Starting a conversation is half the work.
But how do you keep the conversation going?
In this article, I will share a few helpful words and phrases to help you avoid awkward silence and boredom in conversations.
Get them to elaborate
By asking for elaboration, you’re giving them more space to express themselves, which often leads to a deeper conversation. Here are my favorite phrases:
Oh?
Use this whenever you find what they said interesting. For example:
"Man, what a crazy day." "Oh?" "Yeah, let me tell you what happened…"
Other variations include:
- Hmm?
- Why?
- Really?
Tell me more…
Use this when you want them to elaborate — when you feel that they have more to share. For example:
"Man, I had the best trip ever."
"Tell me more!"
Other variations include:
- Would you like to share more?
- Are you comfortable sharing more? (if it’s a particularly personal topic)
- I demand details! (if you want to be playful)
- Spill the beans! (again, if you want to be playful)
Could you say that again?
Use this when you didn’t catch their words… or when you get distracted (it happens!) You could also say:
- Could you repeat that?
- Could you say that in a different way?
Now, if your mind went blank, here are four tips to help you refocus on the conversation:
4 things to do if your mind goes blank in conversations
What does <word/phrase> mean?
Use this if you heard them clearly, but you don’t understand a specific word or phrase.
"Did you want to have some poulet?" "What does poulet mean?" "Ah, chicken. Sorry."
Wow!?
Use this to express disbelief or shock at what they’re saying. For example…
"I saw a bunch of UFOs in my bedroom last night." "Wow!?"
Other variations include:
- For real?
- Oh really?
- Wait… what!?
- WTF/WTH
Repeat what they said
Repeating a particular word or phrase that they used is often enough to get them to explain. Here’s an example:
"The party will be SO wild!! You have no idea man" "Wild?" "Oh man, you didn't know that they are gonna dance on the streets?"
Confirm what you just heard
Apart from asking the right questions, paraphrasing is one of my favorite conversation tools, as it helps me a) confirm what they said b) show that I’m really listening.
In a research study, participants felt better when the interviewer paraphrased what they shared about a conflict.
Paraphrasing is essentially repeating what they said, but in your own words. Here are a few ways to paraphrase:
- So what you’re saying is…
- It sounds like you’re saying…
- If I understand you correctly…
- What I’m hearing is…
- I might be wrong, but…
- Tell me if I’m wrong, but…
Here’s an example of what good paraphrasing sounds like:
"Most people don't understand how tough social anxiety can be. You can't just "get over it". You know?"
"Yeah. If I understand you correctly, most people don't see the real challenges of having social anxiety like you do."
"Exactly!"
Acknowledge what they’re saying
As human beings, we all crave to be understood and to “feel felt”, as a former collaborator, Dr. Mark Goulston, would say. In fact, research shows that you can make someone feel less angry by simply validating how they feel!
Here are a few ways to acknowledge what someone is thinking and feeling:
Right
This is the verbal version of a nod: a simple confirmation of what they’re saying. This is helpful to show that you’re paying attention. (I’d do this sparingly so that it doesn’t interrupt their talking.)
Other variations include:
- Yeah
- Got it
- Gotcha (more informal)
That sounds <emotion>
Use this when they’re sharing something particularly emotional. For example:
"Man, I'm not sure how I can make new friends. I'm so lonely…" "That does sound tough. How can I help?"
Other variations include:
- That must feel…
- I can’t imagine how <emotion> that is for you…
If you aren’t sure about what they’re feeling, you can always start with a paraphrase: “It sounds like you’re feeling <emotion>?”
I can see that
Use this when someone is sharing an opinion and you understand why they think or feel that way. This is helpful even if you don’t necessarily agree with them. For example:
"He's so annoying when he talks."
"Yeah, I can see that…"
Other variations include:
- I can see where you’re coming from
- I can see why you might think/feel that way
I really resonate with that
Use this when you want to express strong agreement/appreciation of what they said. For example:
"You don't need to be a natural to be great in conversations." "I really resonate with that… that's why I created Deeper Conversations!"
Oops, that’s just me talking to myself 😛 Anyway, other variations include:
- Absolutely!
- Hell yeah!
- That resonated
- I can’t agree more
- 100%
I can relate
Use this when someone is expressing a personal opinion/experience and when you have a similar opinion/experience. For example:
"I wish I could go back to the past…so many regrets." "I can relate!"
Other variations include:
- That sounds like me
- I’m like that too
- I’m the same!
Display a positive reaction
Reacting positively to what someone said — especially if it’s a positive event they experienced — is more powerful than you think.
Research calls this “capitalization”, and multiple studies show that it’s a powerful predictor of your relationship success. (I learned about this by reading Stronger Than You Think by Dr. Gary Lewandoski – highly recommended!)
Here are a few of the many ways to react positively:
- Wow!
- Congrats!
- That’s incredible.
- That’s so wonderful.
- I’m so proud of you.
- You’re killing it!
- You totally deserve the recognition.
Ask their opinion
h/t: Raz Roslan
There will be times when there isn’t really anything that you can build on conversationally. If that’s the case, inject new energy into the conversation by starting a new topic.
Here’s what you could say:
- What do you think about…
- Most people think… what do you think?
- How do you feel about…
- Did you know that…
- Have you heard about… (here are a few other conversation starters to gossip away)
For example:
Did you know that the Beetle was invented by Hitler?
WTF - I did NOT know that. Really?
You could also share your opinion and invite them to share their thoughts. Just say whatever comes to your mind: whether it’s your new favorite cafe, your career transition, or your never-ending fight with the morning snooze.
PS – If you find yourself overthinking about what you should/shouldn’t say, I highly recommend this article of mine: How to stop overthinking conversations (for socially anxious)
Redirect the conversation
What I’ve said so far helps you build the conversation. But what if the conversation needs to take a new direction?
For example, they keep talking about the same things over and over, or you just find the topic boring (despite your best attempts to stay engaged.)
Rather than playing “conversation victim” and suffering in silence, you have the choice to divert the conversation. First, gently acknowledge what they’re saying. Then, sneak in one of the redirects…
- What you said about [topic X] reminds me of [topic Y]…
- That sounds like [topic Y], because…
- Speaking of which… (jump straight into another topic)
- By the way, I was curious about what you said earlier…
- I hate to interrupt, but could we talk about something else? (this might sound confrontational, but it’s helpful if they can’t seem to stop talking)
Disagree with them (calmly and gently!)
While it might feel uncomfortable to disagree with someone, disagreement — when done right — helps you see each other’s perspectives and build a deeper relationship.
As Stanford professors Carole Robin and David Bradford wrote in their book, Connect, conflict can be a door to deeper connection and love.
Here are a few ways to disagree while still being respectful of their opinion:
- Another way to look at this is…
- Here’s another perspective on this…
- I appreciate your perspective. Here’s my perspective on this…
- I can see how you would think that way. Here’s how I see it…
- I can see where you’re coming from. At the same time…
(Now, if the conversation turns sour, here’s how to end the conversation without being rude.)
What if there’s awkward silence?
While the phrases I recommended will help you minimize awkward silence in conversations, there will still be moments when you run out of things to talk about. And that’s completely normal!
Here are a few ideas to keep the conversation going regardless:
How to keep a conversation going when you don’t know what to say
What to say at the end of a conversation
All conversations come to an end. You don’t need to end with the grace of a ballerina: all you need is a go-to phrase or two to wrap things up. Here’s a list of resources depending on your situation:
- 12 simple phrases to end a conversation politely
- How to end a conversation with a friend (without being awkward)
- 5 ways to end a phone call without being awkward
- 4 ways to end a boring conversation politely
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