How To Keep A Conversation Going

In this article, let’s explore how to keep a conversation going, why you run out of things to say, and questions to hold the conversation and keep it alive.

Not everyone can have the superpowers of confidence and spontaneity. The art of chatting for a long time requires some practice and some skill.

It doesn’t have to be a chore – you can start to love having conversations, even when networking. Let’s guide you through some steps to keep that conversation flowing.

How To Keep A Conversation Going

1. Use Your Right Brain

Your right brain is your “creative/artistic/dynamic brain.” Likely, if you’ve been working all day, maybe you have been using your left brain (logic/sequence/numbers…)?

If you wanna keep conversations going, realize that you’ll be using your right brain instead – and find a way to switch.

Having a friendly conversation is not a linear, logical activity – it’s dynamic and creative. The more dynamic your thoughts can be – the more you’ll be able to relate between subjects and come up with things to talk about on the fly.

That way, you’ll be able to talk and talk, without getting stuck in a subject and not knowing what to say next.

If you’re stuck in logic, you’ll quickly run out of things to say or your conversations will be “dry and serious” instead of “refreshing and fun.” Instead of using the logical/sequential part of your brain – you need to use the nonlinear/creative/ fun parts of your brain – your right brain.

Treat a conversation like you are about to tell a story or paint a picture.  You need to really believe you are about to make something wonderfully creative.

Remember to smile, have an open body language – roll your shoulders back – and move as if you’re feeling great. It’s a virtuous cycle – move your body as if you’re feeling great and you’ll feel great, then your body language will reflect it.

This will also help you access your creative right brain faster – because to begin with you will be pretending – until it becomes natural.

2. Know-How Much Time You Have Together

To keep a conversation going, you need to know how long can you can really talk to the other person.

Are you in a busy networking event, and only have a maximum of ten minutes to chat? Are you with friends for a long dinner conversation? You need to know because those are very different in terms of timing.

The longer the convo, the longer you can stay on any subject before going to the next. The shorter the conversation, the more succinct you need to be. But if you do have time, you can go into details of any topic as long as both you and others are interested in it.

Knowing how much time you have together is like an empty canvas – once you know the size of it, you can then draw on it whatever you want. It’s like an empty room you want to furnish – first you want to know how big it is!

3. Know What You’re Trying To Achieve With The Conversation

If you remind yourself why you’re talking to people, it’s much easier to hold a conversation:

• Are you getting to know a new friend?
• Catching up with an old friend?
• Trying to enjoy a nice evening with existing and new friends?
• Do you just want to destress and shoot the breeze?
• Do you want to laugh out loud and be silly?
• Want to discuss the important things in life?
• Do you have important information or news you want to share? Does the other person?

Those are simple reasons why you’re talking – and if you just ask yourself – “why am I here again?” – you’ll know.

And, if you know why you’re talking, then you know what to talk about – what mood to adopt – how funny or how serious you can be – how much to listen and how much to talk – etc.

Once you know why you’re talking, then you can hold a conversation as long as you want.

4. Lower that pressure.

You need to feel great in order to have brilliant conversations and keep them going. By the way – you deserve to feel great! It’s time to have a social conversation – you’ve been working hard – you deserve to have fun!

So, how do you do that? First, remember, you’re only responsible for 50% of the conversation if you’re with one person – 33% of it if talking to two people, and so on.

So, right off the bat, realize that at least 50% of the “task of conversation” is not on you – it’s on the other person.

Never assume that you have to “perform” for others. They’re not your customers – you’re not selling anything – you’re there to enjoy time together and maybe, potentially offer your friendship later on. You can offer a good company – but you’re never a performer.

5. Reach the “We Can Talk About Anything” point

If you want to have long and interesting conversations, you need to get to a feeling that you can discuss anything!

Once you get there, the conversation breaks come off and both you and others feel a sense of freedom to talk to each other as long you wish.

The way to reach this point is to talk about the simple things – for example – talk about how hard it was to park when you arrive. You could talk about what you’re drinking and why you prefer that drink – as if it was an important subject.

