201 Best First Date Questions & Pro Tips to Start Conversations

What makes a perfect first date? Was it her smile on every single one of your jokes? Or was it her hair complimenting her slender neck? Or was he too good with his table manners? 

Let me tell you the answer to that; it’s the answers you got from your first date questions. 

Believe it or not but everyone has a few first date questions on their mind, and the answers they receive, encourage them to think about the next date. But are you absolutely clueless about which questions to ask? Then this post is here to make things simpler for you. 

But what happens after you have asked these questions? How can you make your date an extraordinary experience? Just asking questions isn’t going to save you. After all, it’s a date and not some interview. But these questions can play a very significant part. So how to go about them?

How To Select Your First Date Questions?

  • Are you planning to extract the reaction about something you consider as a major deal-breaker? In this case, you shouldn’t be very pushy about it. Try and figure out what information is necessary for you to know about the person straightway. Make sure you don’t ask for anything too embarrassing to discuss on the first date. 
  • It’s advisable not to ask too much about his/her ethnicity, caste, creed, or religion. If you can already guess that from her or the words, he/she frequently uses during the conversation, then fine otherwise, nobody wants to talk about their religion or beliefs on the first date. You can surely pass a compliment about her accent if you find it more interesting than yours but don’t try to push it any further. 
  • Don’t ask too much detail about their work or professional sphere. It’s not rude to ask what someone does for a living, and of course, you are not in high school anymore, but it is better to avoid the details. For example, if he said that he is a sales executive, then that’s enough information for you on a first date. You will have plenty of occasions later to ask these details, but your objective should be to form a connection right now. Asking about their monthly income is a big NO-NO! Don’t be a price tag! This may not be a huge problem for people dating people of the opposite s*x, but if you are dating people of your same gender, then don’t get into too much with the price of their outfit. A sweet remark on their attire is always appreciated, but you don’t have to know the names of the stores they went to.
  • Try not to choose a place too bizarre! Remember that you are on a date and therefore, you need to choose a suitable place for that. Maybe you really love the zoo, and there is nothing wrong with that. However, that may not be a very good choice for a date. Remember, the first impression may not be the last impression, but it is still quite significant.

Also Read: Why Do Men Pull Away & Lose Interest?

What Are the Questions You Can or Should Ask on Your First Date?

Well, there can be hundreds of questions you can ask on your first date. But you must go by the vibe of the person and also the setting and ambiance of the place. This is why I have separated these questions into a few categories. Like you can go for the funny ones or even some straightforward ones.

The Kind of Funny Ones!

1. What compliment completely blew you away, and who gave that? 

Taking by surprise is the goal here, and you would surely surprise her in a good way!

2. Would you choose between living in squalor for a month with your best friend and living in a huge mansion for a year with your enemy? 

You never know the kind of answer you will get, but the conversation will surely reach a new angle.

3. Do you brag about something about yourself? 

Maybe you will get to know something interesting or unexpected.

4. Do you have any other plans for the rest of the weekend?

Maybe the answer will be kind of obvious, but still, you would have something to talk about.

5. When was the last time you visited a great restaurant? 

Just some small talk, but it can be effective.

6. Do you have any plans after this date? 

Again, a kind of obvious answering question, but these small talks can continue the conversation.

7. Tell me about your biggest adventure.

This can reveal something interesting, and you can talk about that. 

8. Give me a list of your favorite five cities and why?

Plenty of subjects to talk about further. Handy questions. 

9. Do you Google everything?

 Small talk, but you can develop the next few sentences based on the reply.

10. Do you know what the longest word in English is?

 Ice breakers are effective if you suddenly run out of things to say.

11. What is your biggest fear in life? 

Also Read: How to tell love from a crush

 A great question to take the conversation to a different level. 

12. Do you currently have anything in your freezer?

 Again, small talk but interesting ones.

13. If you write an autobiography, then what would be the title? 

 This kind of question will supply material for some more questions.

14. Tell me your favorite pick-up line. 

Conversation starters.

15. Do you go to the movies alone? 

 Conversation starters. One thing can lead to another.

16. What kind of pizza do you love the most? 

It is always nice to ask about the food they love.

17. Tell me the name of your two favorite albums.

Music is always an obvious choice.

