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100 Excellent Questions To Ask Your Girlfriend

Couple Holding, Romantic Questions to Ask Your Girlfriend

The most detailed questions to ask your girlfriend on the internet, complete with commentary.

When we created our comprehensive list of over 100 questions to ask a girl you like, we were careful to not to include certain questions that could be considered too intimate. That’s because questions that are appropriate for your girlfriend might not necessarily be appropriate for that cute girl you just met in accounting class.

Be that as it may, as integral as good communication is to any healthy relationship, many guys find it difficult to keep a conversation flowing even with women they’ve known for years, partly explaining why dating and relationships are on the decline and the divoice rate is through the roof.

The best way to truly know your girlfriend is to actively ask her questions. The more you get her to talk, the more you will learn, and the more likely your relationship will be healthy.

Keep reading for over 100 fun and engaging questions to ask your girlfriend, from the serious to the downright kinky. Not only will you learn more about her, but she’ll likely be flattered that you even asked!

Good Questions To Ask Your Girlfriend

Not only are the questions grouped into sections to make them easier to find, but we have also provided commentary on each one to give you an idea of  what to look for in an answer.

Make sure to pick and use the questions that you think are most useful or the circumstance. And don’t rush to end the relationship if you and your girlfriend disagree on a question.

Monitor the issue and see how much of an impact it has on the wellbeing of the relationship moving forward. Ask yourself: Is it benign or downright egregious?

Also, make sure to actively listen to her answer, and reflect on it without judgement. Active listening is the mark of a great man.

See: How To Be A Better Man: 40 Ways To Take Charge Of Your Life

10 Questions To Ask Your Girlfriend About The Future

If you want to know where your relationship is heading, this collection of questions to ask your girlfriend will help you determine if the two of you are on the same page and see if being together is still a good idea.

What would an average day in your perfect life look like? Do you have just one ideal life or can you think of more than one?

1. Take a minute, close your eyes and imagine what your perfect life would look like. Describe it in as much detail as possible.

How does her present life differ from her ideal life, and what is she doing now to change her present life to her perfect life? ​

This question is excellent for gauging what she wants in life and weather her desires and goals are aligned with yours. 

For example, if your perfect life is building and running a multinational business but her’s is to backpack around the world without a care in the world, you two have some talking to do.

2. What do you think the role of a woman in a relationship should be? How about the role of a man?

This can be one of the most toucy questions to ask your girlfriend, especially when considering the dramatic shift in gender and family roles. Are her views traditional or “progressive”?

Whatever her answer is, you’ll want to make sure you’re both in some sort of agreement before escalating the relationship any further.

3. How do you feel this relationship is going?

Open-ended questions like this one can be a goldmine when it comes to better communication in your relationship. Instead of restricting her answers, it allows her to freely express her thoughts.

To get the most out of it, don’t let her respond with “good,” and then just move on. Try to spark a back-and-forth conversation that objectively looks at where your relationship is heading and what improvements can be made.

4. What could we work on to improve our relationship?

This may seem like a scary question to ask your girlfriend, because it opens you up for criticism. But how can you gauge your relationship’s future if you’re not willing to really examine it?

It could go a long way to shed more light on an issue in your relationship that needs addressing or new skills that need to be learned.

For example, if she tells you that she finds you less attractive because you’ve put on weight, then you’ve just opened the door to solving it. On the other hand, if she brings up something totally unexpected, then it might be a sign that the two of you are not on the same page.

5. What do we argue about the most, and how can we fix specific issues so we don’t argue?

Arguing can be very uncomfortable, and talking about arguing can feel even more daunting. But arguments can ruin a relationship, which is why this is one of the most important questions to ask your girlfriend.

Figuring out why either one of you gets triggered by a certain problem, and figuring out how to address the problem, will save both of you time, stress, and anxiety down the line, and strengthen your relationship.

And if your girlfriend doesn’t want to have such a conversation, she’s probably not what you need in the long-run.

6. How Does It Make You Feel When We Argue?

This question about arguments in your relationship is more about feelings. Some people just love to argue, so asking her can help you see if she’s arguing just for the sake of winning or arguing because you’re arguing.

