How to Keep a Conversation Going Without Running Out of Things to Say

Conversations keep going when each reply gives the other person something to pick up. That usually means one of two moves: a follow-up question about what they just said, or a bit of your own that connects to it and hands the turn back. Do those two things in rough alternation and you will rarely run out of things to say.

Running out of things to say is almost never a shortage of topics. It is answering closed, asking a brand new question instead of going one step deeper on the current one, and treating silence as an emergency. All three are fixable with practice, and none of them requires being naturally chatty.

Why conversations stall

• Closed answers. “Good, thanks.” “Yeah, it was fine.” Nothing to grab hold of.
• Interview mode. One person asks, the other answers, repeat. It feels like a form being filled in.
• Topic-hopping. Job, then home town, then holidays, then pets, each abandoned after one exchange. You burn through topics fast and then genuinely are out.
• Waiting your turn. Planning your next line instead of listening to theirs, so the next line doesn't fit.

How to keep a conversation going without running out of things to say

Follow up before you change the subject

Before you reach for a new topic, ask one more question about the current one. Research led by Karen Huang at Harvard in 2017 found that people who asked more follow-up questions were better liked by the people they spoke to, and that hardly anyone predicted it would help. A follow-up tells the other person you heard them, which is most of what people want from a conversation.

• “How did you end up doing that?”
• “What was the hardest part?”
• “Wait, go back. You lived on a boat?”
• “Would you do it again?”
• “What did your family make of that?”

Share back, then hand it back

A conversation is closer to a rally than an interview. After their answer, offer something of yours that connects, then return the ball.

“I've just started running again.” “Oh, I keep meaning to. I did a couch-to-5k once and quit at week six. How are you finding it, is it actually getting easier?”

One related story, one question. Not a twenty-minute anecdote, and not a story that tops theirs. The point of sharing back is to show you have a stake in the topic too, which makes it feel mutual.

Give answers with handles

When someone asks you something, give a little more than the minimum. One extra detail is a handle they can pick up.

“Where are you from?” “Leeds.” versus “Where are you from?” “Leeds, though I've spent ten years in London trying to lose the accent and failing.”

The second answer gives them three things to ask about. You are not oversharing, you are being generous with material.

Keep a loose list of threads

Every conversation throws up threads that get dropped: a sister mentioned in passing, a move, a trip coming up. Notice them. When things go quiet, go back to one: “You mentioned your sister lives in Glasgow. Do you get up there much?” Calling back to something from earlier is one of the most reliable ways to restart a stalled conversation, and it shows you were paying attention the whole time.

Let a silence be a silence

A pause of a few seconds feels enormous from the inside and is barely noticed from the outside. You don't have to fill it instantly. Often the other person will, and what they say after a pause is frequently more interesting than what they said before it.

How to keep a conversation going over text

Text has its own problems. There are no faces, no tone, and every message is a chance for the other person to quietly stop. The same principles apply, adjusted:

• Reply to the content, not just the fact of the message. “Haha nice” is where text conversations go to die.
• One question, not three. A paragraph with three questions gets one of them answered, and it's never the one you cared about.
• Add a bit of yourself. “That sounds brilliant. I've wanted to try climbing for ages but I'm scared of the falling bit. Was it hard the first time?”
• Send the thing. A photo of what you're cooking, the song that's stuck in your head, the sign you walked past. Low-effort, easy to reply to.
• Don't panic about pace. Texting isn't a live performance. Replying in an hour, or tomorrow, is normal.

Text threads also fade naturally, and that is fine. A conversation that rests for a few days is not a failure. Reopen it with something specific rather than an apology:

• “Saw this and immediately thought of your landlord saga.”
• “How did the interview go in the end?”
• “Update on the sourdough: it's alive and I'm scared of it.”

For friendships that mostly live over text, this kind of small, regular contact is a lot of what keeps them alive. How to maintain friendships as an adult goes into that properly.

Going one layer deeper

Sometimes a conversation is going fine but feels stuck at the surface. You can move it down a layer by asking about experience rather than facts. Not “what do you do?” but “what's the part of your job nobody understands?” Not “where did you go?” but “what surprised you about it?”

People tend to assume others want to keep things light. In 2022, Michael Kardas, Amit Kumar and Nicholas Epley ran a series of experiments where strangers were given either shallow or deep questions to discuss, and found the deeper conversations went better than people expected: warmer, less awkward, more connecting. If you want questions to try, there is a long list of deep questions to ask friends, sorted by how far in they go.

And when you ask something real, be willing to answer it yourself. That is most of how opening up to people works.

How to end a conversation well

Keeping a conversation going is only half of it. The other half is stopping it at a good point, which most of us are bad at.

A 2021 study by Adam Mastroianni and colleagues asked people how long they had wanted their conversations to last. Only about 2 per cent of conversations ended when both people wanted them to, and many went on longer than either person would have chosen. Neither side says anything, because both assume the other is enjoying it.

So end on a high rather than letting it run down. Name something you enjoyed, give a simple reason, and if you want to see them again, say so:

• “I'm going to head off, but this was really good. Let me know how the move goes.”
• “I need to go and rescue my friend from that corner, but I'd love to carry this on another time.”
• “I've kept you ages. Thanks for telling me all that, I genuinely want to know what happens next.”

A conversation that ends while it is still good leaves both people wanting another one. That is a much better position than one that ends because it ran out of air.

Where Spillr fits

If you like the slower kind of conversation, Spillr's Scrolls are built around it: one letter a day to a stranger, who can reply once within seven days, and if you both say yes it opens into a chat. It is a good place to practise the handles-and-follow-ups rhythm in writing, with someone who has no idea who you are and no reason to perform.