The 131 Least Boring Questions Ever to Ask Your Date

Would you rather have the gift of invisibility or teleportation?

If you could sleep with any celebrity, who would it be?

What is your fondest memory?

What do you hate the most about meeting someone on a first date?

What physical or personality trait of mine do you find the most attractive?

Bang bang!

With these 5 fun questions, you will get to know your date better from the start.

Fancy more fun questions? Read this article and your next date will be a blast. Or if you already have a relationship, you will learn something new about your partner.

In this article you will gain access to:

  • 131 questions to ask your date (funny, interesting, deep, over tinder)
  • The 6 questions that will send you straight to the friend zone
  • The seductive question that Louis and I asked, which resulted in our appearance in De Telegraaf
  • Arthur Aaron’s questionnaire that will make her fall in love with you (tested!)
  • A method to turn every boring question into a fun question (test yourself!)
  • The Proust questionnaire to get to know every side of her personality
  • 2 techniques to liven up the conversation when she gives mundane answers
  • Questions to keep the conversation flowing, during a date or over text
  • A site that gives you a fun, free question every week

By the way, have you seen my free Transformation Kit?

You'll get my best stuff absolutely free: 12 Opening lines that actually work, my 5 best texting tips (including copy-paste lines for Tinder), and the Friendzone Houdini. Download the Transformation Kit here.

6 questions that will send you to the friend zone

Coming in a minute, 131 interesting questions to ask your date.

But first, let’s take a look at the questions you should NOT ask.

Unless, at the end of the date, you want to hear that she had a “nice time,” only to never hear from her again. Otherwise, here are the questions you should avoid:

  • What do you study?
  • What kind of work do you do?
  • What are your hobbies?

These are the kinds of questions you ask because you want to say something, but you don’t know what.

Do you know who asks her these types of questions?

Her boring uncle that she sees once a year at Christmas.

  • Coffee or tea?
  • Dogs or cats?
  • Red or white wine?

These are a little more interesting than “what kind of work do you do?” but come on, bro – you can do better than this.

Now let’s take a look at some questions that she does NOT hear every day.

Questions that are a little wilder, a little more personal.

Research has shown that asking more personal questions on a date results in a closer relationship between two people.

What kind of questions, you say? Keep reading to find out.

25 Interesting questions to ask your crush

Here, we’ll begin with 25 questions about absolutely anything.

See if there’s something that grabs your attention from this list.

Later on, I will share something very powerful with you.

  1. What is the last song you listened to?
  2. What is the most ridiculous rule that you simply MUST follow?
  3. If you could change one thing about the world that is not only to your advantage, what would it be?
  4. What are you afraid of?
  5. In what ways are you more masculine and in what ways are you more feminine?
  6. What would your perfect room look like, where you could spend all your free time?
  7. What is the most annoying question you get asked on a date?
  8. What brings your family members together?
  9. Would you like to have other people in your family as your parents?
  10. Would you rather receive €1 million all at once, or wait 30 days to receive 1 cent that is doubled every day?
  11. What word best suits you?
  12. How do you spend your time when you are not doing XYZ?
  13. If you could describe your life in three words, what would those words be?
  14. Have you ever made a list of things you want to do before you die? What is the first point on that list?
  15. Would you prefer to sit on someone’s lap or have someone sit on your lap?

  1. What would you do if you were locked in IKEA for an entire night?
  2. What is something that you would like to do but you just haven’t found the nerve?
  3. What are you most uncertain about?
  4. What is a dream that you can vividly remember?
  5. What does your ideal Sunday look like?
  6. North pole or South pole?
  7. What have you never done before, but would really like to do?
  8. What is your earliest memory?
  9. If you were a character in a book, how would the writer describe you?
  10. What is your view on social media?

If you have a first date planned with a girl soon, I got good news:

I wrote an article specifically on questions to ask on a first date. Check it out here:

>> 47 Powerful Open-Ended Questions to Ask a Girl on a First Date

36 Fun questions to ask your girl by Arthur Aron to make her fall in love with you

This sounds unrealistic, I know. But truly, this questionnaire can make someone fall in love with you. And this is scientifically proven.

The New York Times reported on it, the University of California Berkley wrote about it, and many others have talked about it.