You may even be able to learn how she processes fights emotionally so that the two of you can develop tactics to prevent future arguments from escalating.

So if your girlfriend feels the way you do when you fight  (sad, anxious) , that’s probably a good sign. If she revels in it, run.

7. What would an average day in your perfect life look like? Do you have just one ideal life or can you think of more than one?

This is a variation of the previous question. No one’s life can ever be perfect, but it never hurts to dream, right?

There are so many potential components of an ideal life (people, interests and passions, livelihood, etc.), so she’ll probably have a lot to say. 

This series of lighthearted questions to ask your girlfriend, so periodically ask her to see if anything has changed and whether adjustments need to be made to the relationship. 

8. When do you want to take our relationship to the next level? What is the next level?

This is a big question to ask your girlfriend. Fortunately, it’s an open-ended question that will give her some wiggle room to express her thoughts. 

You will get an idea of how seriously she views the relationship and whether or not she is ready and serious enough to take things to the next level.

If talking about taking your relationship to the next level makes you nervous, just remember that you will have to eventually.

9. What Are Your Personal Thoughts On Kids?

If you have reached a point in your relationship where you’re asking this question, then the two of you are probably already on a solid footing. But even if your relationship is just getting off the ground, starting to think about a future with the possibility of children is very important.

There should never be an assumption that you or her want kids. You need to be on the same page so that you can plan accordingly.

For many couples, issues about having children is a deal breaker for whether or not to stay together. 

11 Questions To Ask Your Girlfriend About Her Past

Smiling nerdy young girl holding her books in school hall way.
How your girlfriend was when she was younger can tell you a lot about how she is now.

These might be the toughest kinds of questions to ask your girlfriend because they are deeply personal.

We all have baggage. And while you may think her baggage won’t affect you, or that you can leave the past in the past, the unfortunate truth is that unresolved issues from the past do ruin relationships — many relationships!

To get to really know your girlfriend, and particularly what she brings to the relationship, you will have to know where she came from, what she’s been through, and how even-keeled she is. These questions will help you do that.

1. What was your most serious relationship? How long did it last? Why did it end? What did you like or dislike about him?

First of all, try not to get jealous when she starts waxing poetic about her ex-boyfriends, OK? After all, you’ve probably also been around the dating block.

The purpose of this question is to learn about her dedication when in relationships and ability to accept responsibility for her mistakes, as well as how she handles conflict.

If you notice similarities between your partner’s descriptions of her past relationships and your relationship with her, it could indicate a pattern that may need to be addressed.

2. What was the best gift you’ve ever given to someone? What is the best gift you have ever received?

We all love receiving gifts, but not enough people like giving them.

These interesting questions to ask your girlfriend should give you some insight into how considerate and thoughtful she is of people, and what she values in people, things and experiences.

It’s also an excellent opportunity for her to brag about herself.

3. Have you ever cheated on someone before? What happened?

This can be a very touchy question to ask your girlfriend, so tread lightly.

That being said, cheating in relationships is so common that it’s a question worth asking. If she comes clean to you, try to find out why she did it, if she felt bad doing it, and whether or not she’s ever been cheated on.

Try to gauge how accountable, responsible, dedicated, and fair she was to the person she cheated on. After all, there is some truth to the old adage “once a cheater always a cheater.” If her reasons for cheating seem unreasonable, there is a good chance she will cheat on you.

4. How much time did you usually spend with ex-boyfriends? Did you think it was too much time, or not enough time? What did you usually do with your ex-boyfriends?

Once again, don’t be that guy who gets jealous over her girlfriends ex-boyfriends.

Some guys like their girlfriend to be around them all the time, while others prefer some distance. On the same note, some girls like spending as much time with their boyfriend as possible, while others don’t.

This series of questions to ask your girlfriend about her past should give you an idea of how much space you should be giving her.

5. Have you ever been in a relationship when you weren’t in love?

Dude, have you been dating a gold digger all this time? Is she only with you so that she can gain material benefits?

All jokes aside, if your relationship is just starting off and you still don’t know her that well, a question like this can give you a peek into her motives.

