Conversation · Small talk and flow
How to not be boring in conversation
Being boring is rarely about your life and mostly about how it comes out: summary words like "crazy" and "so good" that give people nothing to picture, and a tour of backstory before the moment. Swap the summary for one or two concrete details: an object, a number, a sound. Open from inside the moment, add one sentence of backstory after it, and stop on the line that holds the feeling.
Why do my stories fall flat?
Usually in one of two places.
Your neighbor, raking leaves in the next yard, asks how the Grand Canyon trip was. You say, "Oh, it was amazing. Honestly, so beautiful, kind of crazy. Really good." He says "Nice" and goes back to his rake. Amazing, crazy, intense, so good: these are summaries. They tell people how to feel and give them nothing to see, and what they can't see, they can't ask about.
Or you go the other way and start at the start: "So we left on Thursday, no, Friday, because my sister had work, and her husband drove the first part, and we stopped in Albuquerque…" There may be a good story in there, but it's still in New Mexico, and your neighbor has raked half his yard.
The short form of the same thing is "Fine," "Not much," "It was good": a summary with the story taken out. Holding back feels likable, and that's a misread. In one set of studies, people predicted they'd be liked more if they talked less than half the time with a stranger, but when researchers assigned people to talk anywhere from 30 to 70 percent of a conversation, the more they talked, the more they were liked (Hirschi, Wilson & Gilbert, 2022). You don't have to hold the floor. Just give the short answer one thing in it: "Fine. I finally got the drawer by the stove to close."
How do you tell a story people actually want to hear?
Give them one or two concrete details: an object, a number, a sound. Not the most accurate ones, the ones that hold the feeling. Name the feeling first, to yourself: a laugh, dread, relief. Then ask which thing carried it.
The canyon story's feeling was a laugh, and the thing that carried it was small: "We drove eleven hours, and my niece looked at the Grand Canyon for about four seconds and asked if the motel had a waffle machine." Now your neighbor can see it, and he has something to ask.
Your instinct pulls the other way. In a lab study, people who retold a story to entertain put more feeling into it and fewer sensory details than people who retold it accurately (Dudukovic, Marsh & Tversky, 2004). Trying to be interesting is exactly when "it was insane" creeps in. Swap each adjective for the thing that made you use it: "scary" becomes "the gas light on, forty miles to the next town."
Where it goes wrong:
- Five details instead of two. Two are a picture; five are an inventory. The rest are answers if they ask.
- A detail that fights the feeling. In the story of a scare, the funniest thing about that night turns it into a different story. Save it for another one.
- Describing what they already know. If they know the place as well as you do, skip the place and give them the moment: what was in your hands, what you heard.
- Making it up. If you're not sure, say it as you have it: "a blue sedan, I think." An honest "I think" still gives them a picture; an invented detail becomes the memory.
Where should a story start?
Inside the moment. Your first sentence is already in the part the story is about: the niece and the waffle machine. Not the day, the weather, how you got there or who everyone is.
Keep only what the story can't be understood without, and say it in one sentence after the opening line, not before it: "We'd driven eleven hours for that." They'll ask for anything else, and those questions are easy:
- "Wait, how old is she?" Answer in a few words, "seven," and carry on. They asked for one fact, not a restart.
- "Wait, who?" When someone new comes into the story, one line is enough to picture them: "my sister's husband, the one who won't use GPS." His job and hometown only delay the good part.
Not sure where the moment is? Ask yourself what you'd say if you had one sentence, and open with that. Tell it in order only when the order is the point: a doctor or an insurer asking what happened, or someone who needs the way there.
A scene to try
By the mailboxes in your building's lobby, Marisol from the apartment below asks what happened on Saturday night: she heard your smoke alarm through the ceiling. In order, it went like this: you had six people over for dinner, you tried broiling salmon for the first time, the kitchen filled with smoke, and your coworker's husband, the tallest guest, stood on a chair and fanned the alarm with a cutting board. What do you say?