And just like that, the questionnaire has become world-famous.

Arthur Aron came up with an experiment: You and your date sit facing each other and then ask each other 36 questions.

To answer these questions, you have to be honest and vulnerable. So, it quickly becomes very intimate. At the end, you and your date will look each other in the eye for 4 minutes without saying a word.

Many lasting relationships have emerged through this method.

I will now share the questionnaire with you, divided into three sets of 12 engaging questions. Each section is slightly more intimate than the last.

Set I

1. Given the choice of anyone in the world, whom would you want as a dinner guest?

2. Would you like to be famous? In what way?

3. Before making a telephone call, do you ever rehearse what you are going to say? Why?

4. What would constitute a “perfect” day for you?

5. When did you last sing to yourself? To someone else?

6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

7. Do you have a secret hunch about how you will die?

8. Name three things you and your partner appear to have in common.

9. For what in your life do you feel most grateful?

10. If you could change anything about the way you were raised, what would it be?

11. Take four minutes and tell your partner your life story in as much detail as possible.

12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

Set II

13. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

15. What is the greatest accomplishment of your life?

16. What do you value most in a friendship?

17. What is your most treasured memory?

18. What is your most terrible memory?

19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

20. What does friendship mean to you?

21. What roles do love and affection play in your life?

22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

24. How do you feel about your relationship with your mother?


25. Make three true “we” statements each. For instance, “We are both in this room feeling … “

26. Complete this sentence: “I wish I had someone with whom I could share … “

27. If you were going to become a close friend with your partner, please share what would be important for him or her to know.

28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

29. Share with your partner an embarrassing moment in your life.

30. When did you last cry in front of another person? By yourself?

31. Tell your partner something that you like about them already.

32. What, if anything, is too serious to be joked about?

33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

35. Of all the people in your family, whose death would you find most disturbing? Why?

36. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

A warning:

In some studies, no less than 50% of the participants fell in love. So be careful with this powerful tool.

After the questionnaire, look into each other’s eyes for 4 minutes without talking, lover boy 😉

Of course, your date does not always have the time or dedication to do this entire test.

Then just continue by asking another question:

20 Good questions to make your date or partner smile

Do you need some fun questions that are a bit lighter?

In this fun questionnaire, you will certainly find a few questions that make you laugh.

  1. What do you dislike the most about dating?
  2. What things really make you smile?
  3. When your dog farts … Do you leave the room or do you pull yourself together?
  4. What was the worst kiss you have ever had?
  5. What special habits do you have?
  6. What makes you really annoyed?
  7. Have you ever peed in a swimming pool?
  8. Do you snore, steal the blankets, or do you roll a lot in your sleep?
  9. If we were at a party in a group, and I make a super bad joke that nobody laughs about … What would you do?
  10. Do you sleep with a stuffed animal / teddy bear or something else?
  11. Have you ever looked in the mirror and winked at yourself?
  12. How are you if you don’t get what you want?
  13. If you could jump into a swimming pool full of something … What would that be?
  14. What is the weirdest nickname you’ve ever had?
  15. What is your favorite joke?
  16. Do you think that fish are sometimes thirsty?
  17. What is the first thing you would do if you were the opposite sex for a day?
  18. What would you do if you won the lottery?
  19. What is the nastiest food you have ever eaten?
  20. What has been the funniest moment in your life?

Now, these questions are great if the girl in front of you is talkative.

What about if you have a date with a shy girl? In that case, you’ll also need some tips on how to keep the conversation flowing.

Read this article:

>> What Should I Say to a Girl – 17 Best ‘Tricks’ to Spark Awesome Conversations

The Proust questionnaire: 34 not always nice questions to ask

The Proust questionnaire is a fun questionnaire to get to know someone’s personality.

The funny thing is that Proust actually did not come up with this questionnaire.

Yet this questionnaire is called that because it became known for the answers Proust gave. Hence the name.

Antoinette, a girlfriend of Proust, had him answer these questions in her confession book.


Some of these questions are not nice questions. They are not all suitable for every date.

