390+ Questions To Ask On A First Date

by April Maccario

Meeting someone new can be both exhilarating and scary for so many reasons. If it happens to be a guy, obviously in this case it is, then nervousness takes the anticipation for the first date to a whole new level. 

For one thing, it’s a long process knowing someone and you aren’t sure if becoming friends will lead to something more or if it won’t work out at all. 

To get over the awkwardness and uncertainties of first dates, you need to prepare in your mind questions that you can ask so you can get to know this guy better. In this article, I have compiled 390+ questions for a first date to help you get to know him better.

390+ Questions For The First Date

questions for the first date
  1. Did you find the way here well?
  2. Can you recommend anything from the menu? 
  3. Do you have a favorite drink/favorite dish here?
  4. Isn't the weather great today?
  5. What do you enjoy about this place here?
  6. Don't you find it unusual at first to see yourself real? 
  7. Are you as excited as I am? 
  8. What was the most embarrassing YouTube video you've seen lately?
  9. Have you ever experienced funny things in high spirits in your youth?
  10. What's the funniest first or last name you've ever heard?
  11. Which skill do you prefer: to be able to fly or to be invisible?
  12. Beer or wine, what tastes better?
  13. Late risers or early risers?
  14. What’s your favorite: Netflix or Amazon Prime?
  15. What do you prefer for a present: roses or cactus?
  16. Vacation in a luxury hotel or camping with tents?
  17. What’s something you take very seriously?
  18. How do you spend the perfect Sunday?
  19. Which is cooler, the Simpsons or Family Guy?
  20. Motorbike or bike?
  21. Apple or Samsung - who has better cell phones?
  22. Cut spaghetti into small pieces or wrap around the fork?
  23. Prefer city breaks or a trip to the countryside?
  24. What kind of art do you like?
  25. Do you prefer to go to IKEA or do you prefer individual furnishings?
  26. What can you really get excited about?
  27. Did you ever want something that you didn't want anymore?
  28. Is the glass half empty or half full for you?
  29. Read a book or watch a film?
  30. What’s something you’re likely to spend big money on?
  31. Where do you prefer to go shopping, perfumery, or hardware store?
  32. Ketchup or mayo with french fries?
  33. Shaved smooth or three-day beard?
  34. Showering or bathing?
  35. When are you fitter, during the day or at night?
  36. Chrome or Firefox, which browser do you prefer to use?
  37. Horror movie or love movie?
  38. Be blind or deaf?
  39. Black or pink, which color do you prefer on clothing?
  40. What’s the best; McDonald's or KFC?
  41. Do you have a piece of jewelry that has a special meaning for you?
  42. What was your last really good concert/festival?
  43. Which zodiac sign are you and do its properties apply to you?
  44. Do you have an Instagram account that you post regularly on?
  45. What series are you currently watching?
  46. Do you have pets?
  47. What kind of sports do you do?
  48. Do you play an instrument?
  49. What is your favorite type of ice cream?
  50. Where were you on last vacation?
where were you on last vacation?
  1. What is your typical clothing style in everyday life?
  2. Do you enjoy going to the theater? What was the last piece you saw?
  3. Which regional cuisine do you prefer?
  4. Is there a game in which you are particularly good?
  5. Do you have a favorite color?
  6. Have you ever ridden a horse?
  7. Where should the next vacation go and why?
  8. Which actor do you enjoy the most?
  9. What do you particularly enjoy about your job?
  10. Is there a fashion word that you use a lot now?
  11. What’s your favorite animal?
  12. Do you have any fancy hobbies?
  13. Are you a volunteer?
  14. Which sports do you enjoy watching?
  15. What do you dress up for at Carnival / Halloween?
  16. When was the last time you were in the museum?
  17. Do you have a colleague with whom you get on particularly well?
  18. Can you knit or sew?
  19. What do you like to eat for breakfast?
  20. Would you like to work in a chocolate factory?
  21. Can you wiggle your ears?
  22. Which of the gummy bear gang would you most likely marry?
  23. Do you think there is a coffee break at noon in the tea factory?
  24. Have you ever done something illegal?
  25. Can you touch the tip of your nose with your tongue?
  26. What was the worst fashion sin in your youth?
  27. What’s something you want to get to know more about?
  28. Did you play funny pranks as a kid?
  29. Do you know a good joke that really makes you laugh? Tell me!
  30. Who spends more money shopping, men or women?
  31. Do you have a strange habit?
  32. How did you find out that Santa Claus doesn't exist?
  33. Are you a morning person?
  34. Which year would you like to travel to if you had a time machine?
  35. Which film made you laugh the last time?
  36. What was your first computer/cell phone? (Joking together about outdated technology from back then!)
  37. What do butterflies actually have in their stomach when they're in love?
  38. Can you sing a song (Then ask them to sing!)
  39. Have you ever had an accident that makes you laugh today?
  40. Imagine marrying a celebrity. Who will you choose and why?
  41. Can frogs cry?
  42. What was your relationship with your parents like, were you more daddy or more mom?
  43. What thing do you absolutely want to have that you can't buy with money?
  44. What was the best decision of your life?
  45. Have you ever lied to a big deal - and if so, why?
  46. Which decision in your life do you regret the most?
  47. Is there anything you really want to do again?
