How to Keep a Conversation Going

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Ah the awkward silence – the death of any social situation. Once a conversation reaches that point any other topics can feel a little strained and difficult but sometimes it just seems hard to avoid getting there. Well there’s a knack to avoiding an awkward silence without talking about inane things at the same time. Learning to keep a conversation going is an important skill to learn and can really help you overcome shyness in the long run. Now the trick to this is not to try and memorize some topics to keep using in conversation but to learn how to learn how to keep a conversation going organically.

In our training course for overcoming shyness we cover a few special tricks like conversation threading and how to abuse the ‘cave man brain’ (which is the reason we feel shy in the first place) into carrying an easy conversation for us. Really though we just use these to get the practice in keeping small conversations going so it eventually becomes automatic.

Personally I can still remember what it was like to NOT be able to keep a conversation going. To start with it took work and I had to keep the techniques and practices in mind for every sentence I tried to get out of my mouth but now I carry a casual conversation and it just happens. That’s the end goal but we’re going to take baby steps to get there.

So I’m not going to show you how to ‘trick’ people into thinking that you’re having a conversation when you’re really running through a script in your head. I’m going to show you how to actually have a conversation with anyone and keep it going as long as the both of you want. And how to make it flow easily without becoming awkward. It’s one of the best things you can learn to improve your social skills and social life in general.

Now I always say the same thing here but I think it’s important to remember. If you’re struggling with shyness then it’s important to learn how to keep a conversation going – but it’s also important not to force yourself into situations which you know will go badly. You need to take things slowly and retrain the lower levels of your brain. Throwing yourself into the deep end can certainly make things worse, so take things one step at a time OK? That said learning to keep a conversation going smoothly can really help your confidence when it comes to social situations where you’d normally worry about ending up in an awkward silence.

To start with you might need to remind yourself of these techniques but as you continue things will get easier. Eventually you’ll be able to carry a conversation easily without even thinking about it.

Social skills are just that – a skill and they need to be learned just like any other skill.

If you’re sick of reading about making a change and want to actually learn how to make one CLICK HERE.


Keeping a Conversation Going Organically

So to start with you might need to change how you think about conversations. It doesn’t just come out of nowhere and even if you’re really ‘clicking’ with someone you both need to take responsibility to keep conversation going. If one person is trying to keep the conversation going alone it’s going to seem very forced. Some people just naturally keep conversations going without thinking about it – and with a little practice you can do this too. But to start with just try and mentally remind yourself to work at a conversation.

Be Interested

how to keep a conversation goingIf you’re frequently talking to people you’re comfortable talking to or you’re panicking when talking to strangers then you might be in the habit of not really paying attention to what they’re saying and keeping your attention inside your own head. Forget about everything else. Stop worrying people are watching everything you say or do. Get out of your head and pay real, genuine attention to what they’re saying.

When someone in a conversation isn’t actually listening and is just waiting for their turn to talk? It’s not going to last and it’s obvious to the other person when you’re doing it. Listen to what they’re saying and respond to it. This is the first thing you really need to do to keep conversations going.

Questions to Keep a Conversation Going

If you listen to a normal conversation going on around you they flow naturally with exchange of information and questions and this is what you need to learn to do.

I looked at this before in the social awkwardness guide. The best way to keep a conversation going is to keep asking questions. Rather than trying to bring up new topics constantly just keep asking questions. If someone’s trying to keep a conversation going with topic points it’s not going to flow normally. If you ask open ended questions and then follow that with follow up questions it will flow a lot better. When you’re asked a question you can follow your answer with a question as well. Asking open ended questions is an easy way to keep a conversation going and is probably the easiest way to avoid an awkward silence.

Use a little common sense here and don’t be too intrusive with strangers, unless it’s clear they want to talk about it of course. Ask questions relevant to the topic and you can follow up with your own experiences – if they’re relevant to the topic. Avoid steering the conversation to you the whole time but don’t feel that you need to constantly ask them questions if you have something to add which is relevant. Try to find an even balance and that will lead to a positive conversation.

Topics to Keep a Conversation Going

If you’re struggling for a topic to start a conversation or move one on from small talk then I’ve a few suggestions for you. I don’t really advise ‘conversation points’ because you’re trying to learn to keep a conversation going naturally. Instead focus on things which are going on around you or common interests you both might have. If you’re at a class or activity for example then you have an obvious talking point and it’s easy to get into the topic with a question about it.

You can use topics from the media but this can be a stickier area. It’s better to stick to the bigger or better known events, and avoid the controversial subjects unless you know how the feel about it before hand. And certainly avoid the ‘small talk’ subjects such as the weather. It’s one way to start a conversation if you don’t have anything else but it’s a great way to kill a conversation because it’s going to feel a little forced after that.