But don’t be quick to cast judgment If she answers yes. Ask some follow up questions to truly understand why she entered into the relationship.

6. How many relationships have you been in?

It can be very difficult to know if a woman is telling the truth about how many partners she’s had, so why bother asking, right? Why should you even care?

I’ll tell you why you should care: Studies show that a woman’s likelihood of infidelity is positively correlated with the number of people she’s slept with. So the more partners she’s had, the more likely she will cheat.

I don’t want to sound cynical, but that’s just the way things are. She may or may not be honest with you about her partner counts, but don’t let that stop you from doing what little you can to get a ballpark estimate… without being creepy about it, that is.

7. When did you lose your virginity? How did you lose your virginity?

You need to be very, very careful with this question. It isn’t one you can just ask willy nilly.

You might think it’s all fun and games, but you never know the can of worms it will open or even if you’re prepared for the answer. What if it turns out that she lost her virginity to a guy who raped her?

These types of questions to ask your girlfriend should be reserved for when the two of you are very close and open with each other.

8. Do you have any regrets from your past relationships?

People like to believe they live a life without regrets, but how can anyone really learn to do things differently if they’ve never felt bad about their decisions?

The truth is, many of us have regrets, and relationships are one area where even the smartest among us are bound to screw up. 

The lessons, if any, see learned from her past relationship mistakes will transfer over to your relationship, so it’s worth knowing.

9. What was your best day ever, and why?

When someone tells you about the best day of their life, you are essentially getting a  blueprint for who they are as a person.

Carefully listen to her answer to find out if the underscoring emotional experience of that day is something you vibe and connect with.

10. What was it like growing up in your family? Are you close with your siblings? What sort of rules did you have in your house growing up?

These open-ended questions to ask your girlfriend can help you learn about her family values and possibly her personal values without targeting specific individuals.

Knowing about her life growing up can give you a whole new perspective on who she is, especially when considering that many of our formative experiences shape our relationships.

11. When you were little, what did you want to be when you grow up? And do you still want it?

She was probably asked this a lot while she was growing up. Has her answer changed now that she’s older?

This is one of the most considerate questions to ask your girlfriend. It gives you an opportunity to find out what she wants so that you can help her achieve it.

11 Money Questions To Ask Your Girlfriend

Couple holding cash money to their face.
These questions to ask your girlfriend will help prevent or resolve relationship problems caused by money issues.

Ah money, the number one cause of fights in relationships. Did you know that around one third of millennial couples break up because of financial differences?

Money is not exactly the most exciting or sexy thing to talk about with your significant other, but it is a topic that must be addressed for the sake of your relationship.

Here are 10 money questions to ask your girlfriend to see if she’s on the same page as you are financially.

1. What would you say is the best thing about money: it provides security, it allows you to create good memories, or it allows you to buy nice things?

This question will reveal a lot about the kind of person she is and what she values in life, particularly if she is frugal with money, values experiences, or values objects. 

Like most guys, the last thing you want is to be shacked up with a girl who drains you of your hard-earned money. Instead, you want a girl who you can have wonderful, positively memorable  experiences with.

2. What are your financial goals?

This is an excellent money question to ask your girlfriend for when you’re thinking about taking the relationship to the next level. It will help you see if she has the financial mindset for a more serious relationship, possibly one involving children and a house.

But even if the two of you are not ready to talk about money, discussing your financial goals is a good way to gauge whether the relationship is heading in the right direction and expose current or future financial stress factors that need to be addressed.

Don’t just be dreamers; you must also be doers.

3. How good are you with budgeting money?

Not only is good money management a great skill for anyone to have, but relationships are often difficult if both couples are bad with money.

At least one of you should be good with money. If that’s not the case, now is the time for the two of you to take some classes, preferably together.

4. What drives your financial decisions?

It helps to have clear money guidelines to help you make smart financial decisions. 

Assuming she has some, this question should help you better understand why she makes the decisions she does.

5. What would you do with your life if you were suddenly awarded a billion dollars?

Although this is one of the least serious money questions to ask your girlfriend, it can reveal a lot about her priorities.

She could literally buy anything she wants with a billion dollars. However, pay close attention to the first things she chooses to spend her money on.

