145+ Must Have Date Questions to Vibe Deep into the Night

date questions

“Hey, did you do anything exciting today?”

This is going to be the question you start your dates with from now on.

I will tell you more about why this is going to be your go-to question later.

What I can reveal, is that there’s a ton of verified studies to back me up on this.

I’m going to give you some more questions, so you’ll know what to say in any situation.

This is not a place for standard, run-of-the-mill questions.


Because they won’t get you anywhere when you’re on a date.

I want to give you the results.

And you will only get results if you’re not afraid to stray off the beaten path.

That is why I’m giving you:

  • 145+ date questions to ask a girl and make her crazy about you
  • The best date ice breaker questions to hit the ground running
  • How a small change in topic instantly increases your chances for another date by 50%
  • How specific use of words will have her drooling over you
  • Date questions for couples that want to deepen their connection
  • Juicy date questions to build the attractive tension
  • Which topics will create a deep connection between you; verified from several studies
  • In short: Date questions ranging from fun, interesting, deep, warm, hot to xxx

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.

Ask these date icebreaker questions to hit the ground running

“What’s the most fun thing you did today?”

“What are you looking forward to next week?”

“What is the best thing you had to eat lately?”

“What do you like best about this city (or the place you’re meeting)?”

“What cool thing have you always wanted to do here?”

That might lead you to think…

Why are these the questions I should ask her at the start of the date, Dan?”

I’ll tell you.

By the way…

Are you looking for more general get to know you better questions? And get all kinds of tips on how to keep the conversation going, how you can simply touch on all kinds of subjects, and how you can create a deeper connection?

Then check out this article:

-> The 131 Least Boring Questions Ever to Ask Your Date

Why a specific choice of words is important in your date quizzes

The words you use at the start of the date determine half of how curious she’ll be about you during the rest of the date.

You’ll hear dating coaches say things like:

It doesn’t matter ‘what’ you say…It’s about ‘how’ you say it.

They’re right.

But it’s only 50% of the truth.

The literal words is the other 50%.

So if you only take the advice of these dating coaches, you’re selling yourself short.

A date isn’t a game of golf, where a good player needs to use fewer strokes to get through the course than a player who isn’t as good, in order to make it ‘fair’.


A date is about results. And every advantage you can give yourself, you want to give yourself.

What exactly am I talking about…?

There have been studies into conversation starters at a giant networking event. They looked at the effect certain types of conversation starters had on the other person.

They found roughly two types.

  • The bad conversation starter, where the other person answers carefully, gives a tense smile and shuffles back and forth a little because of the awkwardness
  • The good conversation starter, causing the other person to smile, turn towards the other person and where the conversation goes increasingly louder as time passes.

Bad starters included:

  • What do you do for a living?
  • How are you?
  • Where are you from?

 Good starters included:

  • Have you been working on anything exciting lately?
  • Do you have a vacation planned anytime soon?
  • Has anything positive happened to you today?

Why did these lead to positive reactions?

Choice of words.

They used words that activate the brain to think of something positive.  

And when the brain thinks of something positive, it produces a neurotransmitter called dopamine.

Science shows that it’s released when someone experiences joy and reward.

And when it comes to a date, the release of dopamine in the other person does two things for you:

  • The other person experiences joy. You literally ask them to borrow excitement from somewhere else at some other time in their life and transport it to this situation.
  • It makes YOU more memorable. They will have more trouble remembering others. Every shot of dopamine is like a post-it that is made reminding them of someone else. And all these post-its are signed by you.

So ban the standard date questions from your arsenal and start working on questions with words that make the other person think of something positive.

Now before we jump into the fun, interesting and juicy questions you want to be asking on your dates. First 5 topics of questions you want to leave out of your date question ‘game’.

5 Question topics you want to avoid like crack dealers

Bring up these subjects, and I guarantee that you’ll be going home alone.

A date is not a debate room

Donald Trump and Boris Johnson will not be your best wingmen.

Avoid political date questions. Definitely at the start of the date. Or if you have just started dating.

Leave the negativity at your doorstep

Never bring negativity to a date.

If you’re negative, she’ll be negative.

So don’t talk about your exhausting week, shitty chores, or that you’re dreading having to clean your toilet.

Always focus on the positive vibes. Or turn something negative into funny (positive) story.

D0n’t pl4y w1th numb3rs

“How many dates have you had recently?”

“How long have you been single?”

“How many matches are you chatting with?”

  • Do NOT ask these questions.

They will make you look weaker than soft boiled pasta.

You’re an attractive maddafakka, and this so-called ‘competition’ isn’t even in the same ballpark as you.

Leave your parents out of it

I‘m sure you love your mother, dearly.

But bringing her up on your first date might come across a little childish.

