Avoid Awkward Silence - 5 Tips to Keep a Conversation Going

Handsome man holding a mask

Do you ever feel like a conversation is just dragging on aimlessly? No one seems to be enjoying the convo and when it's your turn to utter something mildly interesting or entertaining, the words that you blurt out seem to only feed the awkward silence that engulfs the room. 

And while you're hopelessly trying to string together the sentences to convey your message, your partner is looking at your face in disbelief, trying to figure out which planet you hail from. 

Do you often feel alone even though you're surrounded by a bunch of people? Do you feel uncomfortable trying to start a conversation with a stranger? Are you obsessed with what other people might be thinking about you? Or what they might think once they hear what you have to say? 

Don't worry, you're not alone.

High School Years Muffled By a Thick Veil of Awkward Silence

Shy man peeking

For example, I have spent the majority of my high school years withdrawn into silent solitude. And even though I like to tell myself that it was ultimately my decision to choose the fate of a social outcast, if I'm brutally honest with myself, I have to admit that part of it had to do with my inability to start and maintain a conversation. 

I was simply obsessed with the opinion of other people.

Whether it was the opinion of a classmate, a teacher, or a colleague, I've always allowed their opinions to powerfully impact my self-esteem.

And of course I had several friends who would try to help by saying things like:

"Who cares what they think? Just ignore the opinions of other people."

If it only it had been that simple. For a very long time, I was unable to not care about what pepople thought about me. A simple conversation with the lunch lady felt like a popularity contest.

I wanted to impress everyone around me. 

Because deep down I believed that as soon as I opened my mouth, people would immediately find out that I'm boring, weird and that I'm wasting their time. As I was formulating my sentences, the cold realization washed over me that what I was saying was boring fluff.

And the more I was trying to be assertive and seem confident in myself, the more I felt like people could tell... they could tell that I was trying so hard to hide something to blatantly obvious.

So with time, I got used to the fact that whenever I would start talking to someone, their immediate reaction would be to ask me to repeat what I had just said. They were bracing themselves for the second iteration of my mumbling, their face submerged in concentration. 

"Speak louder! Stop mumbling under your breath!"

Needless to say, during my high school years, I wasn't one of the "popular kids." In fact, I wasn't very social at all. For several years afterwards, a trivial thing like a conversation with the grocery clerk would be enough to fill me with crippling social anxiety.

The Price of Shyness

Woman gesturing to stop

Being shy is not a walk in the park. 

My lack of social skills made it very challenging for me to make friends. Friendships often start with a spontaneous but pleasant conversation. 

But the chances of a spontaneous chat ending well for someone struggling with social anxiety are very slim. 

From this perspective, having internet, being able to chat online with someone and send them emails was a godsend. It made getting to know people and making friends so much easier. Arming myself with the inherent anonymity of the internet, I was finally able to practice my feeble social skills virtually without any consequences. 

But even with the widespread popularity of the internet in later years, little did it change the core of the issue: a conversation in person would still freeze my brain and make me embarrass myself. My humor, my friendly attitude and my welcoming demeanor would be dispersed and instead a noisy, confusing cloud of anxiety would rear its ugly head, block my memory and steal my ability to speak. 

And what about dating?

Well, let's just say that if the thought of a friendly exchange of words with a stranger makes you nervous, then talking to an attractive member of the opposite sex is going to give you a mental breakdown.

The Benefit of Charisma

Man looking at statue

So it pays if you have a silver tongue and you know how to keep a conversation going.

I learned that the hard way.

At one point in my life during my college years, I was able to disarm a street thug who tried to rob me using nothing but words.

Don't get me wrong, it was by no means an easy feat. I was traveling by streetcar in downtown when a young man walked up to me as I was leaning against the window and casually told me that I was to hand him over my wallet and my cell phone or else he would beat me up/stab me/shock me with a teaser. I can't remember the exact order of these threats but he sounded pretty convincing to me.

I can't remember exactly how it all happened. All I can recall is that I offhandedly mentioned to him that I study Japanese. This caught his interested and so he asked me to say something in Japanese. I was happy to oblige lest he follows through with his threats and candidly threw some choicy Japanese curse words at him. He seemed to be enjoying himself. 

Before I knew it, we were enjoying ourselves lost in conversation. For all the passengers on the street car we must have seemed like two old buddies. 

And then it happened. 

He leaned closer to me, shook my hands and told me that I got a pass that day because I was cool. And with that, he got off the street car and disappeared into the bustling crowd of people walking along the streets of Budapest.

That was the first time that I managed to disarm a criminal with nothing but words.

How to Keep a Conversation Going Indefinitely - In a Way That Your Partner Enjoys It

And now I want to share with you how you, too, can keep a conversation going on forver without making it seem forced or artificial. 

#1 Speech is Silver, Silence is Golden

Woman and monkey

Good speakers are easy to find. But good listeners are truly rare. 

In many cases in order to keep a conversation going, all have to do is let the other person speak their mind for as long as they want and silently stay in the background. 

The good news is, it's very easy to do if you're a little bit shy

You see, the majority of people love to be the center of attention. They love the spotlight and they'll take every chance they get to hog it. But that's not very enjoyable for their conversation partner, is it? 

On the other hand, if you gently step aside and let your conversation partner steal the spotlight for themselves, they'll love you for it. If instead of trying to interrupt them every other minute, you give them your undivided attention, you'll be doing something refreshing and they'll really enjoy their time with you. 

Never underestimate the power of silence.

And when I say silence, I'm not talking about that apathetic silence where your face screams "Oh, can you finally stop running your mouth and leave me alone? Please? I can't wait for you to shut up."