  48. Do you believe in magic?
  49. What are you doing to motivate yourself for one thing?
  50. What should your life resemble when you are old?
what should your life resemble when you are old?
  1. If you had to emigrate, which country will you choose?
  2. What will you do if you had only one day left to live?
  3. What fairy tales and stories caught your eye as a child?
  4. Are there qualities in you that you don't like yourself?
  5. What’s the meaning of the motif of your tattoo? (if he is tattooed)
  6. Which country do you really want to travel to again and why?
  7. If you could go back in time and meet your former self, what will you tell him?
  8. What was the last film you cried on?
  9. What was the last gift you were really happy about and why?
  10. Is there a specific motto/quote that you use to go through life?
  11. What’s the relationship like with your siblings?
  12. Which of your relatives do you best cope with?
  13. What’s your biggest weakness?
  14. Is there a specific animal whose characteristics you admire?
  15. Which person is the greatest role model for you?
  16. Imagine your house is on fire and you could only save three items from it. What will you choose?
  17. How did you spend Christmas as a child?
  18. Do you believe in life after death? Why not)?
  19. Have you ever had a supernatural experience?
  20. What will extraterrestrials think about us humans if they watched us?
  21. Do you believe in divination/telepathy/ghosts?
  22. If God created the world, who actually created God?
  23. Can there be a highly developed artificial intelligence that has a soul like a human being?
  24. Does it actually make sense to always be happy, or do you also need bad experiences in life to be able to better appreciate happiness?
  25. Is man really an "intelligent" species when he destroys his own planet?
  26. Where does evil in the world come from?
  27. Do you believe in coincidence or fate?
  28. What’s behind the universe?
  29. Is there selfless action at all (altruism) or do you ultimately do everything just to satisfy your own ego?
  30. Can you be in love with two people at the same time?
  31. How does a blind man imagine colors when he is blind from birth and could never see?
  32. Will there ever be a medicine that will give us eternal life? And will that be desirable at all?
  33. What is this light at the end of the tunnel that people with near-death experience describe?
  34. Are dreams really just foams, as the saying goes, or is there a spark of truth in them?
  35. Why does modern art look so damn ugly?
  36. What do you think, who were you in a previous life?
  37. Doesn't everyone need social relationships or can you really be happy as a hermit?
  38. What will our world resemble if we have perfect artificial intelligence and all work is only done by robots?
  39. Do you know that: You think of a good friend and she calls you a short time later ... Is that a coincidence or is there a spiritual connection?
  40. If God is almighty, can he create a house that is so solid that he cannot destroy it himself?
  41. Are children happier than adults - and shouldn't we all be children again?
  42. Do you think there is still a parallel universe somewhere with doubles of us who are also sitting at the meeting?
  43. Have you ever really fallen in love?
  44. Do you want to get married sometime or is it enough for you to live so happily in a partnership?
  45. Do you believe in love at first sight?
  46. Do you have a best friend?
  47. Have you ever been disappointed in a relationship?
  48. Have you ever reacted really jealous?
  49. Do want to have children later?
  50. How can you really get upset in a relationship?
how can you really get upset in a relationship?
  1. How do you imagine the perfect dream wedding?
  2. Do you think you can still have contact with your ex-partner after the separation?
  3. Would you start a relationship with the ex again if he really changed for the better?
  4. Who are your top 5 friends who will take you on an adventure vacation?
  5. Do you think that friendship between men and women is possible?
  6. Have you ever been in love unhappily?
  7. What do you want to do differently in a partnership than your parents?
  8. Do you believe in the saying: "Old love doesn't rust?"
  9. What are the three most important things a relationship must have?
  10. What do you pay the most attention to when looking for a partner?
  11. What is more important in life, relationship, or friendship?
  12. Do you believe in “love for life”?
  13. Hey, either-or question: Have to do without your favorite food for a lifetime or not have sex for 10 years?
  14. Isn't it inhumane to have your pets neutered? 
  15. Did you read "Fifty Shades of Gray"?
  16. Can you really live happily as a monk or nun, or isn't sexuality a basic human need that needs to be met?
  17. Which celebrity would you sleep with?
  18. Where do you look first when you see an attractive man?
  19. Why do you see so many party photos where girls kiss?
  20. Who cheats more often, men or women?
  21. Have you ever watched porn?
  22. What things do women always have in their handbags? 
  23. What do you think about people who don't want to have sex before marriage? Can you be so happy?
  24. Have you ever had an embarrassing experience in the swimming pool?
  25. Are women really into six-packs?
  26. Would you accept an "immoral offer" for ten million euros?
  27. If you do it skillfully, the woman will have to think about sex - maybe even with you!
  28. What’s your favorite thing to do at night?
  29. What is your favorite song and what does it mean to you?
  30. What three words would you use to describe yourself?
  31. What was the most embarrassing moment in your life?
