How to Save a Conversation

The pauses were excruciating. My parents and I stared across the room at my chemistry teacher and his wife. We smiled with northern white Protestant smiles. We had nothing to say. I swore that when I grew up, I would never settle for an awkward conversation.

I was completely wrong. Only the rude and aggressive can fly through life without engaging in the occasional awkward chatter. I learned three ways to revive a dying conversation when you can’t just walk away.

To ask questions

I’m friends with the podcast host you’ve heard of. He makes his living interviewing people, including people who seem boring at first. But he always finds something to do. He is the same in real life: no matter what you say, he listens carefully, notices any hint of something interesting and asks about it.

You can’t just use this trick or your conversation will start to resemble a job interview. I was trapped in several conversations in which I was constantly answering questions, and the other person did not give me any material to ask them something in return. In between questions, you should:

Give longer answers than strictly necessary

A new question moves the conversation forward. Adding your own thoughts allows the conversation to breathe. Follow someone else’s answer with your own, or point out where you agree or (good-naturedly) disagree. Find a little tangent to continue.

A common mistake is just a literal answer to the question: “Where are you from?” “Rochester, State Province.” You are not filling out a form, you are having a conversation, so do it. “Actually a tiny town south of Rochester with one street lamp. Lima is called, like beans. They had a lima bean festival! “

You can answer differently each time. I don’t want to talk about beans in every conversation. Sometimes I mention a bar in my hometown called “the largest urinal in the world”, sometimes I talk about my tiny K-12 Baptist school, sometimes my favorite coffee shops in Rochester, sometimes my neighbors were a former one-room school building and a cornfield.

Or I move on to talking about San Francisco, where I lived for three years of founding, and I miss it desperately. It didn’t hurt anyone that I didn’t stick to a strict answer, because we weren’t in the courtroom, but in a bad surf bar in Hell’s Kitchen.

Get ready to turn

In fact, I completely smelled the conversation at that surf bar just last week. Four of us talked about New York City neighborhoods and how each one is ennobled. We will think about the area, name a couple of changes in it, agree that the city as a whole is improving, and repeat. This is a normal conversation in New York, and we soon ran out of steam. We forgot to prepare the turn.

A twist is a change of topic. It’s not a jump — a new topic suddenly came up. Sometimes jumping is okay, but with people you don’t know well, it can highlight your desperation to find a new topic. Better to move away from something mentioned earlier.

This is where long question answers really pay off. If someone uses more than two sentences, you should set aside some details so that you can ask more about them later, or use them as an excuse to tell a new story outside the current conversation. This is why I love moving from Lima and Rochester to the more famous San Francisco, where there are a million things to share. (Or talk about gentrification again.)

Better to rely on what someone else has said, not your own. I have a bad habit of speaking monologues, getting distracted, and then picking up various digressions. If you only get distracted from what you raised yourself, even if you give the other person the opportunity to talk, you can still control the direction of the conversation too tightly. So when you want to turn, see if you can turn selflessly.

Always remember: everyone has something to be interesting. Small talk is tiresome until you find this thing.


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