How to Make Any Conversation Awkward

for Sarah

For reasons which will soon become apparent, I don't remember the entire incident leading up to the suggestion that I write this blog post, but I do remember where I was at the time. 

Last week, as I stood chatting with two work colleagues in their shared classroom, I came to the realization that our conversation had suddenly lapsed. I feared somewhat belatedly that I'd been daydreaming, and I realized that I had no idea how long the silence had stretched.

Oops. Was I supposed to be saying something?

"You know," one of my work friends began, sitting on the side of her desk while scratching her head with coat hanger, "you should really write a blog--"

"Oh, I do!"

"--post about awkward conversations."

I blinked at her. "You're absolutely right."

After all, writers are often encouraged to write what they know best.

And if there's one concept that I seem to know intimately, it's the concept of awkward.

How to Make Any Conversation Awkward:

1. Practice excessive eye contact.  Eye contact is important.  It's a sign of honesty and integrity.  When done correctly, it's a way to tell people that we are interested in what they have to say. When  done incorrectly, it's a way to give people the impression that we would like nothing better than to use the severity of our gaze to bore holes directly through their skulls and flip through all of their thoughts as we would through the pages of a Filofax. 

I wish.

Apparently this is something that I have been guilty of more often than I have been aware. Increasingly, though, it has been something that I've practiced intentionally. 

My unintentional staring generally occurs during moments of great concentration.  When someone is talking about something that interests me (such as a gruesome true crime) or something that I'm working hard to understand, but am worried that I never will (such as anything relating to science and industry),  I attempt to make up for what I lack in understanding with sheer force of concentration. More than a few people have found this unnerving.  

One middle-aged salesman from whom I bought a cell phone actually commented that he was having trouble concentrating because I made him feel so nervous.

"I do?" I was genuinely surprised.

"You just keep staring at me like that," he actually rubbed his eyes, "and you've got me worried I'm going to say something wrong."

It's been obvious to me for some time that a certain percentage of students find maintaining eye contact with me to be excruciating.  Sometimes I'm not sure why.  Sometimes I am. 

Sometimes I just stare at people until they say something.  Anything.

Instant awkward!

Variation: If you find that staring directly into people's souls doesn't work for you, try staring just a few centimeters above someone's right eyebrow during the course of an entire conversation. If he shifts his stance to accommodate your off-kilter stare, shift to match.

2. Incorporate everything you have gleaned about someone through interaction on social media into your realtime conversations. This one is self-explanatory, but it's done best when it's delivered sotto voce to a third party.  On a recent trip to Chicago, I was enjoying getting to know my new friend *Whitney. Her husband, *Jim, who has kept up with me for some time via the internet, would punctuate my narrative with helpful explanatory nuggets, all of them gleaned through things that I've posted on social media.  

At one point, Whitney stopped him.  "It's creepy how he does that, right?"

"It is, a little," I concurred.

"Anything you've ever Tweeted, he'll remember," her eyes glowed with affection.

Honestly, I did not find Jim's few instances of this to be awkward, but I've met other people who can't seem to hold themselves back from prosing on about social media during realtime conversations. There's a definite line between allowing references to the internet to pepper one's conversation and allowing it to become the actual source of and sole topic of conversation.  Nothing feels more awkward than the heartlessly truncated conversations that go something like this:

Person 1: So, I'm reading this book called--

Person 2: Revenge of the Vampire Prom Queens. Yeah, I saw on Facebook that you'd added that to your Goodreads shelf.

Person 1: Yeah! And I really liked it--

Person 2: Obviously! Because you gave it five stars--

Person 1 (faint, but pursuing): --because of its satirical overtones--

Person 2: "--which actually help to infuse new life into the otherwise tired literary tropes." Yeah, I saw that you posted that.

Person 1: Yeah. Um, I was thinking next of reading Vampire Prom Queens IV: The BloodDrive--

Person 2: Oh, yeah! I saw that on your "to read" list!

Person 1: Yeah... so.  Um. Yeah.

Person 2: Yeah.

And on like that.

Variation: Even when you know very well that what your friend has to say is news to you, pretend that you've already seen it posted somewhere. When he says that's impossible, spend the next ten minutes scrolling through pages on your smartphone, allowing the possibility of proving him wrong to eclipse the import of your original conversation. Instant awkward.

3. Take everything personally.  I learned this one from years of teaching middle school girls.  Awkward squared. Possibly to the third power. 

4. Refuse to pick up the thread of conversation offered to you.  Blissfully ignoring your friend's attempt at linear conversation, you must be sure that the comments you make don't quite square with what has just been said.  When done correctly, having conversations like these leaves others feeling as if they've been doing the verbal equivalent of riding a square-wheeled bicycle: it's a lot of fits and starts, and it's just about impossible to get any momentum going. 

Variation: Find a favorite topic and refuse to budge from it. No matter what conversational paths your friend tries to lead you down, do your utmost to ensure that the conversation leads back to your primary topic for the night.  Choose something inane, like a wheat germ. Or your third-grade spelling bee. Or a Lifetime Original movie. Or recycling. Or a Nicholas Sparks book. 

The truth is that most of us don't need any tips regarding how to make our conversations more awkward.  If you're anything like me, you seem to have that covered all on your own. What many of us really need instead are some pointers on how to make our conversations more meaningful.  

You may find it helpful to bear these in mind:
1. Do everything that you can to make the conversation about the other person instead of yourself. In this respect, asking lots of good questions is pivotal.
2. Listen more and talk less.
3. Remember what people say and incorporate it into conversation(s) later.
4. Never pass up an opportunity to say a kind word or give a sincere compliment.

*Not their real names.


  1. HA! I am sure I do the whole staring just a few centimeters above someone's right eyebrow awkwardness. I don't mean to but looking into someone's eyes the whole convo makes ME feel awkward. :)

    1. It does? I don't remember your being weird about eye contact. And I would know, too, because of all the staring people in the face that I do when I'm around people (especially when I'm interested in what they have to say, just as I was interested in every pearl of wisdom that dribbled from your lips).


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