  32. What else is at the top of your bucket list?
  33. Are you particularly proud of something in yourself?
  34. What was your nicest birthday present?
  35. Are you spiritually touched?
  36. Do you remember your first kiss?
  37. Which of your friends shaped you the most?
  38. Do you follow your head or your feeling?
  39. How was your driving test?
  40. What do you do passionately?
  41. What would surprise me about you?
  42. What would we do now if we were on vacation together?
  43. Are there people who don't like you and why?
  44. What's the funniest joke you know?
  45. Which film makes you laugh / which makes you cry?
  46. Have you ever been to a poetry slam?
  47. Do you have a favorite place you'd take me to?
  48. Do you believe in love at first sight?
  49. What is the relationship with your parents like?
  50. Do you believe in God and how do you imagine him?
Are you superstitious or do you believe in ghosts, conspiracy theories, extraterrestrials?
  1. Are you superstitious or do you believe in ghosts, conspiracy theories, extraterrestrials?
  2. Do you think sex helps against headaches?
  3. Do you think a long-distance relationship can work?
  4. Do you think there is an age when you are no longer allowed to be a virgin?
  5. Do you think it's important to learn something artistic?
  6. Have you ever looked at one of your teachers?
  7. Do you have a favorite movie?
  8. Do you have unusual hobbies?
  9. Do you have bad habits?
  10. Have you ever used drugs?
  11. What was the funniest thing you've ever seen in school?
  12. Do you have pet names? If so, how did you get these?
  13. Have you tried online dating before?
  14. What was the biggest pot you stepped on?
  15. How many kids do you want?
  16. What do you think of adoption?
  17. What do you want to do next weekend?
  18. Did you read an interesting book recently?
  19. Have you ever had a conflict with the police?
  20. Have you ever received a marriage proposal?
  21. What experience has changed your life the most?
  22. Have you ever had a catfight? Who won??
  23. Who was the first time you fell in love with?
  24. What do you do when you get bored sometimes?
  25. What would you do if you weren't financially dependent?
  26. What was the craziest thing you've ever seen?
  27. What is your greatest fantasy?
  28. Do you believe in kinship?
  29. Who taught you how to ride a bike?
  30. Do you know contact dance?
  31. Do you know any dialects? ("Show them to me ... dare!")
  32. Can you cook well?
  33. What does your dream house look like?
  34. What are romantic places for you?
  35. What is your favorite place in this city?
  36. Do you prefer reading books or watching films? Which do you prefer?
  37. Do you have pets or did you have any? Which pet do you want most?
  38. Which decision you had to make most affected your life?
  39. What do you enjoy about me?
  40. Which characteristics of you do you often receive compliments for?
  41. Do you have a morning routine?
  42. Put your iTunes on shuffle and name the first six songs.
  43. Prefer beach vacation or city trips?
  44. What are your weaknesses? (Personal question)
  45. Would you prefer to be poor and good looking or rich and ugly? 
  46. Have you ever been to dance school? Can you dance?
  47. Why did your last relationship break up?
  48. What inspires you about the city you live in?
  49. What always makes you laugh?
  50. Are you more a robber's daughter or a princess? And why?
are you more a robber's daughter or a princess? and why?
  1. What do you think about this saying: Where there was fire, ashes remain.
  2. What's the funniest porn title you know? (Porn ping pong)
  3. What do you like about relationships?
  4. What was your biggest sporting success?
  5. Assuming the two of us have a private jet, where should the trip go?
  6. How do you want to be remembered after your death?
  7. What do you think is the key to a good upbringing?
  8. What should your life resemble in 10 years?
  9. If we are grandparents, what would be our favorite activity?
  10. What do you enjoy in your fridge?
  11. What is the best thing about family life?
  12. What is your relationship with your grandparents?
  13. Which type of ice cream is your favorite?
  14. What is your star sign?
  15. What is your dream job?
  16. Do you have roots in foreign countries?
  17. What is your earliest memory?
  18. Do you prefer going to the cinema or eating out on a first date?
  19. What was your hottest festival or concert?
  20. Have you ever had an open relationship?
  21. What is the best memory of your family?
  22. What do you prefer? An exotic meal in a 5-star hotel or a delicious chocolate cake from the bakery?
  23. What is more important to you? A great relationship or a lot of money?
  24. What do you prefer to do, save money or spend it?
  25. What is a good partnership?
  26. Which song best describes your life?
  27. Have you ever made sushi yourself?
  28. Would you prefer to be more controlled or uncontrolled sometimes?
  29. What was your most spontaneous action?
  30. What are the most important things in your life?
  31. What are good leisure activities that the family can do together?
  32. Have you ever skydived?
  33. Have you ever swam in the sea at night?
  34. What turns you on most? 
  35. What turns you off the most?
  36. What was the last thing you cooked?
  37. What was the bravest thing you did in your life?
  38. What was the most romantic experience you have ever had?
  39. What was the wildest thing you did?
  40. What was your most creative disguise for Halloween or carnival?
  41. What has touched you most emotionally recently?
  42. What was the funniest moment this year?
  43. What was your craziest encounter?