You can never always know the right topics to talk about, especially if you don’t really know the person you’re talking to. And you’re never always going to say the right thing – but one piece of advice I can certainly suggest for this is ‘just say it’.

Just Say It

Too many times in conversations I used to find myself going silent because I didn’t want to say what was on my mind. I was worried how they’d judge me for saying it even if the topic wasn’t very controversial I’d worry about how it would make me look or that the person wouldn’t like the subject. This led to the death of many conversations.

So now I work with my new rule – I just say it. I obviously filter myself from the controversial topics but otherwise I’m just going to say what’s on my mind. If it doesn’t interest them we’ll move on to another topic and if they don’t agree we might discuss it which leads to more of a conversation but few people are actually going to care that much about something I say. And personally I don’t think people change. I’d rather share my opinions and talk to people who share my interests (even if we don’t always agree on everything) than not talk to anyone and worry about what I’m saying constantly.

So get out of your head and just say it. Some people have a problem having ‘no filter’ and saying whatever comes to their mind which doesn’t work out so well. But because you’re reading a guide on conversation skills it’s safe to say you have too much of a filter. So let yourself go a bit and blurt it out, you’ll still have the sense to avoid the subjects the people with ‘no filter’ would probably bring up.

Eye Contact

conversation skillsI’ve spoken about this before but it’s an important part of any social interaction. Keeping eye contact might come easily to some people but if you don’t find it natural then you need to practice it. If you feel like you’re constantly staring at someone then do it in bursts. If two people are talking about something which they’re both interested then it’s normal for them to make eye contact for roughly 30-60% of the conversation. This can vary if you’re talking during an activity which requires attention or if the other person has a problem with shyness and eye contact of course.

I’ve already looked at how to properly keep eye contact but it’s basically just something you need to work on. It’s an important part of conversation and the more you do it the more you’ll get used to it. If you’re having a problem with meeting people directly in the eye then focus on the top of their nose between their eyes. It might feel more comfortable for you and they won’t be able to tell the difference.

Conversation Threading

A good way to think of keeping a conversation going is a technique called conversation threading. Each part of a sentence can be dissected into parts and you can follow that part of the thread to keep a conversation going.

For example:

Beth: “I’m just back from France I’m completely jet lagged but I’m supposed to be at work in the morning.”

Here there are three conversation threads you can follow. The fact that’s she’s just back from France, the fact she’s jet lagged and her job. Generally (and I know this sounds cynical but it’s true) people talk about topics with others because they want to talk about it themselves. So picking any of these threads in a conversation (even if they’re posed as a question) can be a great way to continue a conversation.

So there for example you could ask about her trip to France, tell an anecdote about your own jet lag or ask about her work. Then you can follow a new thread from her response.

“I was in Paris for a week visiting family. It wasn’t the first time I’ve been but it’s always my favorite place to go.”

Here you can pick out some more threads. You could ask when she’s been there before, what she likes so much about it or where else she goes. You could also ask about the family she was visiting but maybe gauge the tone here. You don’t want to drag down a conversation with a stranger about a family member on their death bed.

Always keep in mind you’re not looking to make this a game of 20 questions. If they’re engaging in the conversation as well they’ll ask questions and you should answer them without just rushing to another question. It’s a conversation, not an interview.

If you do find yourself at the end of the thread and they haven’t offered anything new (like getting a one word answer) then do one of either two things. Either this is the point to let a conversation end (see below) or you can loop back to an earlier thread.

“So you said you said you had work in the morning. What will your boss be like if you turn up late?”

The idea of threading a conversation like is probably the easiest way to keep a conversation going. It can take a little practice to get right but it’s easy to remember and leads to a more organic conversation.

Practice, Practice, Practice

It becomes a bit of a vicious circle, but the more you have people to talk to the easier you’ll learn. That’s why if you can actually say I have no friends you’ll need to start slow and ease yourself into this. Learning how to keep a conversation going is possible from home so practice a bit and slowly ease yourself into tougher situations. Family is also a good fall back and once you’re feeling more comfortable with your conversation skills it’s easier to move from there.

Regardless who you’re talking to you should be working on the conversation. Even if it’s an old friend or family member – if you keep working on your conversation skills with people you’d normally be comfortable in silence with it’s going to help your social and conversation skills even further. Talk to people around you, talk to people online, talk to people standing next to you in line. Just talk to anyone you can. Even the loudest extroverts out there have learned how to keep a conversation going at one point and every time they talk to someone they’re just reinforcing these skills. It’s the same for everyone, the more you talk to people the more natural it will become and eventually you’ll forget even reading this guide.