It might also give her the impression that you’re looking to settle down fast. This can put too much pressure on her too soon.

The best thing is not to talk about your parents on the first date.


Unless she asks about your family.

Then you want to tell her a funny story, that makes you look good and which shows you have a nice family.

Let your ex be an ex-topic

Just like you and her ex are behind you…

You should leave this topic behind you on your date.

It’s about your current relationship. Not your past relationships.

Again, as with the parents when she asks tell something about it. And keep it lightheartedly.


Now that it’s clear what to avoid. Let’s start off with questions when you’re just getting to know someone.

Date questions to get to know someone

It’s always a matter of reading the room in the beginning.

Both of you are trying to figure out what you’re working with.

That is why at the start of the date, you don’t want to go too hard in terms of the types of questions to ask a girl.

The questions below are a perfect way to build up to more exotic grounds when it comes to date questions:

“Did you meet someone this year that changed you in some way?”

“Can you show me your life in 5 pictures?”

“Can you describe yourself in 5 words?”

“Can you describe me in 5 words?”

“What would you do if you had no choice but to spend 100€ every single day? No more, no less.”

“Which story about you does your family like to tell?”

“What was the most painful moment in your life?”

“If you could rule the world, what would you do?”

“Hawaii or Alaska?”

“Which words do you think should be banned?”

“Which habit would you want to get rid of?”

“Which habit makes you special?”

What did you always want to be as a child?

“What’s the most romantic thing anyone has ever done for you?”

“Which body part do you get complimented on the most?”

“Describe your first school bag, including what was in it?”

“What’s your favorite word?”

“What’s your nickname?”

“What place would you take me to?”

“Do you wear more or less lipstick to date if you think kissing might be on the table?”

“Which question would you prefer not to answer?”

“Which rule do you MAKE yourself follow?”

“What’s a great lesson you took from a book?”

“What’s a great lesson you took from a movie?”

“Wanna marry?”

“How do you feel about social media?”

“What is the most romantic way you would want to meet someone?”

“Would you be able to kiss someone you don’t know within a minute of meeting them?”


Now, you might be on a date with a girl who’s not talkative at all. She might be shy, or just a quiet person.

Regardless, if this happens, you’ll also need some tips on how to keep the conversation flowing.

Check out this article:

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

Fun date questions

A date is not about discovering every little fact about the other person.

You probably aren’t even super interested in what she does, studies, does daily or what she eats for breakfast in the morning.

You probably ask these questions to fill the silence or because you think that’s what you’re supposed to do.

You’re probably way more interested in how you feel with the other person.

A date is bout experiencing each other.

The best way to do that is with humor.

So ask these fun date questions:

“Is a turtle without a shell homeless or naked?”

“How do you find out whether a word is misspelled in the dictionary?”

“If honesty is a key, is lying the key to another lock?”

“A person with multiple personality disorder is about to kill themselves. Is that a hostage situation?”

“Do you think you could get a sock in your mouth, without using your hands or feet?”

“Say you had to be a teacher, what subject would you choose? It can be ANYTHING!”

“What would you do if you could be invisible for a day?”

“If you need a ride at 3 am, who do you call?”

“Who would give up their kidney for you?”

“You might actually be a robot… would you want to know?”

“Would you prefer a cat that acts like a dog, or a dog that acts like a cat?”

“Would you rather swim 100 meters through poop or through dead bodies?”

“Would you rather someone doesn’t show up at your wedding or to your funeral?”

“Free internet wherever you are, or free coffee/tea wherever you are?”

“Which body part do you most compliment others on?”

“What is the most hilarious title of a porno you’ve ever seen?”

Stray off the beaten path and make her feel attracted to you

Research by none other than Dan Ariely (love the name bro) has shown that it’s better to skip the standard questions and immediately ask whether she’s ever had an STD.

Sounds risky.

But his research has shown that there is a more positive response to the types of questions that are ‘out of the box’ than ‘inside the box’.

It turned out people were happier about these types of questions than about the safe date questions.

So skip the boring questions about her favorite color and favorite animal and use the following date question to ask a girl:

“The last time your relationship ended, how did that go?”

“What’s the most controversial thing about you?”

“Would you be able to blame someone else for a major crime?”

Do you want a free e-Book with 17 example sentences to spice up any conversation?

Then download it here:

Say goodbye to boring conversations with the Boring Conversations Cheat Sheet.

Subtle date questions to ask a girl that could be taken the ‘wrong’ way

You’ll understand what I mean with ‘wrong’:

“Bottom lip or upper lip?”

“Left or right-handed?”

“Top or bottom?”

“Hard or soft?”

“Would you rather have someone between your legs, or would you rather sit between someone else’s legs?”