Then, talk about a very elaborate, intellectual subject if you want. You can then circle back to something simple. Then, maybe go on to talk about something deep and emotional, like a relationship.

Most importantly, say something that makes you seem very human – maybe a quirk you have – or something weird you do – or a recent mistake you made that was somewhat embarrassing.

Once you do that – you will feel free and confident. They feel that it’s safe to discuss whatever they want around you. You have unlocked all kinds of conversations and you may never run out of things to say again.

6. Be A Sponge For Content

You need to be a sponge for content. Whatever information you take on is now yours – whatever you watch, see, hear and read can be used in future conversations. This even includes other people’s stories.

You just need to mine those moments from your everyday experience and be prepared to share.

The details don’t have to be deep and meaningful all the time. You can chat about videos you’ve watched, listen to podcasts, television, books or music.

A conversation is just a way of channelling what you have experienced – and the more you are conscious that these are great topics to keep the chat going, the easier you will find keeping that conversation going.

7. Go From One Conversation Topic To Another Using Your Memory

You can keep forever if you realize that all conversation topics are linked, one way or the other. You can always say “that reminds of…” and share what it reminded you of. But you don’t really need a transition, you can just go to the next conversation topic because what’s being discussed reminded you of it.

Here is an example. I have this book…

That book reminds me of…

• The friend who gave it to me
• She gave it to me right before moving to Switzerland with her husband
• Switzerland reminds me of Austria, which reminds me of a movie I watched recently about a painting that was stolen by the Nazis, from an Austrian family. That painting is now hanging in a museum in New York.
• That reminds me of other museums I went to while in NYC.
• Which reminds me of all other memories from New York.
• Which reminds me of what I like and don’t like about it.

This can go on. I can then discuss the pros and cons of a few cities for living or for travelling. And a good question to ask would be “If you could live or travel anywhere in the world, where would you go?” That could easily become a 30-minute conversation about cities, geography, and travel.

You can do it with pretty much any item or any topic.

Let’s take… Math → studies → college → degrees → jobs → recently met a few lawyers → hard to keep a life balance when you work at a big law firm → same with finance → trading → are we in a financial bubble? → can you recession-proof your life? → how long do you think you’ll live? → if you knew you will live to be 100, how would you treat your body to keep it healthy?

I can go on and on, it’s all from memory. You need to realize that all topics are interrelated. And even if you have nothing to say about one topic, maybe you do have things to say about the next one.

8. Give The Conversation A Reason To Continue

Here is a conversation tip for you: “Hint at potential exchanges of value!”

That’s a fancy way to say that you can mention how you may have something the other person needs – and maybe they have something you need.

If you could potentially help each other in the future, then that’s a great reason to keep talking.

It can be something of tangible material value: maybe they need a new job and you are hiring people. Maybe summer is approaching and you have access to a beach house. Maybe their car keeps breaking down and you own a mechanic shop.

They may want to adopt a puppy and you volunteer at a pet adoption center!

If both of you can sense that you could help each other in some way, then that’s a great motivator to keep talking.

It can be intangible. Usually, an exchange of information and experience: maybe both of you are podcast fanatics and can discuss your favorite podcasts in the future. Maybe both of you are interested in the same scientific field.

Maybe both of you have ambitious goals and you can share success resources and motivate each other.

It can be a potential exchange of contracts: maybe as you talk, you realize that you socialize with similar types of people. Maybe both of you are networking in the same circles. Maybe they’re looking for a new house and you happen to know a trusted real estate agent.

Or maybe you know how to have fun (and talk about it) and they’re interested in having fun and meeting new people. It can be that simple.

As you talk, there will be hints of “potential exchanges of value.” And those potential ways you can help each other make both of you more interested in the conversation and more engaged in keeping it going.

Why You Run Out Of Things To Say & What To Do About It

First, understand that the fear of running out of things to say can make you tense and feel anxious. Most of the times – it’s not even your fault that the conversation got cut short! So let’s review a few reasons why conversations die off and what you should do when that happens.