  1. What do you think falls under the lowest point of sadness?
  2. Where would you prefer to live?
  3. What is perfect happiness according to you?
  4. What is your idea of being ​​naturally happy?
  5. Which mistakes would you admit the most?
  6. Who are your favorite fiction heroes?
  7. Who are your favorite history characters?
  8. Who are your favorite real-life heroes?
  9. Your favorite painter?
  10. Your favorite musician?
  11. What quality do you most admire in a man?
  12. What quality do you most admire in a woman?
  13. What is your favorite activity?
  14. Who would you like to be?
  15. What is your most pronounced characteristic?
  16. What do you value most in friendship?
  17. What is your biggest defect or disadvantage?
  18. What would, in your mind, be the biggest setback?
  19. What would you like to be?
  20. What is your favorite color?
  21. What is your favorite flower?
  22. What is your favorite bird?
  23. What are the moments when you lie?
  24. What do you like least about your appearance?
  25. Who are your favorite writers?
  26. Who are your favorite real-life heroes?
  27. What are your favorite names?
  28. What do you dislike most?
  29. Which historical figures do you dislike most?
  30. Which military historical event do you admire most?
  31. Which natural characteristic would you prefer to possess?
  32. How would you prefer to die?
  33. What is the current state of your thoughts?
  34. What is your motto?

The #1 way to open her legs soul with good questions

There will be times when you cannot ask all these pre-prepared questions.

Moments when there is no time for crazy questions.

Moments when you have to formulate a question that will address your current conversation.

If your date shares something personal with you, obviously you will not respond with:

“Would you rather sit on someone’s lap or have someone sit on your lap?”

You are probably smiling now, but some men become such robots, that they would do it.


… when you talk to her, remember this:

Ask as few closed questions as possible.

Pro tip:

Ask as many open questions as possible.

It‘s quite logical.

You shoot yourself in the foot with your closed questions.

“Do you like to eat spaghetti?”

She can’t really respond that much. (“Yes or no”)

A closed question closes the conversation.

Do you want to make her bloom?

Then you ask open questions.

Quick exercise:

Make a nice question to ask her. What would be a good open question about food?

Something that gives her more room to answer than “Do you like to eat spaghetti?”.

Do this now. Think of a question or two or three. I also participate and write my answer below. Now I don’t want you to immediately look at my solution. So I leave some space between this mission and my answer.




The first two ideas I came up with were these:

  • “Suppose it is your birthday and you may choose what you eat for breakfast, lunch, and dinner. Which menu do you put together? “
  • “You have 10 euros for your dinner here in [your city here] What do you buy?”

Two nice questions to find out what she likes to eat.

  • Option 1 does not give it a limit in terms of money or time.
  • Option 2 does set limits in terms of money and time.

Besides, it is also useful to say things and make jokes. This way you add something to the conversation, without asking the other person for input.

That’s why I have a download with 12 example sentences here. You can get it easily and for free. After you will also receive daily motivation for flirting with women, tips, and cool videos. Get it here!

Nice questions to ask your date – 2 solutions when she responds boringly

Before you yell:

“Hey Louis, that second question is also a closed question man!”


Technically it is a closed question.

She can simply answer with “spaghetti”.

But chances are high she won’t do this. She will certainly think more and be stimulated to answer more than if you ask if she likes to eat spaghetti.

Pro tip:

If she were to answer your question dry. Then add the magic word “why?”.

“You have 10 euros for your dinner here in [your city here] What do you buy?”



“I actually want sushi but for 10 euros you have way too less and then I am still hungry so I thought about pancakes but I really can’t because I didn’t eat the healthiest this afternoon but yes I really feel like having something delicious and, moreover, I don’t want to ruin this date by eating lettuce so I choose the happy medium and that is spaghetti of course.”

So. Problem solved.

By the way, do you catch yourself asking a closed question here and there?

Don’t panic, sweetie.

That’s totally normal, it isn’t even bad either.

As long as you alternate them with nice questions, it is completely OK.

A second way to make something fun out of her boring answers is this:

“You have 10 euros for your dinner here in [your city here] What do you buy?”


“You are not the type who will give all the cliché answers, are you? Spaghetti as favorite food, a sunny beach as a favorite holiday destination, and a cat as a favorite animal?”

(a bit hard maybe this tease, but it makes the lesson clear)

If you find that she is someone who gives shorter answers, tease her on her answers.