Later on you’ll find some more juicy date questions. You definitely have to ask a few spicy ones to let her know you’re not asking to be in her friendzone.

Date questions for couples-to-be

These date questions can make her feel like you’ve been together forever.

It creates a very flirtatious vibe between you. As if you’ve been a couple for quite some time.

Exactly the feeling you want on a date:

“Do you remember when we were walking by the sea at sunset? I grabbed both your hands and kissed you on the mouth?”

“Can you remember our first kiss along the Amsterdam canals?”

“Do you remember that we went to the pet store to pick a pet? You wanted a cat, but I preferred a dog?”

“Do you remember the first time we met up? We were at this cute little place. When we got our drinks, we toasted and looked into each other’s eyes in silence?”

“Can you remember that we went to the park, it started raining halfway through and we had to cuddle up really close because we only had one umbrella?”

I also have an article with first date questions that will help you get her to fall in love with you from the very first date:

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

Ask about other dates to make yourself more attractive with these date night questions

It’s always hilarious to talk about other dates.

It also gives you an opportunity to find out a lot about her…

…what she likes and what she sees as deal-breakers.

That way you can make yourself look really good:

“What’s the worst date you’ve ever been on?”

“Have you ever met up with someone from Tinder who turned out to look completely different than his profile pic?”

“Have you ever met someone that you basically fell in love with on the first date, but that you couldn’t stand the second time around?”

“What’s the biggest lie you’ve told on a date?”

“What do you pay attention to when you’re on a date with someone?”

“What was your best date ever?”

“Which date were you most nervous about?”

“What was the best location for a date you’ve been to?”

“Do you pay more attention to what you say during a date?”

“Do you put extra time into your appearance before going on a date?”

“How do you prepare for a date?”

If you don’t want to just lean on questions, but also make bold statements about her, making her feel instantly attracted to you…

Then steal the best way to prep for a date from me.

Check out my Transformation Kit.

Create massive connection with these great date questions

Research shows you can create an instant connection with your date by exposing secrets.

Sounds nerve-wracking?

Yeah, I guess you’re right.

But it also creates a connection between the two of you which would take ages to form through other standard date questions.

Now you can forge it with just a few questions.

These are often questions that bring up tons of stories.

Do be careful, though.

You’re asking her to spill a secret. Chances are you’ll need to unveil something too.

And to ease her into it and make sure she doesn’t jump up and spill her hot coffee on you, maybe its best you tell your secret first.

So next time you’re on a date, try asking one of the following questions:

“Have you ever done something wrong, but no one ever found out?”

“Do you ever tell your family that you love them?”

“What’s the biggest lie that you continue to keep?”

Date questions you definitely want to ask your girl

”Did you ever go through something that you thought would end really badly, but that turned out really positive?”

”What makes you nervous?”

”Which New Year’s resolutions did you actually keep?”

”Would you want to change your name?”

”Would you want to change anything about yourself?”

”Which household task are you the master of?”

”What was your first impression of me?”

”Do you have the guts to compliment random people in the street?”

”How do you flirt with someone, verbally?”

”How do you flirt with someone, non-verbally?”

”What is the most unexpected thing you’ve learned along the way?”

”If you could call yourself, 5 years ago, what would you tell yourself?”

”What would you do with your time if you could afford to quit your job or your studies?”

”What do you believe in that no one else that you’ve met so far believes in?”

”Someone gets a WhatsApp message from you, but they’re not sure it’s you, and they’re worried. They think your phone might be stolen. What could they ask you to find out if it’s really you?”

”Are you working on projects that relate to your passion right now?”

”What’s the best gift anyone has ever given you? Or that you gave TO someone?”

”I read/saw this (replace ‘this’ with something you read/saw) the other day, what do you think?”

”Is there anything you don’t eat?”

”What type of vacations do you enjoy?”

”Has anything surprising happened today?”

”What is the best advice anyone has ever given you?”

”What were you like as a child?”

”Have you been to any good restaurants lately?”

An original date means half the work

The more original your date…

The less work you’ll have to do.

So check out this list of original date locations. You can find something original to do wherever you are.

Check out the article on unique dating locations here:

-> 35 Exciting Date Ideas: How to Have an Unforgettable Date

Date questions to get to know someone better

“If you could go back in time and relive one of your childhood years, which one would it be?”

“If money wasn’t an issue, which career would you choose?”

“If you could know exactly what your life is going to look like for the next ten years. What would you want to know?”

“If Hogwarts is real and you get a letter. Would you go?”

“Which decision in your life would you like to retake?”

“To what unsolved mystery would you want to know the answer?”

Which one of your senses could you do without?

“At what Olympic sport would you want a gold medal?”

“Which TV show or movie would you want to be a writer?”

