Ask These Simple Questions To Keep a Conversation Going

Have you ever wondered how you could keep a conversation going? Or what you could do to move one beyond small talk?

If so, you’re not alone! As an English learning platform, we’ve helped many students who were in the same boat as you.

Below, we’ve organized the most common kinds of questions you can ask during an English conversation to keep it going.

Ask “What About You?”

If you don’t already use “What about you?” ("What about you?"), add it to your conversation toolbox now! It’s one of the easiest ways to keep a conversation going. 

For example, if your conversation partner asks if you like spicy food, you can answer the question and then ask them the same thing with “What about you?”:

In a conversation with more than two people, it’s also a good way to bring the third or fourth person into the conversation.

Ask “Why?”

Asking someone for reasons is a good way to expand the conversation. However, asking “why” can sometimes be too direct.

So it’s often better to use one of the following:

  • Why is that?
  • How come?

You can think of “how come?” as a shorter form of “how did you come to that opinion?” or “how did you reach that opinion?”

See how it’s used in the following dialogue:

Notice that by saying “How come?” Zach means, “Why not?” or “Why don’t you like alcohol?”

Ask “How?”

In addition to asking “why,” you can also ask questions that start with “how.” Why and How questions are open-ended. This makes them better at “opening up” a conversation than Who, What, Where, and When questions.

Here are some How questions you can ask:

  • How did you get into this (new hobby)?
  • How did you decide to (join this company)?
  • How did you reach that conclusion?
  • How so?

This last one is interesting. “How so?” means “How is it so?” “So” replaces an adjective. For example, if your brother tells you your hair looks weird, you can say, “How so?” to mean “How is it weird?”

Here’s another example:

Nina’s “How so?” means “How was it nice?”

Ask “What do you think?”

Another great way to develop a conversation is to ask someone their opinion on something. Here are three ways you can do this!

  • What do you think about this?
  • How do you feel about this?
  • What are your thoughts on this? 

“This” in the questions above can be replaced with whatever you want to ask about. For example, “What do you think about the new law?”

Keep in mind that “think” as a verb is used with “about”: “What do you think about this?” But the noun form, “thought” is used with “on”: What are your thoughts on this?”

Ask “So What?”

“So what?” means, “So why does that matter?” However, don’t use this phrase with everyone, because it can seem rude!

Instead, it’s usually safer to use one of the following:

  • What do you mean by that?
  • Why does that matter?
  • How does that relate to the topic at hand?

However, if you want to soften these questions more, you can use the phrase, “Sorry, but ….” For example:

  • Sorry, but what do you mean by that?
  • Sorry, but why does that matter?
  • Sorry, but how does that relate to the topic at hand?

And if you’re in a more delicate situation and need to soften these even more, you can use phrases like “I’m not sure ...” or “I’m not sure I understand ….” For example:

  • Sorry, but I’m not sure what you mean by that. 
  • Sorry, but I’m not sure I understand why that matters.
  • Sorry, but I’m not sure I understand how that’s related (to the topic at hand).

Ask “What if?”

Hypothetical questions usually ask “what” you might do “if” something happened. That’s why they’re also called “What if” questions. While they don’t have to start with “What if …,” many do include “if” statements:

Depending on the topic you're discussing, you can ask about hypothetical situations, such as:

  • What if they gave you a raise? Would you still want to quit?
  • What if your friend apologized to you? Would you forgive her?
  • If you were the one planning the event, what would you do differently?

You can review the grammar for making such sentences here.

“Tell Me More!”

Finally, “if all else fails,” ask the person to tell you more about something. 

  • Interesting. Tell me more about this!
  • Could you tell me more about that?
  • I’d love to hear more about that.

You can see “tell me more” used at the beginning of this interview: 

Time to Practice!

So now you know that instead of Who, What, Where, and When, you’ll want to use more How, Why, and What If questions to open up your English conversations.

But a lot of us are not naturally good at conversations, so we need practice.

You can start by using the questions in this post to write a conversation. Or think about a recent conversation you had. How could you use these questions to make it better?

And for the best results, practice using them in actual conversations! 

If you’re looking for a safe environment to do this, our tutors are here for you 24/7 and have helped hundreds of thousands of students improve their conversation skills, whether for business or personal life! To help you get started, your first session is on us.