Being playful and fun is great, but there are times when being serious makes more sense than laughing about stupid jokes and pranking each other with whoopee cushions.

There will come the time when asking a girl deep questions is the start of a wonderful relationship.
Don’t get me wrong. Talking about fun and naughty topics is an essential part of the seduction process. You can use those topics to loosen up the atmosphere, to make her smile and to make her horny. With some girls, you’ll never talk about anything else than sex positions and inappropriate jokes.

These girls have the potential to be a memorable one nightstand. However, it is highly unlikely that you’ll end up in a meaningful and exciting relationship with a girl who you never asked anything deeper than “do you prefer How I Met Your Mother or Two and A Half Men?”

If you really want to have a meaningful relationship with a girl, you should find out more about her than her most favourite TV show. If you meet a special girl who is really important to you, you want to be able to dig deeper than that.

I forgive you if you only scratch on the surface when you talk to someone you don’t spend more than 24 hours with, but if you meet a girl who you really care about, scratching on the surface is the biggest mistake you can possibly make.

You deserve to find out who she really is and she deserves a man who wants to find out the same about her.

What are some deep questions to ask a girl that help you to immerse in her world and to find out what she loves, what she hates and who she really is?

Well, asking her where she works and how long it took her to get her Master’s Degree is not the type of questions that make her heart thump. Unfortunately, that’s the kind of logical diarrhoea that most guys tend to ask women when they try to “seduce” them.

Sorry bro, but getting all logical and asking her about the dull things she does at work all day, won’t make her think about you when she is masturbating.

Unless you want her to think “oh, another boring idiot”, you should ask her more meaningful things. Ask her questions that trigger some pretty powerful emotions. Show her that you care about her and her opinion. Make her feel special and understood. Communicate that you want to find out everything about her and that you want to go beneath the surface.

If you do that, she’ll think to herself:

“He’s incredible. I have never met a guy who asked me that. He’s the first guy who gives me the feeling that he really cares about me. I don’t know how that’s possible, but I have the feeling that I am falling for him.”

Let’s have a look at all the deep questions to ask a girl that will make her think that you are that special someone.
1. If you could be anywhere now, where would you be?

This is an amazing deep question to ask a girl who is on a date with you. If she really likes you, or if she pretends to like you before she tries to stab you with her eyeliner pencil, she will say that she wants to be here with you and nowhere else.
run-down apartment

If this is the place she wants to be, you should think twice before you put a ring on her finger

In case she really says that she just wants to be here, you can change the question a little bit. Ask her about the country, the place and the environment she wants to be in.

This can tell you a lot about her personality.

A girl who says that she sees herself in a shopping boutique in the centre of London has a completely different personality than a girl who sees herself at a lonely beach on a small island. This question allows you to find out where she wants to live and how she wants to live.

However, if you ask your long-term girlfriend this question and she answers “far, far away from you”, you have a serious problem.

2. What are you afraid of the most?

Asking a woman about her deepest fears can help you immensely to understand her better. It also shows you whether or not you are dating an idiot or a girl who has more brain cells than Jessica Simpson.

“I am so afraid of the day when they stop showing INSERT SENSELESS TV SHOW HERE. I will literally kill myself when that happens.”

“I think the biggest fear that I have is that my family members suffer and that I can’t help them.”

I hope you see the difference between the answers and I also hope that you run as fast as you can whenever you meet a girl who would literally kill herself because of a freaking TV show.

3. What would you have to see to cry tears of joy?

When I am on a date with a girl I want to find out if she is empathic. The last thing I want is to date a logical and cold-hearted robot. If I would want that I could have stayed in Germany. I want to date women who are emotional, empathic and who are deeply connected to their emotions.

If you ask a woman this question and she can’t think of anything that would touch her enough to make her cry tears of joy, you should be suspicious.

This was the answer to my girlfriend when I asked her this question:

“Seeing the sparkling eyes of young street children after giving them enough food for the day has the power to make me cry tears of joy.”