18. Do you often go on a walk all by yourself? 

Conversation starters.

19. Have you ever been into a fight?

Interesting points to develop further.

20. Tell me your all-time favorite piece of furniture.

Ice-breakers, and it will lead to other things.

21. Have you done anything charitable lately?

Same kind of question but a different tone.

22. The funniest scenario you can think of in the next ten seconds.

 Classic ones, they will never disappoint you.

23. Do you find any animal really ugly? 

Ice breakers if you suddenly run out of things

24. What was the most recent book you read? 

Classic ones, they will never disappoint you.

25. How do you imagine the world around you in the next 70 years?

Interesting question; supplying enough things to talk further.

26. What is your favorite television show? 

Some classic questions are always welcome.

27. The best thing you learned during college freshman year.

Ice breaker kind of thing. 

28. What’s the worst film you’ve ever seen?

 I mean, everyone wants to know this.

29. Have you ever experienced any kind of meetup group?

 Ice breaker kind of question

30. Can you imagine any sport where players would play while being drunk? 

Another ice breaker kind of question.

31. What would you prefer between fresh flowers and fresh fruits?

These questions can always reveal a lot about the person. 

32. How many times have you bunked a class?

Old stories, everyone loves it.

33. Have you ever thought about starting a band? 

Fantasy kind of question.

34. The best year of your life

Same kind of question but with a different tone.

35. The kind of people who absolutely drive you insane

It can give you interesting insights.

36. The best or absolutely stunning view you’ve ever seen

Everyone would like to know something like this.

37. Do you try new dishes at the restaurant, or do you order the same thing every time you visit the place?

Ice breakers but can give you more to talk about.

38. Suppose you are allowed to choose which part of your body would get kicked by a big horse; which part would you choose?

 Just one of those funny ice-breakers.

39. How did it feel when you cooked something for the first time? 

Old stories but interesting.

40. The worst dating experiences.

Everyone has something to say.

41. What would you choose between coffee and tea on a cold, rainy night?

Always will give you something to talk about.

42. Do you dream of becoming a celebrity? 

 I mean, who doesn’t?

43. How do you see the glass, half-full or half-empty?

To know the perspective that matters.

44. Do you rehearse before picking a call from someone special? 

You never know what you will get to know.

45. Have you ever had music lessons?

Again, some old stories everyone wants to talk about.

46. What do you feel like doing the most when you are all alone?

The tense question will surely give you something interesting.

47. Have you ever had a toxic relationship?

Maybe you will get something you will not, but it is worth a shot.

48. What’s the funniest story from your childhood?

 A must-ask question.

49. Do you like or hate your current boss?

Well, need we say more! The best one to elongate the evening.

50. What kind of cloth or fabric do you love the most? 

General but effective. 

Some Good Questions

1. What is your favorite pass-time activity? 

Everyone wants to know about your hobby.

2. Would you call yourself an indoor or outdoor person?

Interesting answers can be expected.

3. The most fascinating person you’ve ever met?


4. Your all-time favorite song? 

The match of musical taste is very important.

5. The one movie you can watch over and over again?

 For future movie dates.

6. The greatest adventure of your life or you have been on?

Everyone likes to talk about this.

7. Do you have any pets?

Maybe you do, but it will take the conversation forward.

8. Your favorite non-alcoholic drink

Who doesn’t like to talk about favorite drinks!

9. Do you have any kind of obsession? 

Driving the conversation forward.

10. What is your most favorite place to travel to? 

Yes, classic one.

11. Do you have a favorite continental dish? 

Food is always essential.

12. Would you call yourself a morning person or night owl?

 The very important question, trust me.

13. Your all-time favorite restaurant

 It can come in handy in the future.

14. Do you have any siblings?

 General information. 

15. What is your dream job?

Conversation builder

16. Suppose you get a lot of money; what would you do next? 

Same kind of question but more interesting.

17. Your favorite author?

 Everyone loves talking about books.

18. Which show you can binge-watch over and over again?

 For future dates. 

19. The most dominant color in your wardrobe

 Everyone loves talking about dresses.

20. Suppose you have a lot of money, what new hobbies would you like to indulge in?

Well, people like talking about fantasies.

21. If they organize an Olympics for day-to-day activities, which activity would surely get you a medal? 

Funny one and an interesting one too.