This way you will immediately stay out of the friend zone.

And if you play it well, you will enter the coitus zone.

That happens to be my favorite vacation destination.

Fancy some more fun questions?

Funny questions to flirt with her

A while ago, my friend Louis’s pretty face appeared beside mine on the site of the Telegraaf (a Dutch newspaper).

“Prehistoric pickup trick works”
– De Telegraaf

Be assured our trick worked. This is how it goes:

You approach a woman and asked her for advice.

You say you saw a woman which you’d like to get to know and flirt with… but you don’t know what to say to her.

You then listen to the woman’s advice and leave.

A few seconds later you (or a wingman) comes from behind the corner, and uses her advice exactly on her own.

The women loved it and we laughed a lot all day.

The best thing about this technique is that you can do something similar during your date.

You ask her one of the following 4 nice questions, and then use the advice on her.

  1. In what way could you fall in love with a man in one fell swoop?
  2. You know, I have a girlfriend, just friendly, we did flirt a bit and now she says she’s fallen in love – but I just want to stay friends. How would you handle that?
  3. I have been told today that a good friend with whom I have played football is gay. And he also appears to be in love with me. But I love women and it’s a very good friend of mine and I don’t want to hurt him. What would you do?
  4. Suppose you are cheating on someone, but you do it nicely with a condom. Which flowers would you best buy to make it up?

The first question from this list is definitely a good one. You learn to understand her (and other women) better. You can then subtly process that info in your date.

The second question is a bit of a sneaky old-school seduction trick. By telling stories about other women who fall for you, you have to be fun. Others choose you, so why should she not choose you?

The third question does exactly the same. Only men fall for you. Whether you want to make it even cooler or just a bit gay, you have to know for yourself.

The fourth question uuuuhm … you might not want to ask that, unless she really likes douchebags / assholes.

10 Questions to ask your tinder date

In the intro of this article I told you that there are better questions than:

  • Coffee or tea?
  • Dogs or cats?
  • Red or white wine?

There certainly are. And you get them now.

The “… or …” format is very nice for questions.

You give your date a simple choice and let her make the decision.

Only we don’t go for “dogs or cats” because she has heard that stuff 69 times.

How about these 10 pearls:

  1. Immortality or invisibility?
  2. Sunrise or sunset?
  3. Peanut butter with or without nuts?
  4. Are you a morning person or an evening person?
  5. Never again coffee or snacks during the film?
  6. Would you rather make a trip around the world or stay on a deserted island?
  7. Have you ever done bungee jumping?
  8. What was the last movie that made you cry?
  9. Who is your biggest example?
  10. Would you rather be a famous movie star or date a famous movie star?

Of course, I’m not saying you should spend the entire date asking each of these questions in a row.

You also want to come up with interesting topics to make the date memorable.

Guess what? There’s an article about this, so I suggest you check it out:

>> 15 Best Topics to Talk About with a Girl (Texting/Dates/Tinder)

Always a nice questionnaire in your pocket

Maybe you will go on 69 dates a week soon.

Then you will always be able to use extra questions.

I have two tools to provide you with extra material.

The first is the Facebook page Dilemmarama

It presents you with a new dilemma every Tuesday.

You can then simply borrow that dilemma and present it to your date.

Such as this for example:

If you do not want to stay alone forever, then choose option 1 in this case.


This page gives you a fun question every week.

You can’t wait a week every time?

Or do you need the really powerful stuff that makes women more obsessed with you than the Overly Attached Girlfriend meme?

Then take a look at my free Transformation Kit. 

It’s a toolkit to start dating right away.

In short: It teaches how to become attractive.

You get:

  • Step-by-step instructions for attracting women
  • How to get out of the friendzone and be her lover (eBook)
  • Steal my 25+ lines for more entertaining conversations online and offline
  • And much more…

Download it here, it’s free!

Have fun with all your new fun questions and other tools.

I’ll see you soon in the next article.

Your bro,
Dan de Ram

Stop awkward conversations
and painful rejections

My free Transformation Kit will make you irresistible to women.

  • 12 Opening Lines that Actually Work
  • 5 Date Generating Texting Tips (Plus Copy-Paste Lines for Tinder)
  • The Friendzone Escape-Room Trick
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