  44. What would you prefer, true love, or winning the lottery?
  45. What do you want to achieve in a year at work or at school?
  46. What would you do without electricity for three days?
  47. What do you do to make a good impression on a first date?
  48. Which other language would you want to speak and why this one? 
  49. Have you ever met a celebrity? 
  50. What personal question do you want to ask me?
what personal question do you want to ask me?
  1. What bad habit would you prefer to give up?
  2. What are your good habits?
  3. What is your favorite quote?
  4. Have you ever had a completely different look?
  5. What kind of music do you enjoy the most?
  6. What plans or goals do you have for the future in the financial area?
  7. If we were in a band, which instrument would you play?
  8. Who is your role model? (good question for pause)
  9. Would you rather go camping or to the hotel?
  10. Which fruit shake do you want to drink?
  11. Which day of the week do you enjoy most?
  12. What was the best advice you have ever been given?
  13. Which is your favorite book and / or who is your favorite author?
  14. Which funny cartoon is your favorite?
  15. If your house were on fire and you could only save one item, which one would that be?
  16. Could you choose between your job and your relationship?
  17. If your life was a book, what title would you give it?
  18. If for some reason your parents didn't like me, would that be a reason for you to break up with me?
  19. If your best friends described you, what two traits would each name?
  20. How long have you known your best friends?
  21. What do you want to change in your life?
  22. If you had your own country, what laws would you make?
  23. Can you massage well? 
  24. If you met a genie, what would you ask for?
  25. Do you have tattoos or what would you be most likely to get stung?
  26. If you could invite three people from history to dinner, who would they be?
  27. If you had a sign around your neck, what would it say?
  28. If you rewind a day in the past, which one would it be and why?
  29. How do you relax after work?
  30. What do you want to change in your body?
  31. What do you want to change in the world?
  32. If you could have superpowers, what would they be?
  33. When the world goes down today, how would you spend the rest of your time?
  34. Who is your childhood hero
  35. Who is your favorite star
  36. Who is your favorite cartoon character?
  37. Who was the most influential person in your life for you?
  38. Have you ever loved a friend?
  39. What was your funniest nightlife experience?
  40. How do you vent your anger?
  41. Have you ever lost your cell phone? And how did it come about?
  42. How often do you speak to your parents?
  43. What is your favorite way to spend a Saturday?
  44. What is your favorite way to spend New Year's Eve?
  45. How many children do you want to have later?
  46. How long did your longest relationship last?
  47. What were you afraid of in your childhood?
  48. Have you ever heard a rumor about you?
  49. Have you ever come into contact with a crazy or particularly funny sex fetish? (Intimate and funny question at the same time)
  50. Would you break the law to save a family member?
can you imagine living abroad one day?
  1. Can you imagine living abroad one day?
  2. Would you put up with the job of not being able to see your family anymore?
  3. What was your best experience with the starry sky?
  4. Are you an empathic person?
  5. Do you have high demands on yourself or your environment?
  6. Are you satisfied or dissatisfied more often?
  7. What situations do you try to avoid in your life?
  8. What is your next vacation destination?
  9. Do you enjoy traveling by train and enjoy the quiet hours with a coffee or do you find it annoying?
  10. Do you want pets later or are you afraid of the many hairs?
  11. Summer or winter?
  12. Do you prefer to eat less or feast and do sports instead?
  13. What do you wear to bed?
  14. What is your favorite clothing brand?
  15. Why was the last time you cried?
  16. Which colors describe your personality and why?
  17. If you were an animal, which one would you be?
  18. How often do you shower and how long do you need?
  19. Which magazines and newspapers do you prefer to read?
  20. What are your favorite books?
  21. Which film do you enjoy the most at the moment?
  22. Which band have you particularly enjoyed listening to in the past few days?
  23. Which cocktail do you order most frequently?
  24. What is your favorite meal?
  25. Which actor do you particularly like?
  26. You can find a full wallet on the street. Do you give it away or do you keep it?
  27. Go partying or a romantic dinner?
  28. What was the worst place in your life you have ever visited?
  29. Backpacking vacation through Australia or a four-star hotel in Switzerland?
  30. What is your philosophy of life?
  31. In which situation were you happy that you lied?
  32. What do you think of when you think of your ex-friends?
  33. Are you an introvert or an extrovert?
  34. What do you mean by "romantic"?
  35. Do you resemble your parents or siblings?
  36. Do you prefer to live in the country or in the middle of a big city?
  37. At what age did you lose your virginity?
  38. Which part of the body do you enjoy most about the opposite sex?
  39. Sexually speaking, what was the wildest thing you've ever done?
  40. Do you think money makes you happy?
  41. The world will be better if ...?
  42. Do you resemble yourself as a child?
  43. What do you do on your weekends?
  44. Do you judge a book by its cover?
  45. What makes you unique?
  46. Dark chocolate or milk chocolate?
  47. Savory or sweet?
  48. Do you know any good jokes?