When I say silence, I mean a very attentive silence that lets the other person know that you're all ears; interested, engaged and responsive. Here's a few tips on how to be a better silent listener:

  • Keep eye contact. Make sure you're not staring at them because that just feels creepy. Occasionally you can break eye contact but for the most part, look at them as they speak. 
  • Return their facial expressions. Most of the time this comes naturally but if you're feeling very anxious during the conversation, severe stress might distract your attention and magnetize it to the discomfort of the situation. And when that happens, it will show on your face and that will break rapport. So as a rule of thumb, try to at least smile back whenever someone shows their pearly whites while they're talking to you. Few things are as awkward as when your friendly smile cannot penetrate the poker face of another. 
  • React to what they're saying but try not to interrupt them. You can often express yourself in subtle non-verbal ways just as well, such as by raising your eyebrows to convey skepticism or by opening your eyes wide open to express surprise, etc. 

#2 Ask Questions

Couple having dinner

If talking to strangers makes you feel nervous and confused, don't worry, there's a smart trick you can use to penetrate the awkward silence that might ensue. 

After all, a conversation is not just about how you can produce a witty comeback or an eloquent reply to impress someone. Oftentimes it gets you further if you express your genuine interest in your partner and pay attention to their story.

And a great way to do that is to ask questions about what they've said. It not only shows them that you're paying attention to their story, but also that you want to hear more. And that's very flattering. 

Just imagine, wouldn't you be flattered if your conversation partner would keep picking your brain with passionate questions instead of sitting there in front of you staring at you with glassy eyes? 

#3 Seek Common Ground


So you're having a conversation with a stranger and it's coming along nicely. The two of you are in rapport and you've managed to keep the conversation flowing by asking questions every now and then and paying attention to them.

Sooner or later your partner will come up with a topic that you'll be passionate about, too. You might need to be patient but after a couple of minutes, you'll hopefully find a common hobby, a common interest or an opinion you two share.

But hold your horses! That doesn't mean that you're free to take the spotlight and hog it to yourself while your conversation partner gets to listen to all the things you have to say about the subject.

Make sure that the conversation is not only about you. Try to get to know your partner a little better and let them speak, too. And for that you need to be a good listener.

Also, if you manage to find a few common points of interest, that's great because that means that you'll have a reason to get in touch later, talk on the phone or invite them to hang out with you and do something that you both are interested in.

#4 Think about Similar Stories You Have


While you're giving your utmost attention to your partner and occasionally pry them for more with a few questions, you'll need to be thinking about what kind of similar experiences you personally had in the past. 

Think about what kind of similar things have happened to you in your lifetime and make lots of mental notes. And the next time that awkward silence rears its ugly head, you can bring up your personal story to keep the conversation going. 

As an added bonus, this gives authenticity to your compassion as it proves that you have experienced something similar and so you know what you're talking about.

For example, let's say someone is telling you about how their cat died a few days ago and that they're still very sad about the loss of their furry friend. Before you try to comfort the person, it's a good idea to tell them about how you felt when your dog died a couple of years ago. 

And then you might want to try to help  by sharing your best advice on how to deal with the loss of a pet.

#5 Recap

If you're really running out of ideas of what to say, you can always choose to recap what the other person has been saying. 

You might begin with something like:

"Just to make sure that I understand correctly..."

And then you go ahead and summarize the gist of what they've been telling you. This is not only an authentic display that you've been paying attention but it also tells the other person that it's important to you to have a good understanding of what they're telling you. 

And that's a very kind and flattering gesture.

Next Steps

The 5 tips that I've shared with you above will help you eliminate that awkward silence that happens when a conversation has run dry and both parties feel clueless as to what to say.

And while following these tips will not paint your tongue silver, it will make you a good listener and a pleasant company. And that's kind of a big deal, especially if you're shy.

And as soon as you build some muscle memory in social interactions, you'll find that you'll start tweaking these tips intuitively to match your unique personality.


Man with a mask

If conversations make you feel nervous and uncomfortable, try not to worry too much about it. That's natural. Everybody feels a little bit anxious before they walk up to a stranger and say hi. Who wouldn't feel butterflies in their stomach standing face to face with an attractive member of the opposite sex trying to strike up a conversation?

Some label this feeling anxiety while others call it excitement. 

For some people, it's a strong fear that grips at their stomach ever more fiercely as they're approaching the conversation. For others, it's a barely audible tiny whisper in their ears that they've learned to completely ignore.

Epictetus, the Greek philosopher said a very long time ago that

"We have two ears and one mouth so that we can listen twice as much as we speak."

The key to successful communication is definitely the ability to silently observe and listen while we hand over the spotlight to the other person and let them express themselves freely, uninterrupted. In fact, that alone is sometimes enough to avoid any awkward silence at all.

And for the better or worse, the subtle art of listening to someone silently while observing their every gesture and display of emotion is second nature to shy people. 

Since we care a lot about what people think about us and have a strong desire to meet other people's expectations, being a an attentive, observant listener comes easily. 

Shy people that struggle with social anxiety tend to be incredibly sensitive at heart. But it's this sensitivity that will become your biggest ally during conversations because it's exactly what you need for empathy and compassion - the two key personality traits in any conversation.

In fact, chances are that you are a wonderful conversation partner, you just don't realize it. Since you possess the two most important personality traits needed to make it work, all that's left for you to do is muster your courage and seek out social situations where you can hone your conversational skills to perfection. 

Let me know what it is that you want to read about next time and I promise I'll cover it as soon as I can. And if you have any questions about the post or anything to add, feel free to leave a comment below! :)

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