The topic ran its course

Maybe you’ve spoken about a topic enough. Good! Before you jump on the next one, maybe both of you want a break. Maybe it’s time to fetch another drink, answer your Mom’s urgent-looking text, or go to the bathroom to freshen up. It’s entirely normal – there is nothing to panic about, keep smiling!

You don’t have much in common

This is another instance of “it is not your fault!” You’re not supposed to have things in common with everybody all the time.

When this happens, ask yourself this: “Do I have to continue talking?” maybe it’s your friend’s significant other, and you really want to get along, in that case, make an effort and keep talking about whatever comes to mind. It’s worth the effort.

If you don’t really have to make the extra effort – like in a networking event where there are other people you can meet anyway, then just move on. You’re there to meet like-minded people, you’re not there to force yourself to “hit it off” with each and every one of them.

You wanna talk to other people present

Sometimes, in networking events or while socializing with friends and friends of friends – both you and the person you’re talking to want to meet others too.

The conversation then arrives at a natural stop, as both of you are aware that there are others you should meet and greet. If that happens – you can excuse yourself to maybe get something from the other side of the room.

The other person will understand and will be glad that you’re a dynamic and flexible conversationalist. You’ll have a chance to “see them around” and continue the conversation later.

You’ve been talking for an hour, maybe it’s time to just “be” together

Sometimes, you’ve been keeping the conversation with friends for a while. Maybe you took the time to go into meaningful subjects and really got something from the interaction.

You’re feeling great – you’re connecting. There will be a time to take a break – and just enjoy each other’s company – absolutely no reason to panic, this is normal. Just “be” together – you don’t have to keep talking for hours on end.

You want to impress with impressive topics

Many people think that they are only allowed to say interesting, impressive, cool or hilarious things. Anything that falls short of that standard, they won’t say it. I used to be like that. I wanted to impress.

But I learned that this is counterproductive. If you “filter” what you say too much, you’ll have nothing to say – and you’ll pressure yourself too much. That means you won’t have a good time and your conversations will feel forced.

Instead, practice talking about mundane things… like how much you like the shape of the plate or the glass in front of you! This sends a message to your brain to relax and have fun instead of racing to say something impressive.

You think you’re not interesting enough

This is another mistake I used to make. You think that you have a regular boring life, therefore you can’t have great stories to tell. I have to ask you this: “So, what?!” Not every story or fact you say has to be from your life.

This is why I say “be a sponge for content” anything you hear, watch, read, or see – is yours. You can share anything interesting you know off – it doesn’t have to be your own adventure!

They’re too limited in what they can discuss

Sometimes, you’ll talk to someone and will try your hardest to get into different subjects (outside of work). But it won’t work – some people are too stubborn or limited to one or two subjects, and there is nothing you can do about it. It’s not your fault.

You can stay in that subject for a little longer, exchange contact information if you want to stay in touch. Then, move on. You are not obligated to have an interesting, diverse, and fun conversation with someone who isn’t willing to participate. You can just move on.

They don’t **really** wanna socialize

With some people, it’s a different story. It’s not that they can’t discuss a variety of subjects and be fun to talk to. Instead, they just have another agenda. They’re not there to socialize.

Maybe they’re only there to meet new clients (for whatever they’re selling) or maybe they’re only there to meet potential dates. Fine! To each their own. It’s not your fault. You can move on.

You keep misunderstanding each other

This is a tricky one. If you can’t listen and ask questions to understand what people really mean by what they say, then your replies will be off-topic for them. Anything can be open to interpretation – so make sure your interpretation is what they really mean.

This way, you avoid those misunderstandings that give that impression of “we’re not really connecting here, maybe we shouldn’t be talking – what’s the point?”

A weird subject came up and brought the conversation to a halt

Yes, sometimes, even if everything is going well, something will come from left field and throw the conversation into an awkward silence. Maybe a quirky friend of yours makes a sexual joke too soon around people you don’t know well. Just move on to the next subject, as if nothing happened; they’ll all be thankful that you did.