FAQs

What are good date questions?

There are so many first date questions that you can ask on the first date. They cover both introductory and deep areas that give you an understanding of your date and if he is someone you can go out with again. Asking “what’s your favorite genre of music? What's your dream job or what’s your favorite meal sounds basic, but they’ll do.

What to talk about on first dates?

A first date can start on an awkward note, so you should prepare first date questions or conversation openers that will diffuse the tension. Build on the little information you already know about him before the first date. This can help create an air of familiarity.

What are good questions to ask a guy on a date?

Some good first date questions to ask a guy on a first date include: 

What’s the best thing to have happened to you recently?
What is your perfect morning?
How did you deal with a difficult situation you were in recently? 

What should you not ask on a first date?

There are some first date questions you shouldn’t ask on a first date, not because they are bad but because they might look over sensitive or unnecessarily intrusive towards someone you’re meeting for the first time. 

Such questions on the first date include:

How many sex partners have you had?
How much do you get paid?
Do you own a house or car?
Do you think this might lead to a serious relationship?
Can I meet your sexy friend?

What are interesting questions to ask?

There are interesting conversation starters (or small talk) that you can introduce in the form of first date questions. If you want to know what he likes to eat, ask ‘what’s his favorite restaurant’ If you want to know how many siblings he has, ask him, ‘what was growing up with siblings like’ If you wish to know his hobbies, ask him, ‘what do you do during your free time?’.

To End Things Off,

I enjoyed putting these first date questions together for you, the next time you set up a date, be sure to try asking your date some of these questions. Let me know if these first date questions were helpful and don’t forget to share this with someone who needs to see the article. 

April Maccario
I'm a huge nerd when it comes to understanding how relationships between men and women work, and what drives a certain behavior. I spend much of my time getting into the nitty-gritty and try to share my findings on this site with the hope of making life a little easier for women that are struggling in their relationships or love life.

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