10 Conversation Starters That Are Perfect For Your Kopi Date

Imagine this. You’re sitting down on your first date. You’ve got sweaty palms and sweat running down your back.

You’re looking at your date then your mind goes completely blank.

You start panicking. You wonder; What do I say? Should I ask about their day? Maybe the weather! Or wait for them to speak first altogether?

Well first let us just say you’re not the only one to be stumped for a conversation on a first date.

We’ve all been there. Often when you’re meeting someone for the first time your thoughts feel scattered. And try as you may, you feel like you can’t just seem to get a hold of them. Well, don’t worry! If you’re lost for words we’ve got just the solution for you to get the ball rolling.

Here are 10 prompts perfect to start a conversation on your first date!

  1. What do you like to do when you’re not working?

This is the perfect question to get your date to talk about themselves. It gives you insight into who they are as a person and is a natural way to lead the conversation off work if you find yourself stuck on the subject.

Furthermore, it gives you a glimpse into their work-life balance which may be important for you to note. And lastly, it’s a lovely way to get your date talking about their hobbies and passions!

2. What’s something you’re most proud of?

This is one of our favourite ways to break the ice. It’s a question that is both substantial and fun! Asking this will help you see the things they’ve worked hard on.

And you’ll also be able to tell a little bit about what they value! All in all, this is an all-rounded question that can be interjected into the conversation anytime you see fit.

3. Would you rather abandon everyone you know or have everyone forget who you are?

This is a great question that is barrels of fun with just the right amount of depth! You’re sure to launch into an interesting conversation about what it means to be remembered and what it means to abandon.

And no matter their answer you’re sure to get a glimpse of who they are as a person and what they value most when it comes to relationships.

4. If you could be one person for a day who would you choose to be?

This is a fun way to get to know a person’s goals. Often the person they chose, represents their ideal self in some way.

Some follow up questions to this query would be:

(a) Is that the future you’re working towards?

So you get to go into further details about their goals and aspirations.

(b) Who would you never want to be for a day?

Although difficult to answer, this question is a sure-fire way to get a deeper look into their life principles, personalities and values.

5. If you were one of the few people left on earth, who would you hope to be there with you?

This question may seem heavy however it’s a fun way to get to know who your date cares for the most without having to directly ask them that.

You get to see who they find special in their lives and who they couldn’t live without. We also love this question because it’s a great segway into the family and friends they hold.

You could learn so much about your date’s background just from this simple question.

6. What’s something your current self would tell your 12-yr old self?

A person’s past doesn’t necessarily affect their future, but it can show you how much they’ve grown.

This is a great prompt that could lead to a deep conversation about how much — or how little — the past had affected your date.

7. If someone were to write a book about your life, what would it look like?

This is a great question to get a rundown of your dates life without asking it directly. It also poses an interesting setting where your date gets to highlight points of their life they think others would enjoy.

And most importantly it's a fun question that also prompts deep conversation and raw responses.

8. How would your best friend describe you?

When we talk about ourselves, we often talk about the version of ourselves we want to be rather than who we truly are. This prompt allows your date to put themselves in the shoes of someone else. And the shoes of someone who knows them best at that.

The result is a genuine description of who they are as a person and what makes them tick.

9. If you run a company, what’s the one thing you’d be sure to do for your employees?

With this scenario, you’ll be able to tell what your dates principles are.

For example, in your dates imaginative company, they could opt for paid maternity leave for both parents regardless of gender.

From the answer above you could gather that your date favours inclusivity in their life and you could then ask them more questions about it if that is something you favour as well.

It’s a great question that will launch the conversation into social views.

10. What’s one piece of wisdom you’d give future generations?

This question may require some imagination and pondering but we guarantee it will elicit some fun responses. You and your date can have fun with this question and steer the conversation into what both of you imagine what the future looks like!

Furthermore, if you want to get personal with this question you can by asking what their own future looks like 10+ years into the future!

These conversation starters are a way for you to start speaking with your date but you don’t have to feel restricted by them! And if you’re worried you can’t remember these prompts, don’t! Cause we’ve got you covered! All our dates come with our Experience Kits that have more interesting conversation starters and activities for you to do.

With these kits, you can say goodbye to first date jitters and focus on connecting with the person you’re with!

Kopi Date is a unique dating experience where you’ll get to learn more about yourself, what you need in a partner and more!

We’d love for you to check us out. And finally, we’d love to hear what you think of the prompts above! Do you have any to share? Most importantly of all, we want you to know that the best conversations on a first date, are the ones where you’re yourself. Express what you want and show your date how dazzling you really are.


Kopi Date is a startup that curates thoughtful 1:1 coffee dates at unique spaces in Singapore.

We offer the easiest, most authentic, and stress-free way to meet interesting people. With us, it’s all about dating with intention ☕️ Plus, you’ll meet amazing individuals.

Leave the work to us and take swiping off your to-do list!

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