Start small. Ask them a question about their day, ask them about the online chat service, ask them about whatever you’re queuing up for. Just get a conversation started and take it from there. Even if it’s a short conversation it’ll keep the techniques fresh in your mind and boost your confidence. Become a complete chatterbox and talk to anyone and everyone. You’d be amazed at how easily it all becomes the more you talk to people and eventually it’ll just be second nature to keep a conversation going easily.

Digital Conversations

It’s entirely possible to practice your conversation skills online or through phone texting. Just remember that this doesn’t really compare to a face to face conversation and you’ll have to push for that at some point. But it doesn’t hurt to talk to people online when it’s just not possible to meet people face to face.

Ideally you want to use voice or video chat for this. It’ll get you as close to a spontaneous conversation as you can really get online while using a chat or IM service, email, forum or phone texting can give you too much of a gap to think about what to say next. Learning how to keep a conversation going like this is exactly the same, except you also need to avoid the far too common conversation killer ‘lol’. Don’t follow everything they say with something like this, follow it with questions and actual meaningful conversation the same as you would in a face to face conversation.

When to End a Conversation

The more you practice these techniques, the easier you’re going to find it to keep a conversation going without even thinking about it. Your problem then (if you can really even call it a problem) is not going to be learning how to keep a conversation going – but how to end a conversation. I’ll look at this in more detail in another article but every conversation must end at some point.

Look for the signs of the other person wanting to end it. Looking for the time or slowly taking a step or two away are the obvious ones. Some people will be too polite to end a conversation but don’t push it when it’s obvious they want to leave.

If a conversation is becoming one sided and the other person is obviously not making an effort with you then it might not be worth keeping a conversation going. They might just be distracted or perhaps shy but if your attempts at keeping a conversation going are being met with one line answers and a lack of enthusiasm then it’s time to move on.

How to End a Conversation

Strive to end every conversation positively. Politely let them go or parson yourself and you’ll leave the opportunity for another conversation in the future – keep them and they might want to avoid a repetition.

If a conversation is going well then try to get into the habit of ending it with a follow up. Asking to exchange contact details or continue the conversation and meet up another day might seem pretty daunting at first. But as your confidence grows it’s something which can certainly improve your social life pretty quickly.

Next Steps

The key thing to remember in learning how to keep a conversation going is practice. Nothing will help you improve your conversation skills other than talking to people. I’ve linked a few other guides above which can help round out your knowledge as well but just keep practicing.

Now not everyone who has a problem keeping a conversation going will have a problem with shyness. But statistically around 40% of people feel shy in one situation or another and it can certainly put a dampener on your conversation skills, let alone your social life.

Social skills are just that – a skill. You can’t walk right on to a Tennis court and play against a seasoned athlete can you? No. And you would expect to be able to because it takes training. Well social skills are exactly the same, we’re just expected to have learned them at some point and not everyone does.

If you’re looking to add a little extra kick to your social training and see the quickest possible improvement then take a look at our online training course.

keeping a conversation going

22 Responses to “How to Keep a Conversation Going”

  • Mandi

    I have a hard time keeping a good conversation going past the first two sentences. How long does it take to improve?

    • Chris

      It will take longer for different people it can really all depend. But it’s not a race, do your thing and keep working at it you can see some results *very* quickly but don’t push yourself too hard.

  • Mandy

    Thank you so much I think this is helping me already just to understand things better.

    • Chris

      It’s the same when dealing with shyness. A little understanding of the problem in the first place can make all the difference.

  • Denise

    I’m not sure if I’m actually shy or just socially inept at having a conversation. I cannot tell the difference but if I fix the one I guess I will know about the other.

  • Jordan

    Just wanted to come back and leave a quick message. I was actually here a few weeks ago and told myself I would come back and share the good news so I’ll force myself to do something new.

    My conversations used to be the same. Someone else would start them (because I was too shy) and I’d usually run out of things to say and the conversation would die out and they’d start talking to someone else instead. But now things are better for me I’ve followed a lot of advice on keeping conversations going and so far it’s much better. I’ve actually got people I talk to on a regular basis and I don’t mind talking to new people quite as much.

    Who knows maybe if I keep this up I’ll even be able to start a conversation of my own!

    • Chris

      That’s great to hear Jordan. Keep it up and you’ll keep improving. Keep getting social exposure and you’ll have no trouble starting your own conversation.
      If it helps take a look at the quick guide on talking to strangers:
      Congrats and best of luck for the future.

  • Shany

    Keeping a conversation going is one thing but what about getting one started? I’d love to be able to let a conversation die out if I could at least start one…

    • Chris

      Well you’re in the right place. 🙂 Have a read through some of our articles and it can help you narrow down where your problem areas are.