Now you know why I am together with her.

4. Are you a spiritual person?

Okay, maybe spirituality is not really important to you but for me, this is still one of the most important deep questions to ask a girl. I am a very spiritual person, I try to meditate as often as possible and I love to do some weird yoga positions in nature.
girl doing yoga

She’s the kind of girl I like

For me, the girl who I share a bed with must be open for spirituality.

That doesn’t mean that I want her to believe the same things as I believe. All I want is that she is open to it and that she doesn’t judge me for being the weirdo that I am.

In case you are deeply religious and you hope that I burn in hell for being spiritual, you can, of course, change your question and ask her about her beliefs. Talking about religious topics isn’t the sexiest thing on earth, but if you are deeply religious you might want to find out if your potential wife believes in the same imaginary friend as you.

5. What is your biggest passion?

I know that this is such a cliché question. Nowadays everybody is talking about following your passion and about living a passionate life. Even though a lot of people use this word more frequently than toilet paper, it is still a good thing to ask.

To enjoy a harmonic relationship with a girl you need to have similar passions.

I know about the saying that opposites attract each other and I don’t doubt that being a little bit different can be very appealing. However, I believe and know from my own experience, that a relationship between a girl who loves to go shopping all day and a guy who dedicates his life to minimalism and anti-consumerism won’t last that long.

Find out about her passions and you’ll find out if she has girlfriend potential or not.

6. How do you think about materialism/consumerism?

This is a very important question, at least for me. In case you are the kind of guy who wants to hang out with gold diggers and with girls who rinse you, you can of course ignore this topic. However, due to the fact that you are one of my loyal and intelligent readers, I doubt that you are that stupid.

It’s absolutely okay to ask the girl you are dating how she thinks about materialism and consumerism.

I have been on quite a few dates with girls who told me that owning status symbols is very important for them and that they only buy clothes from expensive brands.

I was so thankful for their honesty. Now that I knew that they were superficial girlies with low self-esteem, I could delete their numbers out of my phone.

7. How regularly do you see your best friends?

Friendship is incredibly important to me. Of course, I can’t see my friends every week, especially when I am travelling all over Asia while they are in my tiny home town. Nevertheless, I always try to stay in contact with them and I try to visit them whenever I am in German territory.

If friendship is important to you, I assume that your girlfriend should have the same attitude.

Why would you want to waste your precious time with women who don’t give a fuck about their friends?

A girl who doesn’t care about her friends also doesn’t care about the other people in her life, such as her family members and you. You are way better off finding a girl who values friendship as much as you do.

8. Imagine yourself in twenty years. What do you see?

Even though I hated this question so much whenever I went to a job interview, it can reveal a lot about a person when you ask it the right way.

Don’t put her under pressure.

Invite her to close her eyes and to imagine herself in twenty years.
I think I don’t have to tell you what you should do if this is where she sees herself in 20 years…

I think I don’t have to tell you what you should do if this is where she sees herself in 20 years…

In case you want to have fun with her for a couple of nights you should be happy if she says that she still sees herself partying and travelling the world. In case you are looking for a girl who you end up marrying and starting a family with, you’ll be a lot happier when she says that she sees herself in a nice house with two children and a loving husband.

This is one of the deep questions to ask a girl that has the power to immediately see if she is a good fit or not. If the way you imagine your future is in alignment with how she sees her future, you might want to think about a future together.

9. What is the meaning of life?

It sounds cheesy, but it is so incredibly helpful to find out if a girl is a perfect fit, or absolutely not your type.

I believe that the meaning of life is to follow your heart, to do what you love and to have fun along the way.

What if a girl thinks that the meaning of life is to suffer until you are retired? Well, then she definitely doesn’t belong to the group of girls I want to put my penis in.

If you think that the meaning of life is to have fun and to do whatever you want to do, you’ll be damn unhappy when you waste your time with a girl who thinks that laughing is for stupid people.

If you share the same meaning, you can share the same life.