6. What do you think is worth spending extra on to get the best, and what do you think is a waste of money?

The first part of this question will give you a good idea of the type of things she’s likely to spend money on in the future (hope that they are useful things), while the second part should give you a heads-up on the things you probably shouldn’t buy, lest you want to upset her.

7. In a relationship, when should a man pay for something, when should a woman pay something, and when should they split the cost?

There used to be a time when the man in the relationship was required to handle all financial matters. While that might still be the case in some social circles, women have proudly assumed more financial responsibility.

This question will help the two of you lay down some expectations with regards to money, which should help avoid problems in the future.. 

8. Would you rather invest in a house, or invest in experiences, like traveling? 

A really good question to help determine her priorities in comparison to yours. You would be surprised at how many young people would rather spend their money on experiences rather than on a house.

9. Do your parents pay for any of your current bills? If they do, will they be continuing to help you in the future?

This should help you determine how well she’s able to carry her own weight. If she’s in financial straits but healthy enough to work, you would want any serious financial assistance from her parents to be temporary.

10. How much debt and savings do you have? At what age would you like to retire? What are our retirement goals?

This series of money questions to ask your girlfriend will serve you well if the two of you are planning to get married.

Marriage and even cohabitation are legal bindings in most parts of the world, especially when children are involved. You must define your finances in relation to her finances, and make sure your goals and values with regards to money are aligned.

11. How many kids do you want to have? 

Yet another money question to ask your girlfriend when the relationship is serious and you’re considering starting a family.

Did you know that the cost of raising a child is around $233,610 for a middle-income family? And that doesn’t even include the cost of college.

Raising children is difficult emotionally, physically, and financially, and shouldn’t be taken lightly. 

22 Random Fun Questions to Ask Your Girlfriend

Laughter is the key to a girl’s soul, so make her laugh with these funny questions to ask your girlfriend.

The science is in: Girls love funny guys. Few things turn them on faster than a good sense of humor.

Don’t consider yourself to be funny?  Don’t worry. All it really takes is a bit of light-hearted comedic banter to keep your conversations upbeat. 

The following are some of the best fun and funny questions to ask your girlfriend.

1. What phrases have guys used to try and conquer you with?

This is a very fun question to ask your girlfriend, and her response will probably make you laugh out loud.

It will also show her that you have a sense of humor. Because, you know, girls love funny guys.

2. If you could jump into a pool full of something, what would it be?

Her answer can be anything — a pool of candy, money, stuffed Baby Yoda dolls, just you name it.

This seemingly silly question can tell you a lot about the kind of person she might be. Is she down-to-earth, serious and goal-oriented, materialistic, etc.?

3. If you had a superpower, what would it be?

How could there be a list of funny questions to ask your girlfriend without mention of superpowers. Who doesn’t wish they had superpowers?

The answer to this silly question can vary from person to person. Maybe your girlfriend wants the power to read minds so she could hear what YOU are thinking about her, in which case I pray for her. 

Having access to a guy’s mind can traumatize a girl for life.

4. What is your destination for the trip of your dreams?

Many girls love to travel. If your girlfriend is one of them, brace yourself for an engaging conversation about the many wonderful and interesting places around the world.

Even if she isn’t a traveler at heart, there is likely one place she dreams of visiting. What is it?

In addition to helping you find out if your desires are similar, this question could make her think you want to travel with her somewhere, an idea girls tend to find tempting.

5. If you could live anywhere, where would it be?

Most people aspire to live somewhere they frequently visit, if at all. Maybe she has one or even several. 

Is it a place brimming with activity or one that’s relaxed and downtempo? Is it some far-flung location that no one has ever heard off?

As you can see, this question can tell you something about her personality and spark an engaging conversation that branches off into other topics.

6. What are your secret skills? What skills do you want to learn?

Girls love to talk about themselves, and your girlfriend is almost certainly not an exception. Here is her opportunity to brag about herself.

If you’ve been together for a while and think you know her very well, her answers might surprise and even shock you. 

Definitely one of the most peculiar questions to ask your girlfriend.

