21 Telling Questions to Ask on a First Date

Going on a first date is thrilling, scary, exciting and full of potential. First dates are a little different these days too, as more often than not you’ll have chatted with your date a bit on an app or by text before you meet up. 

This is great as you’re not going in not knowing what to expect - you already know their views on dogs, what they do for a living and where they live, most likely. But this can mean that you lose a bit of that initial ice-breaking conversation. We’ve pulled together 21 questions you should ask on a first date to help you truly get to know the person you’re on a date with - and decide whether they’re worthy of a second date!

Don’t go firing these off interview style, as you might scare them off, but pick a few to work into your conversation. These first date ice breakers are ideal for avoiding awkward silences and for figuring out if this person is right for you - they’re also not just for first dates. Some of these questions are super fun, so even if you’re in a long-term relationship, it doesn’t mean you can’t ask your partner some of these questions on your next date night. 

21 Ice-Breaker Questions to Ask on a First Date

1. What’s the Worst Chat-Up Line You’ve Ever Heard?

This is the perfect ice-breaker for a first date. As you’re both single and dating, you’ll definitely have your fair share of horrors to compare, so this is a nice, no-pressure question that you can tailor, especially if you met via a dating app, to really get the conversation going.

2. If You Could Go Anywhere in the World Right Now, Where Would You Go & Why?

This is a key question to ask on a first date - it sounds casual and like you’re interested in their favourite destination, which of course you are, but it also gives you a clue to compatibility. If they say ‘oh, trekking in the Himalayas for sure,’ and you’re more margaritas in Marbella, then you might have a future of separate holidays…

3. What’s Your Favourite Memory?

This question will give you real insight into what’s important to them - depending on whether it’s focused around their family, friends, favourite football club… you get the picture.

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4. What’s Something You’re Really Proud Of?

At the risk of sounding a little bit job interview-y, this is a great question as again it’ll tell you what’s important to your date and what they truly value. 

5. What’s Your Most Hated Food?

This a fun question and will also give you a bit of insight into compatibility - for example, if they say they can’t stand any kind of sauce, and you love to cook up a storm, you might have some issues ahead. However, if you’re both a big fan of a roast dinner, you know you’ve got some cosy Sundays ahead of you. 

Also, by asking what a person likes and doesn’t like to eat, you can also discover cultural, religious and ethical beliefs and assess if they line up with your own. There’s a lot to this innocent little question!

6. What Did You Want to Be When You Were Growing Up?

Another fun-sounding question that actually gives away a lot - if they wanted to do the exact thing they’re doing now, you can assume they’re very driven and determined, and know what they want. If they wanted to do something unusual, you can see their creative side and if they’re a bit of a dreamer.

7. Does That Relate to What You Do Now?

For example - maybe they wanted to be superhero, but now they’re a firefighter. Or perhaps the one-time would-be fashion designer is now a fashion buyer for a brand. Asking them to think how their childhood dream compares to their life now will give them a chance to talk about themselves, and can allow for a bit of humour too.

8. What’s Your Favourite Book/TV Show/Film?

You can tailor this question to be around what you’re most interested in, so you can see how much their tastes align with yours. If you love the same things, you’re off onto a whole new conversation about why you love it!

9. Who Would Play You in a Movie of Your Life?

You can see how much or little a person thinks of themselves by how they answer this question - and how great their sense of humour is. 

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10. What’s the Best Gift You’ve Ever Been Given?

Asking this gives you insight into what they truly value, and their answer will be one to bank, should you ever need to get them a gift in the future…

11. What’s the Best Gift You’ve Ever Given?

This question will allow them to demonstrate how generous they are...or not. If you’re someone who puts a lot of value on thoughtful gifts and likes surprise presents, this is one to ask to see if they would please or disappoint you in that respect. 

12. What’s On Your Bucket List?

Whether they call it that or not, everyone has a bucket list of sorts. Finding out what their goals, dreams and biggest plans are can tell you a lot about who they are as a person, as well as if you have a future that aligns with theirs. 

13. What’s the Most Interesting Fact You Know?

Not only is this a fun question, but you may also learn something from it. People love to teach others something new and to feel knowledgeable, so by asking your date this question, you’re giving them that opportunity, which will create a positive feeling for them. 

14. What Was the First Concert or Gig You Ever Went To?

Along with the first CD you ever bought (or track you ever downloaded, if we’re going all Gen Z about it), this question opens up the possibility of a bit of cringe, a bit of humour and a bit of playfulness. Maybe it was Steps at Party in the Park, and that’s actually something to be proud of, thanks. They are cultural icons. 

15. Tell Me About the Best Day of Your Life?

This will give you insight into their values, but also a chance to see them light up as they describe their favourite ever day - and you’ll get to do the same if they ask you!

16. What’s Your Hidden Talent?

Everyone has a hidden talent, and some of them are quite entertaining. Ask this question to give your date a chance to surprise you, but make sure you’ve got your talent ready to demonstrate too. 

17. How Would Your Friends Describe You?

This will encourage them to be a bit more open about themselves, and allow you to see how their friends see them. You’ll get to see what ‘role’ they play in their friendship group - and lead into a conversation about who they are friends with and why. 

18. What’s Your Perfect Weekend?

This question will give you perfect insight into your potential compatibility. If you love getting out for a walk and hate to waste time lying in bed, but they love a lie in and don’t go out until the evening, there might be issues there. 

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19. What’s Your Signature Dish?

If food is important to you, this is a big question to ask! You’ll also be able to flirtatiously suggest they could make it for you, if you feel like you’d like that - or make a mental note to never allow them near your kitchen...

20. Where Do You See Yourself in Five Years' Time?

We are veering a bit into recruiter mode here, but hear us out. If you dream of having kids and a big wedding in your future, you ideally want to date someone who sees their life going the same way. Asking this question is a kind of open-ended way of assessing whether they want the same or similar things to you - and it's a bit more low-key than blurting out 'do you want to get married?!', which is a no-no for date number one. 

21. What’s the Most Interesting Fact About You?

Okay, this one is pure job interview, we know. But there’s a reason why it’s a great question! It allows you to learn so much about another person in a way that wouldn’t necessarily come up in normal conversation, and despite the frequent groans about it, everyone loves to share an anecdote that displays them in a cool light. Just be sure to have your own super-interesting fact lined up to share asl well!

Now you know what to talk about on your first date, make sure you read up on these awesome 56 first date ideas to suit every budget - it’s going to be your best date ever, we know it!