5 Interesting Questions to Ask Someone You’ve Just Met

5 Interesting Questions to Ask Someone You’ve Just Met

This is a guest post by Jacob!

Jacob is an English teacher who was born in Canada but presently lives in Korea. These days he spends his time online helping people become more confident speaking English by presenting English language lessons that look at how English is used in culture, art, and society. Follow him on his  YouTube Channel


Has something like this ever happened to you?

Yesterday I was out with two people. One of them was a close friend, Tiesha. The other person was Tiesha’s friend, Sophia, who I was meeting for the first time. The three of us had just sat down for dinner, when Tiesha excused herself and left for the washroom.

Sophia and I smiled at each other awkwardly. Our smiles seemed to acknowledge what was happening: “Now we have to make small talk until she gets back from the washroom.”

Meeting new people can feel uncomfortable, even if you both speak the same language perfectly. Of course, if you’re speaking with a native English speaker while trying to learn English yourself—well, it doesn’t make things any easier...

So what can you say in English in a situation like this? The following five questions are my favorites to use when I’ve just met someone for the first time:

1. How do you and __________ know each other?

This question works great if you’re in a situation like I was in yesterday. What’s nice about it is it helps bridge the gap between you and the person you’re meeting. The question also opens the door for more things to talk about.

This was actually the first question I asked Sophia after Tiesha left to the washroom. The conversation went like this:

Me: So how do you and Tiesha know each other?

Sophia: We worked together on a summer camp a few years ago.

Me: Oh, yeah! Tiesha’s told me all about that summer camp. I’ve heard it was quite wild.

After that we started talking about her experience working at a summer camp, and the conversation moved forward from there.


2. What do you do to keep life from getting boring?

You’ll likely make the other person smile with this question. It is a cute/more interesting way of asking, “What are your hobbies?” Maybe the person you’re speaking with will start telling you about their job; maybe they will tell you about a project they’re working on for fun. Who knows?

As with all of these questions, you can keep the conversation going by asking more questions and allowing the other person to tell you more about his or her self.

Example dialogue:

You: What do you do to keep life from getting boring?

Person A: Well, I’m a Math teacher—so that takes up a lot of my time.

You: Oh, really? What do you like about teaching?


3. What’s your story?

This is question is very open-ended. It invites the person with whom you’re speaking to tell a story about themselves. And it’s always interesting to hear how other people tell their own stories.

Example dialogue:

You: So, Stacy, what’s your story?

Stacy: Hmmm, well, I grew up in Chicago and went to college in California. My major was political science. And, what else? I love to travel. I actually just got back from a trip to Peru!  

You: Oh, yeah? I’ve never been to Peru. What was the best part of the trip?


4. What are you passionate about?

People love to talk about things that they are interested in. Sounds obvious, right? So why not ask the person you’re speaking with to tell you what they’re passionate about? Maybe the two of you have some common interests that you could discover. At the very least you’ll learn about what the person with whom you’re speaking REALLY loves to do.

Example dialogue:

You: What are you passionate about?

Person A: I play the guitar, and I love writing music.

You: Very cool. And what do you write about?


5. What are you most proud of?

I WOULD NOT ask this question until the conversation has progressed a little bit, as it would probably sound a little weird to ask this right away. But, a little deeper into the conversation, it works great.

What’s nice about this question is that it invites the person you’re speaking with to think about happy things—things that they did that they are proud of. And people love talking about things that make them happy. It is also fascinating to watch other people think about all of the things they’ve done and choose only ONE that they are most proud of.

Example dialogue:

You: So tell me, if you had to choose one thing, what are you most proud of?

Person A: Wow…(takes time to think)…I’d probably say I’m most proud of travelling through Asia by myself.

You: Really? Why do you say that?

Jacob + I also had a live lesson talking about this topic.  Watch the replay of our live lesson below


Here’s one thing to keep in mind:  

People love to talk about themselves.

Some people feel like they have to carry the conversation when meeting someone for the first time. And if this were true, it would be bad news for someone who isn’t confident speaking English. Luckily, it’s not true! Remember, people love to talk about themselves (or things they’re interested in), and they will if you give them the chance to.

These five questions should help make meeting new people less uncomfortable and more interesting for both you and the other person. And if you’d like to know more ways to improve as an English speaker, there is a free eBook (“4 Things You Must Do To Get Better At Speaking English”) on my website