22. Your favorite place to go for a vacation

Need we say more!

23. What is your specialty among your friends?

 Reveals a lot about the person.

24. The one artist you never get tired of hearing

 Music and art are classic topics.

25. Some of the accomplishments that made your parents really proud

She will indeed be intrigued to talk about.

26. Do you have any obscure angle in your life? If so, what is that?

Interesting angles can be explored.

27. According to you, tell me some of the things that everyone must try at least once.

Well, you will get to know the perception.

28. The one subject you always struggled with within the school

 Same kind of question, general curiosity

29. The best thing that happened to you this month?

 Everyone loves talking about this.

30. Describe to me your perfect morning.

Another interesting thing. 

31. What kind of sports are you into?

 General curiosity

32. The one thing you are ready for

Again, allowing you to have a better perception.

33. What is your favorite activity to relax?

 General curiosity.

34. What is the most useful app you have on your phone, and why? 

Well, you know, those good-to-know questions. 

35. The animal you think is the cutest of all.

Let’s talk about animals.

36. Who is, according to you, the greatest philosopher? 

Well, it can drive the conversation further.

37. That one shirt which is still very close to you 

Interesting one.

38. How would you describe your kind of people? 

 You never know what kind of answer you will get.

39. What, according to you, is the strangest place to be on this planet?

 You might just get to know something truly unexpected.

40. A silly fear that you have

 We all have, and it can be a great ice breaker.

41. The one city you can visit over and over again. 

You will have something interesting to know. 

42. What is the worst possible household chore, according to you?

Well, everyone can relate to this one, isn’t it?

43. Apart from the one you have, what nickname would you give yourself? 

This can also drive the conversation further.

44. An odd talent you think you have 

Some interesting things can be heard.

45. If you become president for a day, what would be the first thing you would do? 

This can really take the conversation to a different side.

46. The one subject or topic that always kind of intrigues you the most 

 Good to know kind of questions.

47. One country you would never want to visit

 This will give you enough things to talk about more.

48. The one assumption that almost everyone makes about you.

 Well, it can reveal something about your date.

49. Would you like to work in a team or alone?

This can also reveal a lot about the person.

50. The best period of your life and why?

You can make a mental note and elaborate on the topic later.

Some Unique Questions

1. If you had a time machine, which period would you like to visit? 

It is unique, and you never know what you get.

2. Imagine you are in high-school again; what dating advice would you give yourself? 

Unique questions will never disappoint you.

3. Which city would you like to go to if you are given a job? 

It will give you something to talk about.

4. Suppose you have to wear a shirt for one whole year, which one would that be? 

The answer can always surprise you.

5. If you are allowed to write a letter to yourself, what age would you write to? 

Well, you know, it will be interesting, right!

6. Imagine you are having a dinner party and you are allowed to invite anyone. List ten people you would invite.

These ten people can take the conversation further.

7. What would you do if you found a duffle bag full of cash? 

It can surely give you enough material to go on.

8. The one song you want everyone to listen to? 

Music can never fail you.

9. What makes you feel pampered the most? 

Things to make a mental note of.

10. Do you behave differently when you’re with strangers and how do you act?

 Perception can be presented.

11. The one app you think is not at all useful. 

Good to know kind of questions.

12. Tell me two words that describe you most appropriately.

You can make mental notes on these.

13. What is your favorite perfume or favorite scent?

Gifting ideas

14. The five things, according to you, are a big NO-NO when it comes to dating

All the perception you need to make your next date successful.

15. The one song you think was written for you.

It can be a song you can listen to together.

16. Have you ever spoken before a large audience? 

 Reveals the confident side.

17. What is that one thing you think you have done, but most people haven’t? 

Reveals the kind of choices she would have.

18. Do you regret anything that you have done in your life? 

Reveals the kind of mentality he/she has.

19. The one place your family and friends would be very proud to see you. 

Reveals the kind of aspiration she has. 

20. If you are to keep just a book which one would that be? 

 Reveals the kind of ideas she likes the most.

21. Where would you like to walk on a date? 

Plans for next dates.

22. Are you a bathroom singer, and what is your favorite song to sing? 

 Good to know kind of information and ice-breakers.