10. Have you ever loved someone?

As I wrote down in the ten random facts about me that you can read on my about page, I believe that love is an essential part of every human being’s life. Believe me when I say that you should better date a girl who knows how to love, than a girl who has never felt what it means to love someone.

I have dated girls who weren’t able to love and I wouldn’t do it again. They tend to have more emotional issues than a child actor on heroin and if you ever fall in love with them you are basically fucked.


Because she won’t love you back.

Look for a girl who has at least a loving relationship with her mother or father. In case her parents didn’t teach her how to laugh, she will have a hard time learning it from you.
mother with daughter

That’s the kind of mother-daughter relationship you are looking for

11. What would you do differently if you could turn back time?

Is there something she regrets? Is there something that she did in the past that she would have done differently? These are great deep questions to ask a girl.

If she has no regrets, you can assume that she lives in alignment with her own values.

Maybe she did something that she regrets. If she tells you what it is you can show her that you respect the fact that this experience helped her to grow and that she sees things differently today.

I once met a girl who told me on our first date that she cheated on her ex-boyfriend and that she regrets it. I appreciated her honesty, but as you can imagine I didn’t put her in the category “possible girlfriend”.

12. What’s your secret?

Everyone has a little secret. There is always something that you don’t want other people to know. You have it, I have it and the girls you are dating have it. I reveal a lot about myself, but I also have some secrets that I don’t want everyone to know.

What is it for the girl who you want to seduce?

It’s your job to find it out and the best way to do that is by asking her.

Even though a woman usually doesn’t want to reveal her secrets, a seductive voice and a deep look into her eyes can work miracles. If you ask her in a romantic atmosphere, she will tell you everything you want to know.

One girl who I went on a few dates with told me that she once threw a television on her boyfriend. That was the moment when I decided that it was time to go on the run.

13. What is the hardest lesson you had to learn in life?

Sometimes life is hard. Sometimes you get knocked down and sometimes you have days where you just want to give up. Of course, those days are painful, but those are also the days that make you stronger and teach you a lot about yourself.
sad woman

“One day I coloured my hair and I wanted them to be blonde, now they are red…I learned it the hard way to look at the packing…”

For me, the hardest lesson that I had to learn was when I was basically thrown out of a company, because I was suffering the typical “I am a special snowflake” syndrome that’s so popular among my generation, instead of working my ass off.

This taught me a lot about work ethic, my self-perception and my own ego.

Whenever I met a girl who I am really interested in, I love to find out about her struggles and her development. If you meet a girl who refuses to learn from her failures and who is immune to personal development, you’ll most likely date a very stubborn person.

14. What did you want to be when you were 5 years old?

Unless the girl you are dating got abused by her father and nearly aborted by her mother, she has at least one or two positive childhood memories. When we think about our childhood we usually think of freedom, fun and crazy dreams. These are the feelings that you want her to feel when she is together with you.

These are the feelings that make her feel alive and carefree.

A woman who links those emotions to you will immerse in the seduction process without any resistance.

That’s why it is your job to ask her about her childhood and to find out about the crazy dreams she had. Look her deep into the eyes while she tells you that she wanted to be a princess when she was five and enjoy her warm smile.

15. Who influenced you the most in life and why?

I absolutely love this question. We all have one or two people in our life that had a major influence on our preferences, our beliefs and the way we want to design our life.

For me, this person is my grandmother.

We think the same, we laugh about the same jokes and the fact that she lived in Asia for over a decade inspired me to travel there and to fall in love with the country and the local women.

One the one hand, this question allows you to connect with her on a higher level, by showing that you are interested in the person who smoothed her way. On the other hand, you find out about her relationship to her family (in case she was influenced by a family member) and you find out which path she is on and where she is heading to.

16. Is there something you stopped doing, even though you love it?

This is definitely one of the deep questions to ask a girl when you want to find out about her dreams, her interests and her desires. There are already enough people on this earth who stopped doing what they love, just to end up as miserable hamsters in a wheel they don’t want to be in.

