20 Questions To Ask On A First Date That Aren’t Boring

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“So, what do you do in your spare time?”

Heard that one on a first date before? Of course you have!

If you’re fed up with boring questions and want to find out more about who your date really is, we’ve got 20 amazing questions to help you dig a little deeper.

You might have just met, but you’ll spark a great conversation with any of these questions…

1. Where did you grow up?

This one shows that you’re interested in getting to know them! It’ll also give them a chance to open up a little bit more about themselves.

It’s also something they know better than anyone else, so they’ll probably feel quite comfortable talking about it.

2. Where’s the best place you’ve visited? 

Get them talking about travelling – everyone loves travelling, after all! And it gives you the chance to share your favorite place too.

Their answer will reveal a lot about them – are they a jet-setter or a homebody? Are they someone who loves an action-packed adventure, or are they more comfortable sunbathing by the pool in a five-star hotel?

3. What would be your dream breakfast in bed?

This is a cute, playful question. There’s no hidden agenda, but it will get them talking – nobody can hold back when it comes to sharing their fave foods.

That being said, they might hate breakfast in bed and tell you that they prefer to hit the gym at 6am with a protein shake. Do with that what you will!

4. What’s the last movie you watched?

Their answer will tell you a lot and can help you determine how much you have in common.

Maybe they’re a cinema lover who always sees the latest releases, or they love the same niche genre you do.

Either way, you’ll learn a lot about them, and it’s an easy way to make them feel more comfortable around you and ready to open up about themselves.

5. Who was your childhood hero?

Tell them yours first and see what they come up with as their answer. It could be a comic book superhero, your dad, or your favorite teacher from school.

It’s not a typical first-date question, so they’ll probably just be excited to be asked about something new!

It’ll show you a more vulnerable side to them and will probably lead them to sharing something more personal than most first-date questions would do.

Maybe they had a bad upbringing, so dreamt of flying away with Superman, for example – you’ll bond more through sharing these kinds of deeper, more intimate conversations. 

6. What would you do if you won the lottery?

You’ll quickly find out if they’re a real family person (“I’d buy my mum a house”) or if they love big trips (“I’d quit my job and travel the world”) or if they’re super sensible (“I’d put it in my savings account”).

Whatever their answer, it’ll spark a fun conversation about what you would do, all the places you’d like to visit, or how much you love your families.

7. What’s your ideal Sunday?

You’ll find out what they’re interested in by asking this question, and it’s a nice alternative to just “what are your hobbies?”

They might love long walks, lazy brunches, or board games nights. You’ll quickly see what kind of things you have in common and can even cheekily suggest spending a Sunday together doing their favorite things as a future date…

8. How would your best friend describe you?

It’s always fun to see how people respond to this – a lot of people can be their own worst critic, and their friends often have a better, nicer (and more accurate!) view of them.

See what they say, ask about their friends and make an effort to show an interest in their real life!

Some people can put on a bit of a front when it comes to a first date, but this is a good reminder that they have people who like them already, so it might give them a confidence boost and let them be themselves around you.

9. What’s the last book you read?

This is a really good question if you’re the kind of person who loves reading and would like a partner who shares that pastime.

You’ll discover whether they’re an avid reader just like you, or if they’re really into history/ true crime/ fantasy novels.

You can bond over the books you both love, and might even end the date in a bookstore picking out a new novel for each other.

10. What’s your signature dish?

Ask what kind of thing they like cooking and they’ll probably let their guard down a bit.

Most people feel pretty relaxed when they start talking about food – either they love cooking and really enjoy talking about food, or they’re not that fussed and will give you a quick answer.

Either way, you’ll find out a lot about them from their answer! If the date is going well, you can always suggest they make it for you on the second date…

11. How do you spend Friday nights?

If you’re the kind of person who’s always partying, you might not want to date a more reserved person who doesn’t go out much.

Equally, if you don’t drink and prefer a chilled night at home, you might not feel comfortable dating someone who DJs at a club until 3am.

Finding out what their typical Friday night looks like will tell you a lot about their personality and values.

12. What’s your love language?

If they’re not sure what theirs is, it’ll spark an interesting conversation. You can share yours, too, and it’ll give you some good insight into how compatible you’ll be together.

It might be that you both share the same one, or that they hate texting and your love language is ‘Words of Affirmation.’

Consider how well you’d match up together, long-term, but remember to be open-minded. Some people like to present a certain image of themselves on a first date and you might not see the full picture this early on.

They might also love someone who texts back quickly but don’t want to come across as ‘needy’ on the first date.

13. What are you currently binging on Netflix?

Again, this will help you gauge their vibe and will let you know if they’re more into documentaries, reality TV, or – shock, horror – just aren’t a Netflix kind of person.

Or, you might find that you’re watching the same show, which will give you something easy to talk about – there’s no hidden agenda with this question, just genuine interest.

14. What’s your view on *insert current affair*?

Choose something big in the news and ask their opinion on it. It could be politics, climate change, or even celebrity news – whatever you’re most interested in yourself.

If keeping up with politics, for example, is important to you, you’ll soon find out if they feel the same.

While it’s not everything, if it’s an important thing to you, you’d ideally find a partner who shares that same interest.

15. What’s your 2-year plan?

This isn’t a trick question to see if they cheekily include you in their life!

It’s a way of seeing what things interest them, if they’d rather travel or work their way up their career ladder, if they see themselves buying a house and settling down or if they’re the kind of person who doesn’t plan at all.

It’ll show you how committed they are – and what to. 

16. Do you see your family much?

If they’ve already been a bit quiet when it comes to talking about their family, skip this one!

However, if the topic seems like fair game, this question will help you see how important their loved ones are to them.

It will show you what values you have in common and might even bring up some sweet memories for them to share with you!

17. Are you a morning person?

This is a nice easy one to get them talking a bit more about themselves – it’ll show you an honest insight into their lifestyle, and will help you gauge whether it matches up with yours.

If they hate mornings, but you hate staying in bed past 8am and prefer a partner who gets up to work out with you, you’ll know about this incompatibility early on. 

18. Do you like spicy food?

A great segue if you feel like the date could move to a restaurant! They might share some funny stories about trying very spicy food abroad, or talk about how much they do/don’t enjoy cooking.

You can share your stories, suggest a good restaurant nearby, or invite them over for a home-cooked, spicy (or not!) meal sometime.

19. What’s the weirdest fact about you?

Give them a chance to throw something really random into the ring. Fingers crossed it’s a good one!

You can then share one in return, making this a cool way to learn more about each other than generic, pre-set questions ever could.

20. What do you want to get better at?

You’ll learn what they’re interested in – and not just what they think you want to hear.

This is a great question to get them to open up more about some of their insecurities, too, which will help you both bond a bit more.

Maybe they want to become more creative, or better at running. Either way, you’ll find out a lot more about them with this simple first-date question.

Still not sure what to ask on your first date? Chat online to a dating expert from Relationship Hero who can help you figure things out. Simply click here to chat.

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Remember that first dates are just the tip of the iceberg – people might not show their full, true selves straightaway, and that’s okay!

These 20 fun questions for a first date are designed to help you both break down a few barriers and have a good time together. They’re not your typical date-night questions, so should give you a chance to get a genuine response, not one that they’ve planned in advance!

Enjoy getting to know them, having a laugh and seeing where things take you…

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About Author

Lucy is a travel and wellness writer currently based in Gili Air, a tiny Indonesian island. After over a year of traveling, she’s settled in paradise and spends her days wandering around barefoot, practicing yoga and exploring new ways to work on her wellbeing.