Dating

These 36 first date question will make your date a success!

Sometimes, it's hard to come up with something to talk about on a first date. Fight the awkward silence with these 36 fantastic first-date questions and make your date a success!

Dating Expert David Hall October 11, 2022 • 14 minutes read
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First dates can be as fun as they can be daunting. No matter how many first dates you’ve been on, it’s always tricky to come up with something original and interesting to say.

To help you out, we’ve compiled a list of first-date questions that are sure to get the conversation flowing. From there, it’ll be up to you to keep things going and see where the night takes the two of you.

We’ve divided this list into different categories so that you can easily find the type of question you’re looking for.

Good luck on your first date, and have fun!

But before heading into your first date, check out these guides:

Icebreaker questions for first dates

With these icebreaker questions, you can get to know your date in a fun and relaxed way. Break the ice and start your date the right way with these questions.

If you prefer rather flirty questions, check out these 17 flirty questions that will make your date fall in love with you!

1. Tell me about the greatest summer you ever had as a kid.

Childhood is a great and memorable time for many of us. This question will bring back happy memories and allow you to relive them with your date.

What was the best summer you ever had as a kid? Where did you go? What did you do? Tell me all about it!

2. What’s the best piece of advice you’ve ever received?

We all need great advice from time to time. Getting a little help from a friend is never wrong. And who knows? Maybe the advice they got is something you can use in your life too.

So, what’s the best piece of advice you’ve ever received? And did you take it?

3. What was your first kiss like?

A question like this is bound to bring out the romantic side of your date. And who doesn’t love a good story about first kisses?

Tell me all about your first kiss. Where was it? Who was it with? Was it everything you dreamed it would be?

Do you want to land a kiss on your first date? These 7 breathtaking tips will help you!

4. Tell me about your best friend growing up.

Friends can tell you a lot about a person. So, this question can be a great way to get to know your date better.

What was your best friend like when you were growing up? What did you two like to do together? What was the main reason for your friendship? Tell me all about him or her.

5. Do you have any siblings, or were you an only child?

Like friends, siblings can tell you a lot about a person too. This question can help you understand your date better and maybe even give you some insight into their family life.

Do you have any siblings? If so, what are they like? Are you close to them? Do you get along well with your siblings? Or were you an only child growing up? How was that experience for you?

6. Who is/was your favorite teacher, and why?

Teachers have a huge impact on our lives. They can teach us so much more than just the subject they’re supposed to be teaching.

So, who is your favorite teacher, and why? What did they teach you that you’ve never forgotten?

Fun questions to ask for a first date

Let’s face it, first dates can be pretty awkward. But with these fun questions, you can get the conversation flowing and have a great time together. Fun questions are just that, fun!

7. If you could have any superpower, what would it be?

This question is bound to get your date’s imagination flowing. And who knows? Maybe they have a superpower that you would love too.

If you could have any superpower, what would it be? Would you use it for good or for evil?

8. If you could travel anywhere in the world, where would it be?

This is a great question for finding out what kind of traveler your date is. Are they the type who likes to rough it in the wild, or do they prefer the luxury of a 5-star hotel?

Where would be your dream destination if you could travel anywhere in the world?

9. Are you a dog person or a cat person?

Believe it or not, this can tell you so much about a person. Dog persons are generally speaking rather extroverted and social, while cat persons are often more introverted and independent. Of course, this is not always the case, but there are other questions you can ask to get to the bottom of this.

Are you a dog person or a cat person? Why? Or maybe you’re both!

10. Pizza or burgers?

This is a classic question that can tell you a lot about a person’s taste. Do they prefer the classic comfort food of pizza or the all-American burger?

Pizza or burgers? Why?

So, what’s your favorite? Pizza or burgers? Why?

11. Are you a morning person or a night person?

Many people are grumpy in the morning, while others find it hard to stay awake at night. This question can help you understand your date’s natural sleep pattern and maybe even help you plan a better date.

Are you a morning person or a night person? Why?

