Question:
I have this really strange dynamic with this person I kind-of know…
We met once at an event and had a whole conversation, but haven’t really talked since, and, for no reason whatsoever, it’s just gotten so weird...
He so clearly avoids eye contact with me when we’re in the same place.
Honestly, I do the same with him…the awkwardness is killing me…What can I do???
Advice from the Sages:
Awkwardness is one of the silent scourges of modern society.
The word “awkward” has quadrupled in usage since the 1970s. Millennials use it to describe everyday scenarios more often than their Gen X predecessors, and Gen Z even more than Millennials.
The world is apparently an ever increasingly awkward place, but why???

I’d like to suggest that growing passivity is the source of the growing awkwardness.
When people are waiting for the other person to fix their relationship or lack thereof, the relationship doesn’t get fixed. What results is that the awkwardness deepens because both parties are thinking to themselves, “Why aren’t you doing anything about the fact that it’s weird between us?” The more awkward it gets, the more both sides avoid engaging with one another, and thus awkwardness is augmented.
Why do so many of us assume such passive postures in the first place?
The applications of the core idea here are vast, but let’s take the simple scenario from your question:
You met someone informally at an event. It was quick and casual and forgot his name, as often happens. Now, you find yourself in a Larry-David-esque situation of ducking and dodging him so that you don’t get into an awkward situation in which you’re “caught” not knowing his name, which might make you look like you didn’t care to remember his name when he first introduced himself (which may be true). The problem is that in avoiding this fleeting awkwardness and judgment, you’ve introduced a new extended awkwardness of avoiding eye contact with him indefinitely. The longer you wait to say, “I’m so sorry, but I’m embarrassed to say that I forgot your name. Can you please remind me?” the stranger it is that you waited so long — thereby perpetuating the very same problem you are trying to avoid: the problem of looking like a person who doesn’t care about other people.
If it makes no sense, why do so many people behave this way?
The root cause of awkward relationships is people’s lack of belief in themselves. You are afraid of this person’s judgment of you in admitting that you spaced out on his name, thinking that you’ll never recuperate from such a devastating blow to his perception of you. But again, consider that his perception of you will not improve by you avoiding him.
Here’s the good news: you’re clearly a person who wants to have good relationships with other people. You want peace and harmony. This is the critical motivation you need to improve your dynamic with this person, and with others in your life as well.
I recommend experimenting with the advice from Rebbi Matya Ben Charash (2nd century CE, Judaea and Rome) that is so simple, yet life-changing if implemented.
In the wake of destruction wrought by the Roman legions on Judaea in 135 CE, Rav Matya set out for Rome to establish a school and court of law. It was widely understood that the Jewish society physically destroyed by the Romans was first socially destroyed by the Jews themselves through cliques that didn’t speak to one another. Rav Matya boiled down the lessons he had learned by living through this into a few simple words that he hoped would rebuild a better Jewish community after the dust settled:
Don’t wait for the other person to stop being awkward. If you crave normalcy, harmony, and relationship — do something about it.
In the words of King David:
You be the one to get over the hump of awkwardness. I would tell you to take the risk of rejection, but truthfully, it’s not much of a risk. It’s much more likely that you’ll be respected and thanked for making the first gesture than be judged for it.
Ultimately, peace is established by those who genuinely seek peace, harmony and integrity within themselves, which you clearly do.
Now, you have to “run after it.”
There are many more people out there who would respond to the greetings of others than there are people who actually initiate those greetings in the first place. Become the kind of person who makes the world go around by developing the habit of saying “hello” instead of waiting for the “hello” of others.
Awkwardness sounds like a joke, but it runs deep. Awkwardness is ultimately about estrangement between people who could have a connection if one of them were willing to cross the chasm. The people who make these move are the people who make our world friendlier, kinder, more whole, and less awkward — one greeting at a time.
Rav Matya’s teaching continues with the famous line, “[Better that you] be the tail to lions, than the head to foxes.” A person with who has real self-esteem is able to say hello to people without fear of their judgment. So too, a person with real self-esteem would rather be part of something great, even if their role is small, than be considered a really important figure that is leading something of actual insignificance.