“Which body part would you sacrifice if it meant you could cure cancer?”

Follow up to the previous one:

“Would you still do it if no one ever knew you were the reason they found the cure?”

“If you could only have one type of drink in addition to water, what would it be?”

“Which superpower would you want to have?”

“Let’s say you can’t be in touch with someone you love for a year, who would it be?”

“If someone pays you a million euros to wear the same type of clothing forever, would you do it?”

“If you had to live in one place for the rest of your life, where would that be?”

“If you could only use one swear word for the rest of your life, what would it be?”

“Which animal would you like to be able to talk to?”

“Which celebrity that is of the same sex as you, would you want to marry?”

“Shower, brush your teeth, and wash your clothes. You can only pick two… you can NEVER do the other one again. Which ones?”

These great date questions for couples too.

Even if you’ve been together for quite a while, there are still more layers to discover about a person.

Someone keeps evolving throughout her life. There’s always another layer to discover. This doesn’t only keep your relationship interesting. It also keeps you interested in each other.

Let’s continue with one specific date question you could better avoid.

Rather avoid this date question topic

Mr. Wiseman’s research shows that it’s better to skip the topic of ‘movies’ in a conversation.

It’s better to talk about traveling.

This increases the likelihood of a second date by 50%.

Talking about movies usually happens in terms of ‘good’ or ‘not good’.

And might have negative connotations: if she’s totally addicted to Harry Potter, and you think it’s just a cheap Lord of the Rings knock-off.

And everyone loves talking about their travel stories or future adventures.

So stop talking about movies and start talking about traveling.

For example:

“Would you want to travel alone?”

“Which country do you dream of visiting?”

“How long could you be away from home?”

Up until now, the questions have been friendly.

Nothing bad with friendly since all of them are fun to ask and really get to know someone better.

However, to really get the sparks flying between you, you might want to go a little more spicy.

Up next are these juicy questions:

Juicy date questions

To make sure she doesn’t think about putting you straight into the friend zone, you want to throw in at least one sexual innuendo.

It might be a little too forward to ask her what her favorite position is though.

So it’s better to be more subtle about it, but no less effective. Use these juicy date questions:

“If I decided to never shave again, anywhere, would you still want to sleep with me?”

“What if I had a condition that prevented me from having sex, how would you pamper me?”

“If you could be a man for one day, what would you look like and what’s the first thing you’d do?”

“Have you ever watched another couple have sex? Did you see it on purpose or by accident? ”

“Do you undress man’s torso first, or do you go straight for the pants? What about yourself?”

“What is your secret way to turn a man on?”

“Best place you’ve had sex?”

“Weirdest place you’ve had sex?”

“Biggest age difference you’ve kissed?”

“Biggest age difference you’ve had sex with?”

Hey, it goes without saying, but you shouldn’t spend the entire date asking each of these questions in a row.

If you want to make the date memorable, you also want to come up with interesting topics to talk about.

Guess what? There’s an article about this. Check it out:

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

Date questions to find out what she’s willing to do for you

These questions are fun for a little further on during your date.

They will indirectly tell you how much she cares about you.

And how much she would be willing to do for you right at that moment.

“Would you kill someone if it meant saving my life?”

“If your favorite celebrity would want to marry you, would you dump me?”

“If I get kidnapped by aliens, how long would you wait before you start dating someone else?”

“If I kill someone, would you help me hide the body?”

“How much money would it take for you to dump me? 1 million? 10 million?”

“If you could live forever, would you? Even if I would die when I was 100?”

“Would you take a bullet for me? ”

“If you could make one wish, would you wish I was with you?”

“If I am allergic to cats and dogs; would you get rid of them if you had one?”

“Say you’ve got superpowers, but you’re not supposed to tell anyone. Would you secretly tell me?”

Date questions and answers – A final bit of advice for you

Date questions done!

But be careful!

It’s not smart to ask them all one by one, like a gate that only lets one person through at a time.

That will come across super weird, and you will end up in the biggest pitfall where 9 out of 10 men already end up anyway:

The interview date.


You want to come prepared.

And reading this article has been your preparation.

But you want to sprinkle these date questions through your date like you’d do with herbs and spices through your food.

Remember the questions you like and what you really want to know about her.

Write them in the notes section of your phone. That way you can always check them really quickly if needs be.

There’s one more advice I want to give you.

It helps to get better at meeting women in every arena.

  • Conversation techniques that would make a glass of water wet for you
  • Sentences that will get you out of any compromising situation
  • And tips for online dating, making sure your phone is constantly vibrating off the table with feminine interest.

The Transformation Kit.

Free for you.

All you have to do is press the button and leave your email address.

I’ll do the rest for you.

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
Yes, give me the Transformation Kit!

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