Find out if she is one of them.

Why should you do that? Well, being together with a girl who is determined enough to do the things she loves is far more exciting than being together with a girl who stopped doing the things she loves, just because life got in the way.

17. What do you want to do before you die?

Do you have a bucket list? I have one and one of the things that I want to do before I die (besides having as much sex as possible) is to visit every continent on this earth.
moody harbour

What does she want to do before the sun goes down?

Whenever someone asks me about all the things that I want to do before I die, I instantly feel a connection with this person. When I tested this question on dates with girls, I could observe the same effect.

The reason why I think that this question is so effective for the connection between two human beings is that it shows us our own mortality, while it triggers a spirit of adventure and thirst for action.

Her next action could be to jump in bed with you.

18. What would you do today, if you would know that you are going to die tomorrow?

This one also belongs to the deep questions to ask a girl that mix the mortality factor with the desire to take action and to live life to the fullest. I think I don’t have to tell you why it is helpful to motivate a girl to live her life to the fullest.

As soon as she starts to think about the fact that she could die tomorrow, she’ll think about all the fun and exciting things she could do today.

What if there would be no consequences?

Well, then she would jump in bed with you without even worrying that you or anyone else could label her as a slut.

All you do with this question is to make sure that she follows her desire to take action.

19. What do you value the most?

Everyone has certain values that he or she lives by, even if they only exist in our unconsciousness.

You have values, I have values and the girl you are dating has them too.

Due to the fact that you are reading this article, I assume that honesty is an important value for you. Unless you want to date a girl who lies to you and cheats behind your back, you probably want her to value honesty in the same way as you value it.

What do you do if the girl you are dating values her fur coat the most?

In this case, you should say that you value the poor animals that had to die for it before you leave her.

20. How is your relationship with your father?

This is one of the most important deep questions to ask a girl. There are so many girls out there who have severe father issues and who start to hiss as soon as you mention the name of their daddy.

It is highly unlikely that such a girl has a positive attitude towards men in general.

My girlfriend has an extremely good relationship with her father. I see this as the main reason why she isn’t one of those hardcore feminists who hate men. A woman who loves her dad learned from a young age that men are good.

This woman has absolutely no reason to hate men.

From all the girls I dated who had father issues (I was young and needed the pussy) there was not one girl who was girlfriend material. Those girls will never love you for the man you are because they never learned to love men.

21. What would you do with 1 million dollars?

In case you are familiar with my writing you know that I absolutely hate materialistic women who define themselves through brands and superficial stuff that nobody needs.

I want women who rather use their money for charity purposes than to buy a handbag for $1000.

Do you want to end up in a relationship with a woman who is so superficial and so insecure that she needs designer clothes to feel valuable? No? Then ask her what she would do with 1 million dollars.
woman hugging car

Who gives a shit about dying children in warzones, as long as I have my cute white car!

A girl, who answers that she would save some money for bad times and help poor people with the rest, is definitely girlfriend material.

22. Do you have an Instagram account?

I have to admit that this is a personal topic. I can’t stand girls who upload ten pics per day on Instagram and I don’t only say this because I think that they are all semi-professional prostitutes, even though a lot of them are.

Girls who upload thousands of pictures of themselves in the hope to get some approval through followers and comments are anything but emotionally healthy.

If a girl seeks attention on social media, she’ll also seek attention in the real world.

You might be able to give her the attention that she needs for a certain amount of time, but the day will come when you are home alone, while she is in the club and some guy gives her compliments and one drink after another.

Guess what a loyal girl with high self-esteem would do and what a girl with self-confidence issues and an Instagram account would do?

23. If you could change one thing about yourself, what would it be?

This also belongs to the group of deep questions to ask a girl that is perfect when you want to find out if the girl you are with has healthy self-esteem or not.

I know that no woman on earth is 100% satisfied with the way she looks, but if a girl tells you that she would change her ass, her nose, her eyes, her lips, her belly, her legs and even her fingertips, you can confidently assume that she needs a good therapist instead of a plastic surgery.
cosmetic surgery

Do you really want to date her?