  • Chase

    This is some really good stuff man thanks. Going to be trying it out later. I usually dread starting talking to people because after the first line or two it just seems kind of awkward and I have to get away.

    Hopefully I can keep this in mind and learn to keep it lasting a bit longer at a time. I’ll let you know how it goes!

    • Chris

      Good luck, looking forward to hearing all about it.

  • Sig

    One thing I found which really helps (if you don’t mind me adding my advice here) is that keep in mind everyone is different. You’re not going to be able to talk to everyone because sometimes people are just different. Don’t worry about trying to please everyone but talk to the people who you genuinely get on with. Then it’s worth actually keeping the conversation going in the first place.

  • Amcii

    I am shy, unconfident, have very low self-esteem, isolate in a hermit-like way and have no friends at all. Have a boyfriend who greatly misunderstands me due to my poor way of communicating with him. I am miserable and have nothing fulfilling in my life. My anxiety is incredibly painful even when alone and I have many fears that keep me alone and feeling bad and prevent me from action in moving forward in any way in my life.

  • Pulchritude

    I am 19 year old a girl and a kid i stay away from everyone, to be honest ur just like me and I can’t talk i hate my voice because I sound like a gosh darn mouse! and people think I’m shy but I honestly don’t know if I am so I just can’t be myself in public only when I’m writing to someone or just typing. Heh, this is how I reallllly act…

    • Chris

      Heya Pulchritude,

      It sounds like you might be at least a little shy. But don’t panic!

      Everyone experiences shyness a little differently and you’re in the right place. Take a look at some of our shyness guides and just start applying them in your daily life – see how it goes!

  • Joel

    Hello, am a very shy guy but luckily for me, i managed to get a girlfriend after so much beating around the bush. But am having problem keeping a conversation going or even starting up one to the extent that i don’t call her cause I’ve got nothing to say…. Whenever she calls and tries to have a chat, the shyness in me kills it. Am getting scared she might have the feeling am not interested in her anymore… please help me.

  • Dylan

    Hey chris, thx for all these tips and stuff. I haven’t always been shy and nervous, I only ended getting shy and nervous when I went into yr 7. I’m now in yr 11 and I’ve got a group of friends but I feel that I’m nervous around other people outside of my group (people that I’m not friends with). You pretty much covered that though and I just wanted to thank you!!! Hopefully I can improve on my skills and be able to rewire whatever is going on in my head and have a different approach in the way that I communicate with other people

  • Lynn

    I’ve been shy the majority of my life. It’s gotten better as I’ve gotten older. I’ve started new jobs, been to college twice no problem. When having conversations I usually feed off the other person, facial expressions body language. I actually do ask a ton of questions, and I find some people seem more nervous than I do. But I had this one boyfriend when I was young for a long time. He was the Center of attention, life of the party all the time. When we would go to weddings or gatherings, he would instantly leave my side. Leaving me in a room full of strangers feeling awkward and alone and unsure how to just approach someone. I would have to introduce myself to his friends and family. Already being shy it was horrifying. Now meeting family and friends of a significant other is terrifying. Now in a new relationship I was asked to go on a camping trip with a bunch of other friends. Instant anxiety, I was terrified. This is the area where I really struggle with shyness. I was upfront and honest about my shyness which he was very understanding considering he is quite shy as well (lol interesting when we were first getting to know eachother) But I asked him if I could meet his friends individually first. But your site, very helpful thank you

    • Chris

      Hi Lynn.

      Being suddenly put into a position like that can certainly set off a few shyness triggers. Being honest with the other person is definitely the way to go. Even if they don’t understand shyness first hand just explaining how you feel is a good start. Conversation threading or feeding off the other person is the right way to do it. Don’t be tempted to try and script a conversation ahead of time. Most people love to talk about themselves or their hobbies so just get them to do the heavy lifting in a conversation and add what you can. The rest will come.

  • Niku Parker

    Hi i have to thank to this guy he saved me i wass already getting better from being shy but i still had some wen i watched and bought this programme i got the things i needed to fight it i thank you soo much (sorry for mi eng im from portugal)

  • Annie

    Thank you! Specifically on how to Just Say It

  • Shaquanna

    I need help keeping a conversation. I am really cool and have a lot of awesome experiences to share, but I always shut down. Another bad habit is I’ll change the topic every five seconds after that awkward silence.
    I’m not shy because I can present a speech to millions of people. I just have this huge fear of boring people. So I dig for things they’d be interested in and try discussing it.

    Long story short I could be perfect for them and this flaw will usually turn them away. Help!

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