Why We Expect Awkwardness - and Why We’re Usually Wrong
There’s a line I heard repeatedly at our last event: “I almost didn’t come. I thought it would be awkward.”
I get it. Talking to new people as an adult feels difficult. Most of us assume any conversation with strangers that goes beyond “Nice weather we’re having” will be uncomfortable, maybe even embarrassing. So we stay in the safer lane - the weather, the job, the same five surface-level exchanges we’ve all memorized and can run through without any thought at all.
Recently I read a study that put the reality of this perception to the test. Researchers set out to answer:
“Are we avoiding deeper conversations because they actually feel bad, or because we’re predicting they’ll feel bad?”
Researchers paired strangers and asked half of them to talk about light topics (TV shows, favorite foods), and the other half to answer deeper questions (real memories, personal insights). Before the conversations, everyone guessed what it would feel like., and people predicted the deeper conversations would be uncomfortable and awkward.
Then they actually had the conversations.
And here’s the twist:
The deeper conversations felt better, more enjoyable, more connecting, more human, and far less awkward than anyone expected. People even cared more about what the other person shared than the speaker assumed they would.
So the big takeaway is this:
We avoid the very conversations that make us feel good because we’re terrible at predicting how good they’ll feel.
That misprediction doesn’t happen in a vacuum. It shows up now more than ever because the world gives us fewer chances to find out these assumptions are wrong. We spend more time online, more time at home, more time in spaces where the only conversations available are shallow by default. When life pushes us toward isolation and distraction, anything unscripted starts to feel risky. So we assume connection will be awkward, we avoid it, and then the cycle reinforces itself.
New Haven IRL is built to to give people the opportunity to have meaningful and interesting conversations with strangers in a safe way. Our prompts provide the framework to skip talking about the weather and get to a deeper level more quickly.
We’re not trying to “teach conversation” or to force vulnerability, but instead to create the conditions where people can move past that wrong prediction and the risk we associate with it. We worry it’ll be awkward, but it rarely is. We assume nobody wants to hear what we have to say, but they usually do. When you put adults in the right room, with smart pacing, warm atmosphere, and a thoughtful prompt to start from, something opens up. Conversations move past the scripted stuff and into the place where things get more interesting and fun.
The study just confirmed what I see every time I host one of these nights: people are more interesting, more generous, and more open than we expect. Sometimes we just need a structure that gives us permission to enjoy it.
That’s the whole idea behind IRL. It’s a place where it becomes easier to talk to each other in the ways we’ve been wanting to.
And every time the room fills and people start leaning in, laughing, telling stories they didn’t plan to tell, I’m reminded - the awkwardness we worry about is almost never the reality.
We just needed to create a space that proves it.
-Jesse Giorgio, Founder of New Haven IRL
Kardas, M., Kumar, A., & Epley, N. (2022). Overly shallow? Miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology, 122(3), 399–421. https://doi.org/10.1037/pspa0000281