How do you view this word?
Is it a delinquent that breaks in uninvited during adolescence and deserves to be locked up for life with no chance of probation? Or perhaps more like an irritating second cousin, predictably showing up and causing mild discomfort at weddings and funerals.
My automatic association with the word awkward is a memory. The funny thing about memory is how our brain archives and even deletes objectively significant names, places and events. At the same time it permanently imprints the smallest possible interactions with surgical precision.
It was late summer 2011. I was working as a full time cabin leader on a camp located in a tiny coastal town in Nova Scotia. Summers at camp felt like stumbling into the very best kind of parallel universe imaginable. We would swim in the ocean, sing our hearts out in the little wooden chapel and eat cheesy pasta like we were on death row.
On this specific evening, I had lost track of time. To be honest, I was a little distracted all day. One of my campers had a big brother who was a well known folk musician, and rumor had it that he might make an appearance at some point. Anyways, I only had about ten minutes to figure out how to embody an icon from the 1980s for our theme dinner. I was leaning down, desperately rummaging through the tickle trunk (a solid wooden chest filled with dress-up clothes), when in my periphery I saw a tall figure with a man bun and a plaid shirt. I instantly lost every bit of cool. As my head jerked up, the heavy lid of the trunk crashed down. The impact was direct and solid.
It’s funny how time moves into slow-motion when you desperately need it to fast-forward. I can still hear that deep, familiar, beautiful voice: “Oof, looks like that might have hurt.” I can still feel my whole being shift from shock to utter mortification. And I still see myself standing speechless in front of him, desperately wishing I could trade the neon purple dress in my hands for a shred of dignity.
Coined somewhere in Scotland during the Middle Ages, awkward literally means “turned in the wrong direction.” Some of its nearest relatives include inconvenient, clumsy, and uncomfortable. Why wouldn’t we make every effort to annihilate a word that is, right down to its spelling and pronunciation, well.. awkward? In fact, sometimes I wonder if the creators of AI are on a personal mission to erase it entirely from the 13th edition of Webster’s Dictionary.
Imagine your grandma waking up one morning in the 1930s, and deciding that she must learn everything there is to know about the pufferfish. The process would have likely been quite awkward. She might have peppered her friends, family, and teachers with questions, and then found herself sorting through a variety of facts, anecdotes, and outright fictions. If she was still curious, grandma might then have walked a kilometer to the local library. After sorting through books about animals and flipping through chapters about whales and jellyfish, she might have found two paragraphs on page 256 accompanied by a pixilated photo of a porcupine pufferfish.
Now imagine grandma two years later. While lounging on a beach, she suddenly spots a dead spotted pufferfish. Her mind drifts back to her fleeting obsession. She chuckles as she recalls the moment her great uncle used the pufferfish as a segway to reminisce about his adventures as a sailor. She can still see the veiled disdain in her sister’s eyes as she remarked that these kind of questions would never land her a boyfriend. She can feel the hot sun beating in her head as she doggedly trudged to the library. And as she relives every awkward moment, she suddenly remembers that pufferfish are 1000 times more poisonous than cyanide. And that dolphins sometimes irritate them intentionally so that they can get high off the toxins.
What would have happened if grandma had a time-travel device and was able to use chatGTP to avoid all the awkwardness? What if she simply rolled over, picked up a smart phone from her night table and pulled up an AI summary with ten times the information she could have ever hoped to access the hard way? Would she have recalled anything at all two years later? I suppose only a true time-traveler can definitively tell us the answer.
As far as I know, my real grandma did not give a fig about pufferfish. But she did care deeply about something that touches the heart of every human on this planet. Forming meaningful, lasting, human relationships. And this is arguably the most awkward process in the history of the world. A soul-level friendship is often built on a mosaic of uncomfortable moments and wrong turns. Gut-level apprehension when two strangers have absolutely no shared experience. Painful embarrassment when a joke lands badly. Grating irritation when the rough edges of two personalities meet. Deep hurt when old wounds get exposed.
Over the past while, my young clients have given me a sort of crash course on ways to avoid relational awkwardness. If things become uncomfortable in person, pull out a smart phone and pretend you just received an important message. To minimize the risk of this happening in the first place, try to make all vulnerable disclosures online. If you get a text message from your high school crush, leave it marked “unread” for long enough to get AI to thoroughly analyze it for undercurrents of flirtation. Get AI to suggest a list of five appropriately witty replies.
What happens when we remove awkwardness from the process of building knowledge, and relationships? Is it merely scrap metal to be discarded in the name of progress? Or could it possibly be a foundational piece that holds important memories, meaning, and emotions?
I can still relive every little drop of awkwardness from the tickle trunk situation. But the funny thing is, I also remember the feeling of damp, salty hair and sandy toes from my afternoon swim in the ocean. I can still hear Cindy Lauper’s voice belting through the loudspeaker during our fabulous 80s-themed dinner. And to this day, I get a silly smile on my face when a song by that folk singer comes on my Spotify mix. And I would absolutely not trade any of that to erase a few moments of awkwardness.

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