23. Would you be able to survive a day without using your phone? 

 You can dare him/her later.

24. Do you like trick questions in general? 

 Reveals something more about her mentality.

25. Do you have some profound secrets? And have you shared that with anyone?

 The conversation will indeed have a lift from this.

26. The one thing you would like to change instantly

 Reveals the ideas she has.

27. The one law you think is absolutely ridiculous.

Reveals here perception about society.

28. What would you choose between true love and $50 million?

 A bit of philosophy never killed anyone.

29. The one thing in your life that you wouldn’t give up no matter what

 Reveals the strongest pillar of his/her life.

30. The dream house, according to you, and how would designs it? 

Reveals her ideas.

31. Tell me something about your days during the COVID-19 pandemic?

Reveals her understanding of various situations.

32. What are the differences you think I have in real life compared to my online self?

Well, you can know what she thinks about you.

33. Would you slap your best friend for an insane amount of money?

Reveals something about her loyalty.

34. Would you reconnect with your ex for some noble cause? 

Interesting answers for sure.

35. What would you do if you had five houses around the world?

 Well, nobody can tell you for sure.

36. Would you like a pet robot to do all your chores?

 It can surely get your conversation to an interesting stage.

37. Do you like trying new and unusual dishes?

 Maybe she does, and you will get ideas for the next date.

38. The one thing you would like to change with the world 

The perception would shine again.

39. Would you prefer a huge joint family or a small one?

 Her definition of a happy family.

40. What is your take on marriage?

This can be important if, however, things move forward.

41. The one question you would surely ask the person you would marry

 Maybe we don’t need to explain as to why this is important.

42. Where do you see yourself in the future?

Everyone wants to know this.

43. What is that one thing that you would always carry?

Good to know things and surely an ice-breaker.

44. The one thing you really want to posses

Her aspiration will be reflected.

45. Do you often cry on things?

 Her emotional quotient is something you need to know.

46. How would you describe a person to someone else?

This is how you would know her outlook.

47. The one high-school memory you can never forget.

Everyone loves talking about these.

48. The one thing that makes you super mad

Indicates her patience.

49. Who would you take along with you if you got to go to Venice? 

You know in case you managed to make an impression.

50. What kind of music do you hate the most?

It’s good to know the other side of things as well, isn’t it?

Some Nice Questions to Ask

1. Apart from your day job, what other things are you good at? 

You will know how talented your date is.

2. The one question you don’t ask anyone

Her sense of privacy can be understood.

3. The three most interesting things to talk about according to you. 

Well, this question can supply you with more material to talk about.

4. The one thing you don’t care about at all.

Her/his attitude can be understood.

5. Do you have a retirement plan?

 Who doesn’t want to know about the future?

6. The weirdest person you have ever seen

 Your date’s perception

7. The one thing about you that surprises everyone

 It will be very helpful for you as well.

8. Would you like to become a pirate?

One of those ice-breakers but interesting ones.

9. Suppose humans don’t have to sleep anymore; what would you do with the extra time?

Again, a similar kind of interesting ice-breaker.

10. When you were a kid, were you a naughty child?

This will reveal something unexpected.

11. The most unexpected way you became friends with someone.

 Your date’s mental flexibility.

12. The one sports personality you absolutely adore

Who doesn’t want to talk about sports!

13. The one phase in your life you consider as a turning point

Everyone wants to know about the most crucial point in your life.

14. The one brand you can swear by

It will indicate her preferences.

15. Do you think even small things can bring you a lot of joy?

This will again reveal her perception,

16. The one sport you don’t like to watch at all.

One of those questions refers to preferences.

17. What do you do when you feel bored

Another way of asking about his/her hobby.

18. What would you choose between texting and sending letters?

It can show how romantic she might be.

19. Have you visited any other country? 

Maybe you can get something out of it.

20. The one band you can swear by

Knowing her taste is very important.

21. Do you miss something from the bygone era? 

It can elongate the conversation.

22. What holiday do you like the most and why? 

Her pleasure-seeking activities.

23. The one thing, according to you, that keeps getting worse in this world.

 Her ideology can be reflected here.

22. The best spot to have a picnic according to you. 

 Good to know information, if you plan a picnic.

25. Your most preferred outdoor activity

You got to know this for the future.