7. What is the most embarrassing thing that happened to you?

If there’s one thing as certain as death and taxes, it is that we will all make a complete and utter fool of yourself many, many times throughout the course of your life. I’m talking about those truly cringeworthy moments that still make you shake your head in disbelief.

Have her reveal the funniest incidents first if you don’t want to embarrass her, and then continue to more somber ones. I am sure the two of you will get a good laugh out of this question. 

8. What things would you grab if your house was on fire?

We all have material objects that we cherish and appreciate. This fun question to ask your girlfriend can reveal a lot about her life priorities.

She could pick anything really. It could be fun, wacky, or something novel and practical.

Instead judging her, find out why she picked those particular items.

9. If you got stuck in the elevator and was forced to listen to only one song, which would it be?

Taste in music can say a lot about a person. Did you know that people who are high on empathy tend to prefer mellow music that evokes deep emotion, while those who are more systematic prefer intense, more hard-hitting music?

This funny question to ask your girlfriend is a more interesting way of finding out what she likes than simply asking what her favorite band or artist is.

10. Do you prefer texting me so we can spam each other with emojis or call so we can hear each other laugh?

Definitely one of the most random and silly questions to ask your girlfriend. She won’t see it coming.

Use it as an ace card. If your girlfriend takes pleasure in talking to you and having silly conversations, then you and my friend are one lucky guy.

11. Since people from Poland are called Poles, why are people from Holland not called Holes?

A completely silly and random question to ask your girlfriend, let alone anyone. But, sometimes, the silliest questions lead to the biggest laughs.

Try this one on her and see how it transforms the conversation.

12. Would you rather be trapped in a dark small box or at a Justin Bieber concert with no doors or windows?

Justin Bieber gets a lot of hate, and probably for good reasons. It may have to do with his music, his personality, the way he looks, or a combination of the three.

What could possibly make her want to choose a dark, claustrophobic box over this Canadian?

13. Have you ever been in a cat fight?

Every girl has been in at least one or two cat fights in her life, so your girlfriend is probably lying if she says she hasn’t.

It will be fun listening and laughing together as she spills the beans.

14. Ask the girl you like: Can you spell “supercalifragilisticexpialidocious” or say “Quizzical quiz; kiss me quick?”

Certainly one of the most, if not the most, random questions to ask your girlfriend. After wiping the “WTF?” reaction off her face and untangling her twisted tongue, she might punch you for pulling such a fast one.

Feel free to make up any silly, hard-to-spell word or string together any tongue-twisting phrase you want. You will both laugh, that’s for sure.

15. What is one funny thing that somebody has walked in on you doing?

This is a super funny question to ask your girlfriend for obvious reasons. 

Perhaps it was when someone walked in when she was talking to herself in the mirror, or when she was busting some crazy dance moves. Heck, you might even have been involved in the incident!

Whatever it was, the two of you will certainly get a laugh out of it.

16. What’s the most funny prank you’ve ever pulled on someone?

All of us have pulled a prank or two on someone before, but some people were just born to prank.

Is your girlfriend a born prankster? Should you be on your guard for shenanigans?

This fun question should result in an upbeat conversation.

17. Why do girls usually push the door when it says pull?

It sounds like a silly question, but this strange behaviour is a mystery that even girls don’t understand.

I’m sure there is a scientific basis for it, but see what funny explanation she can come up with.

18. Me, a rabbit, and a panda: cuddle one, hug one, kiss one?

One of the cheekiest questions to ask your girlfriend, that’s for sure, and certainly one that will make her laugh.

It will be fun and interesting to see what she chooses. And judging by her options, you win no matter what.

19. If I offered to do something really funny for you, what would you ask me to do?

This one will put you in the limelight in a big way, so be prepared. You will be at the mercy of her imagination… a woman’s imagination. 

She can literally ask you to do anything, from the mundane to the downright weird. Just don’t be surprised to find yourself walking around in public wearing lipstick, high heels, or both.

20. If you could be a man for just one day, what would you do?

Few questions to ask your girlfriend have the potential to be as fun as this one.

Every girl has wondered what it would be like to be a guy, so this is her opportunity to share what she thinks guys do. 

Even if her answer ends up being wrong on so many levels, you will both find levity in poking fun at guys.

