How To Keep A Conversation Flowing

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

I was entirely wrong. Only the rude and the aggressive can blow through life without tripping into the occasional halting, awkward chat. I’ve learned three ways to revive a dying conversation when you can’t just leave.

Ask questions

I’m friends with a podcast host you’ve heard of. He interviews people for a living, including people who at first seem boring. But he always finds something interesting to pursue. He’s like that in real life too: Whatever you’re saying, he listens intently, notices any hint of something interesting, and asks about it.

You can’t only use this trick, or else your conversation will start to feel like an interview. I’ve been trapped in a few conversations where I was constantly answering questions, and the other person didn’t give me any material to ask them something back. Between your questions, you’ve got to:

Give longer answers than strictly necessary

Asking a new question drives a conversation forward. Adding your own thoughts lets the conversation breathe. Follow someone’s answer with your own, or point out where you agree or (genially) disagree. Find a bit of a tangent to go on.

A common mistake is only giving the literal answer to a question: “Where are you from?” “Rochester, upstate.” You’re not filling out a form, you’re making conversation, so make it. “Actually a tiny town south of Rochester with one street light. Called Lima, like the bean. They had a lima bean festival!”

You can answer a different way every time. I don’t want to talk about lima beans in every conversation. Sometimes I mention the hometown bar that claims “the world’s biggest urinal,” sometimes I talk about my tiny K-12 Baptist school, sometimes my favourite coffeeshops in Rochester, sometimes how my neighbours were a former one-room schoolhouse and a corn field.

Or I pivot to talking about San Francisco, where I lived for three formative years and miss fiercely. No one’s offended that I didn’t stick to the strict answer, because we’re not in a courtroom, we’re in a bad surf bar in Hell’s Kitchen.

Get ready to pivot

Actually, I totally whiffed the conversation in that surf bar, just last week. Four of us were talking about New York neighbourhoods, and how each one has gentrified. We’d think of a neighbourhood, name a couple changes in it, agree that the city is gentrifying as a whole, and repeat. It’s a common conversation in New York, and soon we ran out of steam. We forgot to prepare a pivot.

A pivot is a change of topic. It isn’t a leap — coming up with a new subject out of the blue. A leap is fine sometimes, but with people you don’t know well, it can highlight your desperation to find a new topic. It’s better to branch off of something someone previously mentioned.

That’s where long answers to questions really pay off. If someone’s going on for more than two sentences, you should be pocketing some detail to ask more about later, or to use as an excuse to tell a new story, outside the current scope of the conversation. That’s why I like to pivot from Lima and Rochester to the more famous San Francisco, where there are a million things I could go on about. (Or have yet another chat about gentrification.)

It’s better to pivot off what someone else said, rather than your own. I have a bad habit of monologuing, digressing, then picking up my various digressions. If you only pivot from things you brought up yourself, even if you give the other person a chance to talk, you can still end up too tightly controlling the direction of the conversation. So when you’re looking to pivot, see if you can pivot selflessly.

Always remember: Everyone has something they can be interesting about. Small talk is only boring until you find that thing.


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