How To Never Run Out Of Things To Say In Conversation

You’re talking, conversation is flowing nicely, and you feel like you’re really starting to form a connection with this person…

But what happens when after 10 minutes, that dreaded moment rears its head?

The awkward silence!

What should you do when you feel like a particular conversational topic has expired? And how do you never run out of things to say so you keep people engaged and interested?

Well, let’s take a step back to understand the awkward silence…

Who does the awkward silence seem to occur most with: strangers or friends? Undoubtedly, strangers. But why? You’d think there would be so much more interesting ground to cover with strangers. With friends, you know how they feel about the most important topics. You’re left with just random stuff that pops into your head. Yet you still can find yourselves talking for hours in a stream of unrelated randomness. Without any sort of agenda, conversation just flows.

This is exactly the point. When you feel like you’ve run out of things to say with strangers, you haven’t actually run out of things to say. You’ve simply run out of things that have passed your internal filter of “good enough to say to a stranger!”

This is why you can talk for hours nothing with people you know well. Why you can turn a conversation about “nothing” into something you both really cherish. It’s not just because you have common interests. It is because neither of you has a very high threshold for what is “good enough” to say. If something pops into your head, you blurt it out.

This is also why it is much easier to speak to people when you’ve had a few drinks. It’s not that you’ve suddenly become more clever or interesting (sorry to burst your bubble!) It’s that you’ve lowered your inhibitions. You say what comes to your mind without thinking if it is “good enough” to vocalize.

The key here is that you are not anticipating too far ahead. You need to trust yourself to adapt on the fly.  You need to remove the filter.

Here is an example of “removing the filter” to apply in your own life

I was working with a client who was also working with a personal trainer. She recounted a story from the day she met him.

“He asked me, ‘So what’s your story?’ and I was just so taken aback. It’s such a big question. I didn’t even know where to start. So I just mumbled something awkwardly and then got quiet.”

“Well what was going through your head?”


“No that’s not true. Something was going through your head. You just didn’t think it was good enough to say. So what was your thought process?”

“I guess, ‘Oh wow this is awkward. I can’t even answer a simple question about my life! Now he probably thinks I am a weirdo…'”

“Great! Use that.”

“What do you mean?”

“I mean imagine what would have happened if you’d dropped the filter and said that to him. What would it have gone like?”

“Well I suppose I would have said, ‘Oh wow this is awkward. I can’t even answer a simple question about my life! Now you probably think I am a weirdo…”

“And what would he have done?”

“Laughed probably. And clarified his question.”

“Exactly! The point is that what you are thinking is always good enough – at least better than saying nothing because you only want to sound super clever all the time.”

The difficulty for everyone — my client, you, the best conversationalist on the planet — is not in coming up with something to say. It is in getting in touch with your thoughts and trusting yourself enough to simply state them. Will they always paint you as a genius? Certainly not! But by speaking, you’ve given both you and the person with whom you’re speaking a starting point. Now you have some Velcro hooks which either of you can latch onto.

So for example, the other day I was out speaking with a girl at a club. I didn’t have anything to say, but I noticed that she had a very genuine smile whenever she spoke to people. So I told her what was going through my head:

“You know you have such a genuine smile? It makes you look like a first grade teacher.  I feel like I just want you to read me a picture book.”

When you remove the filter, what you say will rarely be brilliant. But it will provide you with enough “hooks” to start to restart conversation.

Note: if you’re absolutely stumped, I find a great way to start or restart a halting conversation is to simply say, “So what’s your story?”

Play “Reminds me of…” to re-spark dying conversation

So once you’ve cleared the filter, the goal is to drive conversation back to something that is fun or fascinating to both of you.

You don’t want to be trapped with just sticking to the literal words at hand. So if we’re talking about the weather today, I shouldn’t be limited to just talking about the weather this week. I want to be able to make conversational leaps.

One of the best tools to do this is, “Reminds me of.”

“Reminds me of” consists of thinking not just linearly (i.e. weather today > weather this week) but in larger leaps (i.e. weather today > gorgeous weather > the vacation I took last year to Costa Rica when it was sunny and then poured on us as we hiked up a mountain.)

“Reminds me of” can also be used to re-spark conversation with someone to whom you’ve already spoken. For instance, last night I was out at a bar with an extended group of friends. I was standing watching a drummer play a solo. We’d already exchanged pleasantries so I didn’t have any questions to ask many of the people. Still, to re-spark conversation, all I had to say was:

“This guy is amazing. He reminds me of Travis Barker from 182.”


“This club is so cool. It reminds me of a 1920’s speakeasy mixed with a rave.”

Use “reminds me of” in conjunction with the fun and values modes of conversation to rekindle any conversation and move it in a direction that will keep people captivated. It’s also a fantastic tool for connecting with someone with whom you may not have much in common because it allows you to trade stories based on whatever is happening around you.


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11 thoughts on “How To Never Run Out Of Things To Say In Conversation

  1. Such great content! What I liked the most was when you mentioned not to give in to your filter and don’t concern yourself with being a genius. That’s probably why most people are too scared to speak freely to others. They’re too worried about not appearing as smart as they want to be.

    1. Yeah and it’s especially unfortunate because genius thoughts aren’t formed in the quietness of our mind. If you watch the best comedians or speakers, you can see that their process is iterative. They put something out there, then build on it in ways they couldn’t have anticipated

  2. Good article. I want to note that while for some people breaking the filter helps to keep convos going, There are others like myself who need that filter to keep convos going. I think it is a two way road. Without a filter i might freely talk about the existence of alien life, which is sure to drive people away and kill a conversation.

    1. Whats wrong with talking about the existence of alien life? Its something you genuinely like. If people don’t want to talk to you because of that, they are the problem, not you

  3. Excellent article! One thing I use too is telling people I don’t believe in awkward silences because I don’t find them awkward. That’s actually true most of the time. It also makes people more comfortable to talk about things because they don’t feel like they have to avoid awkward silences, but because they know I wouldn’t mind if one were to come

    1. also if you tell some one that its ok to feel comfortable that will help be more open to not create awkward silence that happend with me and my girlfriend i felt uncomfortable because i didn’t want to say anything wrong so i was just silent until she said its ok to talk i wont judge that then gave me the confirmation that its ok to talk about whatever was on my mind

  4. Wow. Such a great content. I like how you understand people in a way that they don’t understand themselves.

  5. I am an introvert. I try to converse people but I often lack in the communication of expressions and run out of words. sometimes I really don’t like talking to people and this has gotten me into a lot of trouble lately.
    I need help and suggestions for maintaining a good conversation.
    your article helped me a lot. thanks.

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