21. Don’t you think it’s a crime for you to be so beautiful? Don’t you think you need a handsome guy like me?

This is a shamelessly corny question to ask your girlfriend, and that is precisely why it will likely put a smile on her face.

Just don’t be too serious when asking it, OK? The last thing you want is for her to think you are vain.

22. What would you do if you could be invisible for one day?

Like any normal person, she could probably think of 100 different things she would do. 

Would she play a prank on some she knows? Take a nap at work? Sneak into a men’s locker room?

You are bound to get some interesting answers, along with some good laughs.

20 Deep Questions to Ask Your Girlfriend

Young couple about to kiss.
Generally speaking, the deeper the questions you ask your girlfriend, the deeper the conversation.

How well do you know your girlfriend? I mean, really know them?

Whether or not you know her well, the truth is that we can all get to know our significant other a little better. 

Fortunately, there’s a fairly easy way to do that, and it can be a lot of fun. You just have to spark a good conversation by asking the right questions.

These engaging deep questions to ask your girlfriend will help you connect with her on a more intimate level.

1. What kind of person do you envision yourself as, and how do you want people to remember you?

Most people are too focused on the hustle and bustle of life to give this question much thought, so you might have to give her time to answer it.

It should give you a good idea of what qualities she hopes to develop.

2. Who’s the closest person to you in your extended family?

If you want a second opinion on your girlfriend, this person is probably someone you should definitely get to know.

Be sure to ask her why he or she is so special.

3. At what age do you feel like you become an adult?

One of the deepest questions to ask your girlfriend, because even science doesn’t have a clear cut answer for when a person becomes an adult.

Age alone does not make an adult. With each milestone, comes a host of new responsibilities and the opportunity for transformation. 

Which milestone does she think turns boys and girls into men and women?

4. What single word do you think really, truly describes who you are as a person?

The one word that your girlfriend believes defines her might not be the same as yours. When she tells you what she thinks her greatest characteristic is, find out why she thinks that and show her your support.

5. Would you be willing to lie to a court for a close friend if it meant saving your friend from going to jail?

Some people would put their reputation and self-respect on the line to protect the image of those they love, but you might be surprised at how many people would answer “No” to this question.

It should give you an idea of how strongly your girlfriend’s ethics influences her decision.

6. If you had to pick how you died, what would it be?

We debated whether to include this one in our list of deep questions to ask your girlfriend or in the funny questions section, and that’s because her answer can go either way: hilarious or sentimental.

A blaze of glory? Suffocated by a hundred kittens? Or perhaps surrounded by loved ones? 

Jokes aside, how your girlfriend wants to go out can tell you a lot about how she wants to live.

7. What would you do tomorrow, if you lost your job and money and we had to start over?

What are the things, people or memories that she is stubbornly holding onto? Has she been pursuing the wrong career?

Asking this question will help you get the necessary answers. Just remember to be supportive of her.

8. If you could choose the sex of your child, would you?

Beyond finding out what gender she wants her children to be, and why, this question let’s her share her thoughts on life and science.

In particular, does she think having the option to choose upsets a natural process in society and nature?

9. Would you ever design your children if given the option, and what features would you give them?

If she could design the perfect child, would she, and what would the child look and behave like?

One of the most controversial and deep questions to ask your girlfriend, one that can develop into a very long conversation. 

You’ve seen what humans have done with dogs and other animals. Does she have any ethical hiccups about the concept, especially when human beings are the test subjects?

10. What challenging experiences have made you stronger?

It’s often the most painful experiences that lead to our greatest personal, emotional, spiritual and even financial growth.

You want to be with someone who knows a thing or two about hard times, because such a person can help you grow through your difficult times.

11. What would you wish to accomplish in life, if you could only accomplish one major thing?

Learn about her passion, and see what you can do to help her achieve it. 

Show her that you want to be part of her dream.

12. When was the last time you failed really badly?

This job interview-like question is great for your still getting to know your girlfriend. 

Her answer, particularly what she learned from the experience, can tell you a lot about her resolve and how well she holds herself accountable for her life actions.