If she tells you that she thinks that her nose is a little bit too flat, but that she doesn’t see the need to change that, you can assume that she is not completely nuts.

24. What would you do tomorrow if you would become president today?

You only see the true nature of people when you give them power. Of course, you can’t help the girl of your dreams to become president (let me know if I am wrong), but you can at least ask her what she would do if she would be the president of her country.

This question will show you how creative, intelligent and how compassionate she is.

I once asked this question an American girl and she honestly told me that she would throw a nuclear bomb on the European continent, in order to finally win the war against terrorism.

I never called her again.

25. What is your most amazing memory?

Comfort is an extremely important part in every seduction process and in order to make a girl comfortable in your presence she has to feel good. If she feels good, she will automatically feel good about herself.

One way to make her feel good is by making her laugh and by doing exciting things with her. Another way is to make her remember all the exciting things that she already experienced.

Ask her about her most amazing memory and enjoy how her energy changes into a ray of positivity.

26. What are you grateful for?

I personally believe that you can only be truly happy in your life when you are grateful for what you have. I don’t say that you should stop improving yourself and that you should give up on your goals. Having goals and achieving what you want to achieve is absolutely essential for your personal fulfilment.

woman with shopping bags

If shopping is the only thing she is grateful for, you might want to look for a new girlfriend

However, a person who isn’t grateful for anything basically says:

“I am on the completely wrong path and I don’t really want to live the life I am living at the moment.”

I don’t know about you, but I don’t want to date such a girl.

27. What do you think happens after we die?

This is another deep question to ask a girl, especially if you are into spirituality. It’s quite interesting to ask a girl this question. Not because you hope to get the right answer (which doesn’t exist), but because it shows you if the girl you are with is willing to think about topics that go beyond TV shows and Iggy Azalea.

When it comes to this question there are only two types of girls.

On the one hand, there are the ones who never thought about it and who don’t really care. On the other hand, there are the ones who tell you that they have already thought about this topic before they start a long monologue.

Guess who’s the one with the higher IQ?

28. What would you do if you would be invisible?

This is a relatively fun question to ask and depending on her answer it can go really deep. All I would do if I would be visible would be to go in the girl’s locker room in my gym and to watch those sexy little things take a shower, but you might find a woman who is much more creative than me.

I once met a girl who told me that she would walk into banks, steal some money and give it to the poor. I was truly impressed by this answer. Maybe you are lucky and you also find a sexy Robin Hood with boobs.

29. What would you do if you would be famous?

There are two types of famous people. There are the ones who get crazy, who spend all their money on expensive toys and who take one drug after another. On the other hand, there are the ones who want to help people with their money and who want to use their fame to promote good and valuable projects.

Wouldn’t it be interesting to know what the girl of your dreams would do if she would be famous?

A girl who tells you that she would use her fame to advertise charity projects might be a better girlfriend than a girl who says that she would be happy to get designer clothes for free.

30. What advice would you give your younger self?

Self-improvement is an important aspect of my life. I want to spend time with people who want to improve themselves and I want to help you to improve yourself.

Due to the fact that destiny or Mother Google motivated you to click on this website, I assume that improving yourself is also a very important part of your life or at least an aspect that you plan to work on.

Why would you want to waste your time with women who don’t care about improving themselves?

A girl who is resistant to change won’t be able to answer this question, but a girl who is into self-improvement will be able to write a whole book about all the things she would tell her younger self.

Which of those girls do you want to date?

The choice, as always, is yours.

Summed Up Wisdom

This article is already long enough and listing all the questions again would make absolutely no sense. The conclusion for today’s article is this:

It took me hours to write down all the deep questions to ask a girl. The best way to reward me for the hours I spent writing it is to ask the next girl you go on a date with at least one of the questions I mentioned.

Connect with her on a deep level and make her happy. That makes me happy.



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