How to Never Run Out of Things to Say

Running out of things to say is one of the most common problems people bring to me, and it usually arrives with a theory attached: "There is something wrong with me. Other people always know what to say." I want to put that theory to rest. When a conversation dries up, the cause is almost always technique, and technique can be practiced like anything else.

People that never seem to run out of things to say mostly work with what the other person tells them, rather than with a long list of topics. Once you see how that works, most of the pressure comes off.

Stop treating conversation like a quiz

When there is a lull, it is natural to search your memory for something interesting to bring up, as though conversation were a test of how many clever topics you can produce on demand. Under even a little pressure, your mind goes blank, and the harder you search, the worse it gets, because now you are nervous on top of everything else.

Good conversation mostly comes from responding to what the other person says. Instead of inventing fascinating subjects out of thin air, you only have to notice what the other person just gave you, and they give you something almost every time they speak.

Every answer contains at least three new threads

Listen to what an ordinary answer actually carries. You ask someone what they did over the weekend and they say, "I just got back from Portland, visiting my sister." That one sentence gives you at least three places to go. There is Portland (have you been, what is it like, why there). There is the sister (older or younger, are they close, where does she live). And there is the trip itself (the occasion, how long, first time up there). You did not have to invent any of that. All you have to do is pull one of the threads.

This is how it works. People share small pieces of information all the time, and each one is something you can ask about. When you stop trying to think up new topics and start following up on what people say, the conversation starts to keep itself going.

The follow-up usually beats the fresh question

When a lull is coming, the instinct is to change the subject entirely. Resist that instinct for a moment. Nine times out of ten there is something more interesting in what the other person just said, and asking more about it works far better than a brand-new question out of nowhere.

Say someone mentions they started rock climbing. You could pivot to "so where are you from," or you could ask the thing you are actually wondering: "Wait, are you scared of heights, or does that just not bother you?" The first keeps the conversation on the surface, and the second starts a real conversation without any cleverness at all, only curiosity about what they already told you.

Give them some threads to pull too

If you only ever ask questions, the conversation starts to feel like an interview, and the other person runs out of steam answering. The fix is to share a little information of your own, about a sentence's worth, with a few details they can ask about.

They ask how your week has been. "Pretty good, a little wrecked honestly, I started a new job on Monday and I am still figuring out where the coffee machine is." Now they have threads to pull: the new job, the fact that you are tired, and the small joke. When both people share details like this, neither one has to carry the conversation alone.

What about the silences?

You might be thinking, "That is all fine, but what do I do when it actually goes quiet?" First, not every silence is a failure. A short pause between two people that are enjoying themselves is normal, and treating it like an emergency is often what makes it awkward. Long gaps feel awkward mostly between strangers, while people that are comfortable with each other barely notice them. So a lull can simply mean the two of you are not fully at ease yet, and it does not mean you are bad at this.

If you do want to break the silence, you do not need anything brilliant. Comment on where you are: "This place is packed tonight. Have you been here before?" Your surroundings always give you something to talk about.

Why it stops feeling like work

At first you will have to do this on purpose. You will catch yourself hunting for topics, stop, and go find a thread instead. Do it enough times and it becomes automatic, and you will simply be talking with someone and asking about whatever you are curious about next.