13. If we could live in a virtual world, but we could never come back to this one, would you want to?

Advancements in virtual reality technology makes this a very good, thought-provoking question to ask your girlfriend. 

Everyone wants to live in their own world. Assuming she’s not one of those people who thinks real life is actually a virtual reality, would she want to leave her existing reality for another one? 

You will definitely learn about the aspects of her human life she wants to escape in the lengthy conversation that ensues.

14. Do you believe evil people are born evil?

The world is full of some truly dangerous people, but were they born that way or did their environment mold them into the monsters they are? One of the deepest questions to ask your girlfriend, indeed.

You can make the conversation even more engaging by asking her if humans in general are born good or evil.

15. Is life anything like you had pictured it would be growing up?

Not only will this question help you find out if your girlfriend is living the life she imagined, and whether someone like you is supposed to be in it, but it will also give you an idea of how much she has changed / grown over the decades.

16. Do you believe everything happens for a reason?

Call it nature, call it god. We have all wondered if there is some force behind our lives.

Does she believe people face difficulties in order to learn to let go, things go wrong so that we appreciate them when they’re right, and that good things fall apart so that better things can fall together? 

Get to know her philosophical and spiritual side.

17. What belief do you have that most people disagree with?

Sometimes you just have to agree to disagree. Get to know her viewpoint on certain aspects of life, and see if you can back her up as she fights her corner by trying to see both sides of the picture.

18. Are you holding onto something that you need to let go of?

One of the hardest lessons in life is letting go of the things that don’t serve us, be it anger, guilt, love, or loss. But it’s often when we let go that we grow the most.

Having her talk about the unproductive thing she’s holding onto could be the catalyst for her finally letting go.

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

Life can throw at us some truly painful experiences, but it’s what we learn from them that matters the most.

Let your girlfriend share her wisdom. Find out how much of a better person she’s become because of the difficult lesson.

20. What first attracted you to me? How has that one attraction changed since then?

One of the few questions to ask your girlfriend that’s actually about you. I’m sure you will be intrigued to know how her physical and emotional attraction to you has evolved over time.

Use the knowledge obtained to improve yourself in a way that makes her more attracted to you.

How To Ask Your Girlfriend Good Questions

Having a repertoire of good questions to ask your girlfriend is one thing, knowing how to effectively use them is another.

The goal is to have conversations that strengthen your relationship, and this requires the two of you to be open with each other with regards to your passions, fears, needs and wants.

Follow these three tips to have meaningful conversations with your girlfriend.

1. Start By Sharing

To have a good conversation, you will need to get out of yourself and make it about the other person.

Show your girlfriend that you’re more than just a charming lump of flesh and bones by openly sharing your passions, interests and hobbies with her.

Don’t be afraid to show excitement when doing so, and encourage her to do the same!

2. Practice Active-Listen

Women like to believe that men don’t listen. Prove them wrong!

When having a conversation, most people are usually focused on what they want to say next while someone else is speaking. In other words, they are not properly listening to what’s being said.

Now that you know, stop and try to force yourself to listen whenever you find your mind rushing to a response 

Show your girlfriend that you do listen to her by recalling your past conversations.

3. Be Curious

To keep a conversation engaging, take advantage of active-listening and ask follow up questions. 

Go deeper and deeper until it is necessary to move onto an entirely different question or subject.

Generally speaking, the deeper the initial question, the more engaging the conversation.

Questions To Ask Your Girlfriend – Use Them

So there you have it — over 100 good questions to ask your girlfriend, plus tips on how to have an engaging conversation.

Be curious and show interest by actively-listening and posing good follow-up questions, but don’t make her feel like she’s being interviewed. Respect her privacy and try not to take it personally if she doesn’t want to answer a question.

The secret sauce of having a great conversation is asking the right question at the right time. Not all the questions we provided are appropriate to be asked any time, so try to get to know her first before using any of them.

This is the most detailed list of questions to ask your girlfriend, so share the knowledge with your friends, family or anyone you think needs it.

You can find more content like it from here.

Written By

Kwame Owusu is a personal development coach and the founder of Too Manly. He holds an MBA from a top business school and is committed to helping men all around the world look, feel and live the prime of their life.



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