How to Keep a Conversation Going?


How to Keep a Conversation Going?

Every time I start a conversation with someone, it normally slows down after the first couple minutes. This then brings us to that awkward silent moment. It doesn’t help when you conjure up something to say, but you eventually return to that awkward silence.

To keep a conversation going, it starts by being a good listener. That doesn’t mean just sitting there as the other person speaks and simply nodding your head like a bobble head. You really need to listen to what they’re saying, how they’re saying it, and if there’s a deeper meaning behind their words.

How to Keep a Conversation Going

When someone says something to you, make a mental note of what’s important to them. So by the time it’s your turn to speak, you can bring up one of their mental notes and dig deeper into that. From there, it’s a repeat game of you picking up certain topics the other person speaks about, and relaying it out to them.

Is that all it takes to make a conversation going?

You will get further than the average person during a conversation, but it won’t do you any good if you only learn about the other person. And even though the person speaking to you will love giving you their life story, they’ll be at a slight disadvantage because you’ll know everything about them as they know nothing about you.

How to Keep a Conversation Going

To make the grounds even to a point they feel comfortable being around you, you need to tell them a few things about yourself. Don’t overload them with useless facts about your life. Just share your own personal experiences that relate to whatever the other person is speaking about.

Think of your own personal thoughts or experiences and combine it with your emotions. This adds to the conversation, making it golden because you’re adding to their values by giving a bit of your own.

The most important thing to remember is to simply pick on the important things that they say. Those important things are usually events triggering their emotions, strange personal experiences, or personal passions that light their eyes.

People love talking about themselves, but they need you to be able to open that gate up for them.

For example, suppose you met someone who said they worked as a salesman in the city. You have 2 conversation routes to head to from that sentence. One route you can take is digging into the job of a salesman. Talk about how his work environment is like. Talk about how he got into that field. Talk about what his true passion is and if he had a dream job. Chances are his dream job wasn’t being a salesman.

Or maybe you don’t care about his life as a salesman. Dig into how he enjoys living in the city. Ask about what he normally does and the great advantages he has for living in close quarters to such lively events. Get an idea of what they like doing on a daily basis. From there, add your own personal experiences and life story to make the conversation lively and entertaining. And if you’re still searching for ways on what to say, check out some tips on How to keep a conversation actually interesting.

How to Keep a Conversation Going

Avoid making the conversation center around you and pay attention to the other person instead. It gives them a chance to relive their past experience through another person’s eyes. It’s almost like re-watching a movie with someone who never seen it before. Just the look in their eyes will make it as if you’ve never seen it before.

The best part is that by the end of the conversation, the other person will be addicted to talking to you. You’ll be the channel that connects their good emotions to their past memories. Whether you talk to a female, male, young or old, everyone is the same in this category.

When someone speaks to you, enlighten their answers and explanations with enthusiasm and interest as if it’s the greatest thing you’ve ever heard. Don’t oversell it because you’ll come off as fake and uninterested.

When the other person laughs, laugh along even if you don’t know what they’re talking about or the punchline of the joke.

When you’re speaking to a crowd of people, especially strangers, ask each one of them a question that relates to the main conversation topic. Get an interest on what everyone enjoys and if they’re too afraid to say too much, act as the example they need. Share your own thoughts and interests and pull them in with stories about your life.

Don’t share too much about yourself, but show that you have much to offer to them and that it’ll be worth investing their own story into the conversation. All that group need is a little push to make the ball rolling. Before you know it, someone else will add to the conversation about their own thoughts, which will then cause another person to do the same.

But always keep that ONE habit that assassinates any conversation:

Avoid the yes or no questions or responses like the plague:

No one like giving those answers just as much as the people who ask those questions. Unless it’s literally a question that requires a yes or no response, not too many people enjoy those short answers because it brings you both to a dead end.

If you ask a yes/no question, you’re pushing someone in a corner because you’re putting them in interview mode. You want them in drunken mode, where they can add much to the conversation effortlessly.

Chances are, you’re going to meet a lot of introverts and people who aren’t talkative. And unless you want to play 20 questions with them before getting somewhere good, dig deeper into the other person interest. If you don’t know what they enjoy doing or have no interest, talk about the environment you’re both in. And if you’re in a boring environment, talk about what’s happening in the world.

How to Keep a Conversation Going?

This also points to you. Don’t give anyone a yes/no response if you actually want the conversation to continue going. If you are forced to give a yes/no response, give the reason why you say that. Add your emotions into that answer so it’ll be easier to keep that conversation going.

And for those interested on ways to enchant anyone you’re speaking to, become familiar with the 10 Laws that Conversationalists use to win people over. It heavily reflects a book titled, How to Win Friends and Influence People to make it easier for anyone to understand the major points.


An Important reminder:

Be aware that despite following these rules, this doesn’t completely eliminate the possibilities of the silent moment. (Say what?) However, it’s important to know that it’s perfectly okay and normal for the awkward silent to appear in a conversation. Suppose you took a walk with someone downtown or sat together in a restaurant for several hours. The idea of maintaining a conversation for that long will be insane and tiresome.

So when you have a few minutes of silence, don’t think it means you lost the other person’s interest. Use that time to recollect your thoughts and take a moment to think to yourself. From there, feel free to add in small comments about what you’re thinking or what you see. The other person is already comfortable with you and don’t need your validation to keep a conversation going.

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And if you’d like some more information on how to master your social skills, a few hot tips to check out are:

Why it’s normal to go out alone, and how it benefits your life

An effective method to never run out of things to talk about

How to Curb Stomp social anxiety

12 Easy Tips to Become a Skilled conversationalist


About Author

Besides being random and dealing with ADHD from time to time, Michael Gregory II is the CEO of the Self Development Workshop. He's traveled to over a dozen countries, counselled a variety of people, and continues furthering his knowledge in self-development, depression, and mastering your happiness. On his lazy days, he enjoy watching people, reading in Starbucks, and speaking to random strangers. (Yeah, he’s weird.)


  1. Great article man I always enjoy the MS Paint illustrations. I learned in psychology that those moments of silence are naturally occurring in conversations with groups of people after several minutes. Some people feel awkward when there’s no conversation but not I!

  2. Thanks so much Andrew! Sorry for the delay in my response. There was like a MONSTER of spam messages I had to fight through lol.

    Thanks for liking the MS Paint illustrations and your encouraging words! You’re awesome!

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