One way to handle it
"My coworker's husband was standing on my kitchen chair, fanning the smoke alarm with a cutting board. I'd tried to broil salmon for six."
Why it works
- The first sentence is already inside the moment. The invitation and the recipe can wait.
- The backstory gets one sentence, after the opening line, because the smoke makes no sense without the salmon.
- A cutting board and a man on a chair are things she can see. "It was a total disaster" would have given her nothing to ask about.
In the app, the lesson "Start Near the End" ends with a scene like this one: you type or say your own line, and the AI tells you what landed and what to change.
What if my life just isn't that interesting?
You don't need a canyon. Most good stories at a kitchen table are small moments from an ordinary day with one detail in them: "The self-checkout called for help three times while I was buying one lime." Everyone has stood at that machine, which is exactly why it works.
In a series of experiments, both tellers and listeners predicted that listeners would enjoy hearing about experiences new to them more. In fact, listeners enjoyed hearing about experiences they'd had themselves much more, because speech is full of gaps, and a familiar story lets the listener fill them from their own life (Cooney, Gilbert & Wilson, 2017). The authors also point out that stories about new experiences are harder to tell than people expect. So a big trip told in summary words loses twice: the listener can't fill the gaps, and you've left nothing in them.
Where to find them: the thing you texted a friend about this week, the moment something didn't go as planned, the line a stranger said that you repeated at home.
How do I end a story without rambling?
Stop on the line that holds the feeling. For the canyon: "Eleven hours in the car, and the waffle machine got the better review." Say it, and stop. Then hand the floor over: a pause, or one light question about the story, "Have you ever driven a long way for something that flopped?"
The boring version keeps going after the laugh: the motel, the drive back, what you'd pack next time. Each extra sentence takes a little of the laugh back.
A story is told by two people. When people told a stranger about a close call of their own, the listeners' winces and exclamations tracked what the teller was saying, and when researchers distracted the listeners, the tellers told their stories noticeably worse, especially at what should have been the dramatic ending (Bavelas, Coates & Johnson, 2000). Your listener is half the story, and the ending is where that shows most.
After the last line, resist two things:
- Filling the quiet. A short silence is them taking it in. If nobody speaks, ask your question; don't add the drive home.
- Topping their story. If they answer with one of their own, hear it to the end, even the slow part. "Oh, that reminds me" turns a shared moment into a scoreboard.
Try it today
Two reps, with whoever you talk to today.
- In the next story you tell, swap one summary word for the thing behind it: an object, a number or a sound. Afterward, note what they asked about.
- In one story today, open from inside the moment, with one sentence of backstory at most. Stop on the line that gets the laugh or the nod, ask one question about it, and hear their answer out.
Practice this in the app
Storytelling
Three lessons on exactly this, "The Detail That Does the Work", "Start Near the End" and "Land It, Then Hand It Over": the one or two concrete details that let people see the moment, the first line that starts inside it, and the last line you stop on before you hand the floor over. Each ends with a scene you answer in your own words and one line to use the same day. The quiz builds your path first; your first course is free, with AI feedback included.
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Questions people ask
Am I boring to talk to?
How do charismatic people make ordinary conversations interesting?
Is it rude to start a story in the middle?
Sources checked
- Hirschi, Q., Wilson, T. D., & Gilbert, D. T. (2022). Speak up! Mistaken beliefs about how much to talk in conversations. Personality and Social Psychology Bulletin. doi:10.1177/01461672221104927
- Dudukovic, N. M., Marsh, E. J., & Tversky, B. (2004). Telling a story or telling it straight: the effects of entertaining versus accurate retellings on memory. Applied Cognitive Psychology. doi:10.1002/acp.953
- Cooney, G., Gilbert, D. T., & Wilson, T. D. (2017). The novelty penalty: why do people like talking about new experiences but hearing about old ones? Psychological Science. doi:10.1177/0956797616685870
- Bavelas, J. B., Coates, L., & Johnson, T. (2000). Listeners as co-narrators. Journal of Personality and Social Psychology. doi:10.1037/0022-3514.79.6.941