25 Incredible Conversation Starter Questions to Use in Any Situation

We’ve all been there. Stood next to someone, smiling politely, trying to avoid eye contact, cringing inside at the awkward silence. We wrack our brains for something to talk about, anything to break the tension, but we keep drawing a blank.

It’s uncomfortable when you get into this situation, but there are ways around it. By arming yourself with some great conversation starters, you’ll be in the perfect position to tackle any social situation with ease.

Why is it important to have go-to conversation starters?

There are many reasons you might want to keep a mental file of handy conversation starters to crack open at a moment’s notice.

When faced with a new situation, it can be easy to get overwhelmed. And once that panic sets in, your brain finds it more difficult to string logical thoughts together, making it more challenging to think of ways to start a conversation.

It’s even worse if you suffer from social anxiety. You probably analyse every word that comes out of your mouth and judge yourself for it. Having a prescribed set of conversation starters allows you to feel more in control of the conversation at hand. 

What makes a good conversation starter?

All great conversation starters have a few things in common.

-   They are open-ended

This is important to keep the conversation flowing long after the initial question 

-   They are relevant to the situation

 You wouldn’t ask a guest about divorce statistics at a wedding, would you?

-   They pique interest

Questions that allow you to explore beyond the weather and someone’s job are always hits.

If that all sounds overwhelming, don’t worry, we’ve got you covered. Here are 25 of the best conversation starters to have you confident in any conversation.


Basic conversation starters for the first time meeting someone

The type of questions you ask when meeting someone for the first time will be dependent on how confident you are feeling.

These questions are great fail-safes for when you are trying to feel a person out and gauge how receptive they are to the conversation. 

  1. How do you know the host? 

Simple starter here. Working out how you are connected to the person or organisation in charge of the event or situation allows you to find common ground with the person you are talking to.

  1. Do you know a lot of people here?

Similar to the question above, this question helps you find something in common quickly by working out what connections you share.

  1. What are you going to do this weekend? 

A straightforward question, this is an easy way to discover various hobbies of the person you are talking to. In addition, this gives you a jump-off point to further the conversation. For example, if they say they have nothing planned, try asking what they would do on a typical weekend or their ideal weekend.

  1. Are you having a good time?

Yes? Great, what are they enjoying most? Do you feel the same way?

No? Why not? Is there anything that would help them enjoy the situation more?

  1. Do you have any pets? What are their names? If not, why not?

We human beings have a strange obsession with our pets. Hey, no judgement! It is what it is. Getting someone to speak about their pets opens a world of conversation avenues. You can also tell a lot about a person by how they talk about their animals.

Conversation starters to get to know someone better

Once you get past the pleasantries, it’s time to explore the conversation a bit further. The goal is to find common ground and potentially make a connection that will result in the beginning of an acquaintanceship, friendship, business relationship or maybe even romance!

  1. What did you do on your last holiday? 

Where did they go? What kind of activities did they do? You will learn a lot about how someone likes to spend their free time by what they choose to do on holiday. You may even find you have the same taste in holiday destinations and activities. Heck, you might also get some great travel inspiration!

  1. Are there any Netflix/Disney+/Television series you would recommend?

While a trivial topic at face value, someone’s preference for film and TV, and the way they talk about it, gives you an idea of what brings them joy and the kind of personality they have.

  1. What’s the last skill you learned?

If you play your cards right, they might even demonstrate it to you!

  1. When was the last time you laughed so hard you cried?

Nothing bonds people better than laughter. When someone recounts a funny story, they’ll probably be laughing as they tell it, and in turn, you’ll probably get the giggles too. Win-win!

  1. What’s the best gift you’ve ever gotten?

This question opens the window into someone’s sentimental side, allowing you to make a deeper connection.


Conversation starters specifically suitable for professional environments that won’t bore you to tears

Some occasions call for the dreaded work talk. But with a little twist, even work can be interesting to talk about! 

  1. If you didn’t have the job you have right now, what would you do and why?

This will let you know how a person feels about their current situation and give you an excellent insight into someone’s career goals. 

  1. What is the most frustrating thing about your job?

Frustration can create an opportunity for good conversation. But, unfortunately, life isn’t always happy, and you would be doing a disservice to yourself to only partake in positive discussions.

  1. What is something people assume about your job that is completely wrong?

This is an inventive way of asking if there is something that people don’t know about them that they’ve always wanted people to understand. 

  1. What was the highlight of your week? 

People love talking about themselves and their accomplishments. So why not indulge them by discussing their recent events? It’ll also signal to you what matters most in their life. Was their highlight work, family, hobbies?

  1. If you had to pick any character from a book, film or TV show who is most similar to you, who would it be and why? 

If you know the character, this gives you more insight into how the other person views themselves in a more understandable way for you.

Conversation starters that go deeper

Want to make a deeper connection? It’s time to ask the bigger questions!

16. Who had the biggest impact on you that shaped who you are today?

In other words, what makes you the person you are today? And, who inspires you? This can easily lead to conversations about childhood and past experiences. 

  1. What is the strangest dream you’ve ever had?

Let’s get personal. What lives in the depths of your imagination? It’s an interesting topic to get into, and one I’m sure a lot of people haven’t been asked before. 

  1. What’s the hardest thing you’ve ever done?

Aka, what is the biggest thing you’ve ever overcome? This gives the person you are talking to an opportunity to celebrate coming through adversity and offers you the chance to celebrate them.


  1. What is a habit you find challenging and want to learn?

We all want to improve something in our lives yet struggle to do so. It’s something we all share in common. So why not talk about it? You might even pick up some tips!

  1. What makes you nervous? 

Why not completely break the ice and see what makes your talking partner nervous? Plus, if you feel nervous, it opens the conversation to discuss that too and will make you feel more comfortable.

Fun conversation starters to keep the party going

Conversation starters don’t have to reveal something insightful about the person you are talking to. It could just be a way to start a fun conversation or activity.

  1. What’s your strangest hidden talent?

Events are always good for party tricks. Get the person to demonstrate their hidden talent, and encourage other people around you to join in.

  1. What is the funniest video you’ve seen on YouTube?

Not only will this provide a good topic to talk about, but you can also watch the video together and share in the laughs.

  1. What’s one interesting thing about yourself that no one really knows?

There’s something fun about sharing a private moment with someone in a crowded place. It will also provide you with more opportunities to get to know each other better. You could even make it into a game like two truths, one lie.

  1. What is the stupidest joke you’ve ever heard?

Knock knock! Who’s there? Just another great way to start a conversation! 

  1. Want to play rock-paper-scissors?

A conversation starter doesn’t have to be all words. Why not invite someone to play a quick game with you? You’ll descend into laughter, and the banter will flow naturally!

With great power comes great responsibility, so use your new gift of the gab wisely!

25 Incredible Conversation Starter Questions to Use in Any Situation

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