5 Ways To Keep a Conversation From Coming To a Dead-end Standstill

By Melissa Chu

November 21, 2018   •   Fact checked by Dumb Little Man

We’ve all been there at some point.

You’re nodding along as the other person talks to you about something. She might be an acquaintance you bumped into or someone you’ve met for the first time. And as the other person finishes talking, she waits for you to say something. Then, it happens.

The deadly, awkward silence.

It reminds us that we’re not very comfortable with the other person we’re chatting to and it leave us with a dreadful feeling that we’re not as socially smooth as we ought to be.

All is not lost, though.

There’s this woman I know. Whenever she laughs, it seems to light up the room. Everyone flocks around and listens to her whenever she has something to say.

With such superpowers, it seems someone like that would be intimidating to speak with one-on-one. It’s actually the opposite: she makes you feel like you’re the only person in the world and the two of you are best friends.

Now, it might seem like this is something that someone is just naturally good at. However, I believe that with some practice, we can all get better at conversations.

Why It’s Important To Keep Conversations Going

talking about insecurities

If you sometimes feel uncomfortable speaking with strangers or
acquaintances, it can feel easier to just say “Gotta go!” and scurry off. But there are a number of reasons why keeping a conversation going can benefit you.

Learn something new. Speaking with someone we’re unfamiliar with can bring fresh insights. When people share their stories and experiences, it can make us think about our own lives and actions. By keeping the conversation going, you can dig deeper and create a more insightful discussion.
You might make a friend. Every friendship needs to start off somewhere. Think about your closest friends. They probably didn’t start off being close friends with you but over time, you both made an effort to get to know each other better and create a sense of comfort around one another.
Bring new opportunities into your life. It’s true: the more we put ourselves out there, the more the universe throws back at us. In order to get more experiences and opportunities though, this means taking ourselves out of our comfort zone. You never know what someone can bring into your life: advice, opportunities or new connections. At the very least, keeping the conversation going makes for good practice.

How to Keep Conversations Going

1. Pluck up details and expand on them

One of the best ways you can make a conversation transition seamlessly from one topic to another is to subtly shift the conversation so that the topic is still relevant, but fresh.

For example, if the two of you are talking about your living arrangements and the other person complains about their cat leaving fur on the carpet, you can then move towards talking about cats and pets in general. This can include talking about your own pets or asking the other person on what it’s like for them to have a pet at home.

Even if the other individual speaks endlessly on one topic but just briefly mentions something else, you can use this to shift to a different topic. Doing so brings about more conversation in an unsurprising manner because the other person mentioned it first.

2. Ask about them

To each person, they are the center of their own universe. Every day, they focus on their hopes, dreams, and fears. If you can tap into these and get the other person expressing how they feel towards you, it’ll not only keep the conversation going, but it’ll allow them to feel a deeper sense of connection with you.

Shortly after graduating from university, someone I met asked me asked me what my plans were for the future. When I replied where I was working, he didn’t just stop there. He proceeded to ask about what I hoped to do someday and empathized by sharing his own experiences. It felt like he was genuinely interested in knowing more, yet understanding at the same time.

Asking something personal doesn’t have to invade on someone’s privacy. Leave the question open-ended so the person can respond with as much information as they like.

For example, “What are you hoping to do after you finish your degree?” is better than, “Are you going to work in a law firm afterwards?”

The first question leaves it up to the other person to decide how to respond, while the second one isn’t much of a conversation starter. It could even be seen as judgmental if said in the wrong tone.

3. Make observations about your surroundings

You might have just introduced yourselves to one another with a series of quick pleasantries but now, the conversation is coming to a lull. What should you do now?

Why, make an observation about something nearby of course!

talk to somebody

One time, a stranger said “hello” to me. At that point, I introduced myself as well. Looking around, I noticed that it was pouring rain outside and made a comment about the poor weather. We then used this as a jumping point to talk about what we did earlier in the day because it was raining.

You can make a comment about the weather, the food or compliment something the other person is wearing. The conversation doesn’t have to simply be about that one thing, but can be used as a springboard for related topics.

4. Bring in a third party

Introducing a third person into the mix is one of my favorite things to do to keep a conversation going. Let’s face it: sometimes it can be tiring to keep on a conversation. Bringing in another person can mean introducing two new people to each other and allowing them to talk while you contribute once in awhile.

And if the two of them really hit it off, it makes for an easy escape if you want to go do something else.

5. Share, then ask for feedback

Talking about yourself requires a delicate balance. The other person likely will want to know something about you, but you don’t want to bore the other person by making the entire conversation about yourself.

What you can do is to share your own experiences and at the end, ask the other person what their opinions are. If the other person asks you if you’re traveling anywhere soon, you can briefly tell them your plans. Then, ask them if they have any recommendations for your trip.

In Conclusion

The next time you meet someone, try doing one of these things to keep the conversation going and see what happens. Chatting with someone new can be nerve-wracking, but you’ll never know the stories and experiences that will come out of it.

What’s one of the most interesting conversations you’ve had with someone?
Share your stories below.

Melissa Chu

Melissa Chu helps people get productive and develop good work habits. You can download the free guide on how to set and achieve your goals.

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