26. Do you do sill dance moves?

 Her unapologetic side

27. One thing that makes you feel bored

 You can avoid doing that altogether.

28. The one habit you always wish you had.

Revels her longing for something.

29. Your preferred way to find out someone’s nature.

This can give you some idea about how to behave.

30. Have you tried anything new lately?

Just small talk

31. The one person who taught you a lot of things other than your parents.

Her emotional anchor

32. When do you feel yourself the most?

 Her truest self, and you need to know all that.

33. Do you believe in God?

This can help the conversation.

34. You think your future self will laugh at the one thing you have done.

We all have something similar to this.

35. Do you use social media a lot?

Good to know information.

36. What is your image with your family?

You must know something about this. 

37. What would you choose between the weekend and weekdays?

Well, this will help you plan your next date.

38. The one thing you are always looking forward to happening.

Her aspiration and dreams are reflected.

39. That one guilty pleasure you have.

 We all have one such pleasure.

40. The worst job you ever had.

Can you think of any other better question to start the conversation?

41. If your life was a novel, are there any plot twists?

Well, again, something about the perception.

42. Your best family vacation ever.

You can try that sometime later as well.

43. That all-time super funny story.

 We all need a story to laugh at whenever things get serious.

44. If your life had a slogan, what would that be?

Creativity! Of course

45. Apart from your job, what other profession would you have gone for?

 Maybe her future plans.

46. How can you balance your personal and professional life?

This is very important for your dating life.

47. The happiest moment of your life.

 Can you recreate that?

48. Choose between a fast car and a fast bike.

  Small talk but can give you something to talk about.

49. The one social situation you always try to avoid. 

We all have one such scenario.

50. The friendship you treasure the most.

 Her best friend you need to know about.

51. The one thing that makes you different from most other people out there.

 This can lead to some great conversation.

Let’s Start the Conversation

Having a great conversation with someone who can reciprocate is a real pleasure. But starting one such conversation is pure art. Many people are very much skilled in continuing the conversation. However, starting it off is where we falter. Below I am going to list a few pointers that will help you start a good conversation effectively.

  • Go ahead with a compliment! Yes, this one never fails. I mean, who doesn’t love getting compliments? This is why it is considered a full-proof plan. If your date is a woman, nothing can be better than this. You don’t have to go over the top for this. I mean, it can be a sweet and simple compliment about her eyes or the attire she is wearing. And you are on to it? More than the conversation, it will set the tone about yourself. After all, if you don’t come across as someone nice, then it would help in the rest of the date!
  • Don’t start with something very controversial or emotionally taxing. Maybe on your way to the restaurant, you read a very philosophical quote on Facebook or a moving picture of poverty and despondency, but that’s fine; keep it to yourself for the time being. There is no need for you to start the conversation with that topic. It’s your first date; after all, do you wish to drive her to tears? Or worse, do you wish to bore her with an in-depth discussion on existentialism? If you wish to choose neither, then please start with something light like, “Hey, this place has nice music, isn’t it? 
  • Try to be conversational and allow the person to reciprocate to you. I mean, you don’t want to lecture your date right even if you are a professor in your day job, isn’t it? So, make sure you add enough chances for her to reply and reciprocate to you. One can do that by adding some spaces to the conversation. This is how the conversation can go forward. 
  • Start with small talk and try to get into a story. We all love stories, narratives, and things that are good to hear. Everyone would like to hear stories, and that’s exactly the kind of thing people would like to hear on a date. Choose something interesting and slowly build your way into it.
  • Use the bookmarking technique. This is something that anyone can use with a bit of practice and instinct. The results can simply blow your mind away, and you wish why you haven’t used it sooner. All you need to do is carefully observe the conversation and make mental notes about the topics you think can take the conversation deeper. This technique can supply you with an endless number of topics to continue the discussion without sounding boring. Making mental notes this way can also prove you to be observant.

What Remains?

So, there you have it. 201 first date questions and 5 amazing pro tips to strike a great conversation. Well, now you are absolutely ready to go on your first date. Remember to reflect well on all the responses you get from the questions. This will help your dating life.

Should you have any further queries on this topic, please feel free to mention them in the comments section.

Refer to our a few articles.

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Healthy relationship

20 signs She is Losing Interest in you

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