12. Imagine aliens visited the Earth, and you were selected to represent our planet. Why’s that, and what would you say to our visitors?

This question is just so much fun! It’s bound to get your date’s imagination flowing, and you might even learn something new about them.

If aliens visited the Earth and you were selected to represent our planet, why would they choose you? And what would you say to them?

Important questions for a first date

Some questions are just necessary for a first date. They help you get to know each other better and can sometimes be the difference between a good date and a great date. Also, they can help you find out if this person is the one you’re looking for.

Some of these questions are better asked later in the date, though, because you want to get to know them a bit first and get rid of the awkwardness. You don’t want to scare them away with questions like these!

13. Are you more ’no strings attached’ or long-term relationship oriented?

It’s almost always good to know what your date is looking for. This question can help you find out if they’re looking for the same thing as you.

Are you more ’no strings attached’ or long-term relationship oriented? Why?

14. Can you describe your ideal partner?

This question can give you a good idea of what kind of person your date is looking for. And who knows? Maybe they’re looking for someone just like you.

Can you describe your ideal partner? What are the most important qualities they must have?

15. Do you want or already have kids?

This is an important question for anyone who is looking for a long-term relationship. Knowing whether or not your date wants kids can help you decide if this is something that you can see yourself doing with them.

Do you want or already have kids? Why or why not?

16. Do you like your life the way it is, or are you looking for something different?

This question can help you find out what kind of person your date is. Are they content with their life, or are they always looking for something more? Is there actually room for you, or could you get in the way of their future plans?

Do you like your life the way it is, or are you looking for something different? Why?

17. What are your thoughts on monogamy?

Nowadays, monogamy isn’t always the norm. So, it’s important to know where your date stands on this issue. Do they believe in it, or are they more open to other options?

What are your thoughts on monogamy? Why?

18. What’s the most important thing you’re looking for in a relationship?

Many people may want a partner for the wrong reasons. Is it companionship, love, or something else entirely? This question can help you find out what they’re really looking for.

What’s the most important thing you’re looking for in a relationship? Why?

Lighthearted questions for a first date

After asking questions that can be a bit harder to answer, it’s important to mix in some lighthearted ones to make your date feel comfortable. These questions can also help to keep the conversation going and can be a great way to find common interests.

19. Do you have any nicknames? What are they, and why do you have them?

Probably everybody has at least one nickname. And not everybody likes their nickname! This question can help you get to know your date better and find out what kind of person they are.

Do you have any nicknames? What are they, and why do you have them?

20. If you could be any animal, what would you be?

This question is just so much fun! It’s better than asking what their favorite animal is because it lets their imagination run wild. It can also tell you a lot about what they value in life.

If you could be any animal, what would you be? Why?

21. What’s your favorite joke?

Everybody loves a good laugh. So, this question is sure to get the conversation going and lighten the mood. It’s also a great way to find out if your date has a good sense of humor.

What’s your favorite joke? Why? Do you know any other good jokes?

22. What would you do with a kiosk in your room where you could order anything you want for delivery to your room without even having to speak?

This question is a bit random, but it’s also a lot of fun. It’s the perfect question to ask when the conversation starts to lag and you need something to break the ice.

What would you do with a kiosk in your room where you could order anything you want for delivery to your room without even having to speak? And why?

23. Imagine you won the lottery; what would you do with the money?

With a question like this, you can find out what your date’s priorities are. Do they want to travel the world or buy a house? Do they want to help others or just enjoy their own good fortune?

If you won the lottery, what would you do with the money? Why?

24. Imagine you can do whatever you want for an entire week. What would you do?

This is another great question for finding out what your date’s priorities are. Do they want to spend time with family or friends? Do they want to travel or stay at home? Or would they enjoy finally having time to read that book they’ve been meaning to get to?

If you could do whatever you wanted for an entire week, what would you do? Why?

Deep first date questions

Some questions can be tough to answer, but they can also be a lot of fun. These questions can help you get to know your date on a deeper level and find out what they’re really like. But it’s better to ask them later than sooner.