Here is another example – let’s say you’re talking to a woman you barely know:

• You: “Oh that’s an interesting necklace!”
• Her: “Thank you. It used to belong to my Grandma. She died two years ago, the poor woman!”
• You: “Oh, I’m sorry”
• Her: “It’s okay.”
• […silence…]
• You: “Where was she born?”
• Her: “A little town in New Mexico.”
• You: “Oh, really? My aunt lives in Albuquerque.”
• Her: “Really?”
• You: “Yes, she moved there many years ago (…)” on to the next conversation topic!

Even if a seeming “show-stopper” subjects come up, you don’t have to panic. There is always a way out. And you can appropriately move on and keep talking.

You’re just… hungry! (Or tired, or thirsty, or upset)

Sometimes, the reason there’s silence is because there is some pressing, physical issue or ache of some kind. You guys might be hungry, or thirsty, or just tired.

Other issues, like emotional issues, something annoying can happen that can throw off people and make them silent for a bit. It’s natural. Just be patient and resume the conversation little by little.

As you can see, there are many things that can happen that make you and other people go silent or run out of things to say. The main lesson is to not blame yourself every time it happens. If you can do something about it, that’s great – if you can’t, it’s okay.

You also want to be aware of why. Notice why people are not talking. When you know the reason, it’s much easier to resume the conversation and keep it going, the right way.

Questions to help keep the conversation going and invite the other person to keep talking

Instead of giving you word-for-word what to ask or what to say to keep the conversation going, I’d rather share with you the principles behind this concept. Some questions and comments just entice the other person into a deeper conversation, make it more interesting, and definitely keep it flowing.

Let’s take the following example…

Someone you’re getting to know says this: “I moved to this neighborhood last year. It’s a little bit farther from my job than before, but it’s okay.”

Here are some effective types of comments and questions to keep the conversation flowing.

1. Inspire an Opinion

“Oh, okay. So, what do you think about this neighborhood?”

2. Inspire a Story

“… Why? What made you move here?”

3. Ask for Information about them

“…Where did you live before?” or “Where do you work?”

4. Invite an Explanation

“Really…”; “Oh, interesting!” ; “Oh! Okay, I didn’t know that…” or “[ nodding and keeping eye contact – as if to say “I’m listening…” ]” or “ [raising eyebrows – which is usually a signal that the other person can keep talking ] “

In conversation science, this is called “backchanneling.” It’s what you utter or signal by your body language that tells the other person that you’re listening, paying attention, and want them to tell you more.

5. Inspire a friendly debate

“Oh, okay. I don’t know – living around your office is kind of a top priority, isn’t it?”

6. Give an opening for more ideas or stories

Here are some examples:

• “Yeah. Isn’t a great place to live?”
• “Isn’t it great that all the stores are walking distance?”
• “Doesn’t it looks like a great place to raise children?”
• “It feels like a pretty safe neighborhood – doesn’t it?”
• “Doesn’t it feel like it’s a new chapter of your life whenever you move to a new place?”

7. Inspire the connection momentum – “we’re in agreement”

“Yea, I think it’s worth it, even if it’s a bit farther from downtown.”

8. Go right into a story

“Yeah, I moved here two years ago, right after I launched my business/ got married/ divorced/ had kids (…)”

Note: When you quickly go into a story, you cement the conversation as friendly, open, and leading to a connection or new friendship.

9. Offer information about you – as if they asked, “how about you?”

“Oh yeah? I moved two years ago here, but it’s actually closer to where I work.”

10. Hint at ways you could connect or exchange value

“That’s cool! Well if you need landscaping, George here is the best guy in town!” or “Oh okay – are you part of the neighborhood association? (…) I think it’s valuable because (…) ” or “That’s great! By the way, there is a block party in a month, I don’t know if you are aware…”

In conclusion…

There is an infinite number of questions or comments you can ask to keep the conversation going. Practice with the different types: from a friendly debate to inspiring a connection, all the way to getting to know the other person even more.

Don’t focus too much on the content of the question or the comment – but rather, what kind of effect it has on the interaction and your potential friendship with the other person.

If you use these examples, you’ll never be stuck not knowing what to say next or having your interactions sound like an interview. You know that those are no fun.