammed down our throats through the media, and we can have some control of how the others view us with the images we post. I certainly know that I am guilty of posting images that show me in my best light—not in the gym shorts, old band t-shirt with a hole in the armpit, and ratty hair that I’m currently sporting all wrapped up like a goblin in my poncho.

By connecting on social media, I’ve noticed that it lessens the blow of expectations and rejection. If someone is not interested on Tinder, you will not match with him or her, which is less of a punch to one’s pride than getting turned down in the wild.

I turned to this form of dating because I was scared. To approach the precipice of asking someone out raw is a terrifying act. What if they think I’m not pretty enough? Clever enough? What if I don’t dress like X, Y, or Z? What if I say something stupid? What if I do something stupider?

As a society we have become so afraid of rejection that we hide behind the letters of a keyboard and romanticize images of perfection. In reality, we all have darkness, imperfections, secrets, and tales of the abyss—those are the qualities that make us interesting and desirable. Many of us try to hide them because we care about initial acceptance over connection.

A couple of years ago at a bar in Colorado, I was not ready to go home. I sat by myself, drinking my signature drink, a tequila soda, watching the date night’s kiss, the drunks lean, and the moon rise. A man approached. He was tall with dark eyes and a paisley pocket square.  “Hi, I knew that I just needed to talk to you.” This connection felt like lightning in a bottle. Now, it didn’t work out how we all hoped with a long, lasting romance, however it was one of my favorite instances. This man was traveling, so we only spent a couple of nights talking about our mutual love for Bob Dylan and how we enjoy pranking people, but how we met always left an imprint on me.

I don’t have the keys to modern dating and how to craft a connection. It works differently for everyone. I know people who have had immense success with internet dating and now have a baby and white picket fence. I know folks that have met in line at a comedy theater or people who had a “When Harry Met Sally” style affair. The important thing is that we try. We put down our cellular devices and make connections in a connectionless world. We look up and see that human drinking alone and say, “Hello.”



Kailyn is a budding musician and writer. She is currently based in Chicago but hails from Colorado. Kailyn enjoys vintage shopping, yoga, watercoloring, and ogling at motorcycles. Look for her artistic work in the near future. 

Kailyn is a budding musician and writer. She is currently based in Chicago but hails from Colorado. Kailyn enjoys vintage shopping, yoga, watercoloring, and ogling at motorcycles. Look for her artistic work in the near future. 

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