25. What’s your biggest fear?

Everybody is scared of something if they admit it or not. Let’s see how comfortable your date feels with sharing this info with you.

What’s your biggest fear? Why are you afraid of that?

26. What’s the best and worst decision you’ve ever made?

This question can help you get to know your date better and find out what kind of person they are. It can also tell you a lot about their values and how they make decisions.

What’s the best and worst decision you’ve ever made? Why were they good or bad decisions?

27. What’s something you’re passionate about but few people know about?

This question is a great way to find out what your date is really interested in. It can also help you get to know them on a deeper level and find out what makes them tick.

What’s something you’re passionate about but few people know about? Why is it important to you?

28. What’s your biggest accomplishment?

Some people find it hard to talk about themself. But a question like this can show you what they’re really proud of and what’s important to them.

What’s your biggest accomplishment? Why was it so important to you?

29. What would you do if you only had 24 hours left to live?

A bit morbid, but this question can be really revealing. It can tell you a lot about what’s important to your date and how they want to spend their time.

If you only had 24 hours left to live, what would you do? Why?

30. If you were a kid again for a day but kept your adult knowledge, what would you do?

This is a fun question that can help you bond with your date. It’s also a great way to find out what they’re really like when they let their hair down and have some fun.

If you were a kid again for a day but kept your adult knowledge, what would you do? Why?

Random first date questions

The following questions can be anything. They can be fun, weird, serious, or anything in between. The only rule is that they can’t be boring.

31. What’s the most daring thing you’ve ever done?

Some people are scared of heights, and others are scared of public speaking. This question can help you find out what your date is really afraid of and how they like to face their fears.

What’s the most daring thing you’ve ever done? Why did you do it?

32. What TV show do you think deserves to be canceled?

Everybody has that one TV show that they just can’t stand. This question can help you find out what your date’s taste in television is like and whether or not you share the same taste.

What TV show do you think deserves to be canceled? Why?

33. If you could have any creative job, which one would you pick?

Let’s find out which creative job your date would love to have. This question can also tell you a lot about their passions and what they’re really interested in.

If you could have any creative job, which one would you pick? Why?

34. What would you do if you suddenly had a third arm?

A weird question, indeed. But what would your date do? Would they freak out, or would they embrace it by learning how to use it?

What would you do if you suddenly had a third arm? Why?

35. If you could be anyone else for a day, who would you be?

This is a great question to find out who your date looks up to. It can also tell you a lot about what they wish they could change about themselves.

If you could be anyone else for a day, who would you be? Why?

36. You’re selected for a mission to Mars without any training; there’s no return. What 3 things do you take with you?

An interesting question that can tell you a lot about your date. What would they bring with them? Would they bring practical items, or would they bring items that would make them feel comfortable and at home?

You’re selected for a mission to Mars without any training; what 3 things do you take with you? Why?

There you have it: 36 first-date questions to help you get to know your date better. Remember, the most important thing is to relax and have fun. Don’t worry if you don’t have all the answers to these questions. Just enjoy getting to know your date and let the conversation flow naturally.

Good luck with your first date!

PS: So, your first date was a success; now what? Well, get prepared for the second date with these 25 fantastic second-date questions!


How to win at early stages dating: The ultimate list of books

If you're looking for books about the early stages of dating, you've come to the right place. We've put together a list of some of our favorite books about dating, all of which are perfect for early stages in a relationship.

  1. Dating Sucks, but You Don't: The Modern Guy's Guide to Total Confidence, Romantic Connection, and Finding the Perfect Partner
  2. Seven Secrets of Modern Dating: The He Said, She Said Guide for Getting from Single to Spouse
  3. First Date Mastery: The Complete First Date Psychology Guide For Men
  4. Just Send the Text: An Expert's Guide to Letting Go of the Stress and Anxiety of Modern Dating
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Dating Expert

David Hall

David Hall is a self-taught dating expert who works as a freelance writer to help people improve their love lives. He has always been interested in dating, physical attraction, and …

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