Best Questions to Ask Your Girlfriend

Best Questions to Ask Your Girlfriend

Not all women are prone to opening up about themselves or their emotions. When one of them becomes your girlfriend, there is a higher level of opening up that must happen for the relationship to survive and be healthy. 

That is the intent behind the following sets of questions. You may find that some questions cause disagreement, which certainly doesn’t mean you should end the relationship, but you may want to decide how important they are to you in a partner later on. I encourage you to have an open mind about asking follow-up questions to dig deeper.

As she answers, be aware of how she feels towards the question you are asking. Maybe she needs to be with you for longer to open up about some of the things these questions pry into. Gauge her mood and her answers to guide you with these questions. We have provided you with several categories to choose from, depending on what you really want to know about your lady and what you feel she is willing to share.

Best Questions to Ask Your Girlfriend

Feel free to begin at the first question, or use her answers to guide you to different topics available here. You can click on the links below to jump to other topics if you feel the topic you are on is done or too sensitive for her. I hope you enjoy the experience of becoming closer to your girlfriend as you share the conversations this list will inevitably spark.

General | Future | Money | Past



 1. Where do you feel like you can most be yourself?

These are the kinds of questions that make for a healthy relationship.

2. If you could change one thing about yourself, what would it be, and why?

If you can be honest about these kinds of things, your relationship will be that much stronger.

3. If you could go anywhere in the world, where would you want to go?

Maybe you can travel there together someday.

4. What decade from the past do you feel that you most belong in?

We all feel that we’ve been born in the wrong era.

5. Who is the one person in this world that knows you best?

We all have that one person that we’re closer to than anyone.

6. If you had one day left to live, how would you spend it?

Get to some deeper levels with her, and your relationship can only get stronger.

7. What’s your favorite quality in your best friend?

They say opposites attract, so maybe they’re thriving where you lack and vice versa.

8. What fictional character do you identify with most?

Would you be one of the classic tropes, like a Romeo or a Juliet? Or would you level more with a modern character, like a Mike or Eleven?

9. Would you say that you readily accept compliments?

Sometimes, it takes a little bit of humility to recognize how great you are.

10. Do you believe in love at first sight?

A little romance never hurt anybody.

11. Are you a pessimist or an optimist?

A lot of people consider themselves to be a little bit of both.

12. Do you believe everyone has a soulmate?

The universe is a pretty strange place, but is it working in our favor?

13. What are the three best things a boyfriend can do for you?

Be ready to take good notes!

14. What is something crazy you have done in the past month?

How much of a dare-devil is she?

15. How much of an outdoor person are you?

A good question to know if she likes to hike and you don’t, or maybe you like to hike, and she doesn’t. Maybe you two could compromise and find other awesome things to do.

16. If your house caught on fire, what three items would you first grab?

You can be able to tell what is important to her in life.

17. Would you tell a stranger if they had something in their teeth? Toilet paper stuck to their shoe? Dress tucked into their underwear, etc.?

These are the character-defining moments that can make or break us.

18. What law would you be most likely to break?

Criminality is a character trait.

19. Tell me your favorite joke.

Not a question, but still appropriate.

20. Are you a dog or a cat person?

This is an essential question if you’re planning on having a future together.

21. What’s your guilty pleasure?

We all have that one TV show/movie/book that we blush about.

22. How do you deal with conflict?

This is important to know because you are sure to have some disagreements in the relationship.

23. What are your three favorite movies?

It’s nice to know what movies she likes so you can watch movies together. 

24. What is something you like to do for a Friday date night?

Maybe she really likes to get desserts, or she likes to go dancing, all good things to know.

25. What’s the most interesting autobiography you’ve ever read?

There are so many interesting people in this world.



1. How do you think you’re going to spend the last few years of your life?

This is somewhat of a scary question to think about, but it’s worth thinking about.

2. Take a minute and think about your perfect life. What does it look like?

A good question to ask because you two may have different goals in life. She might want to travel and be an influencer, and you just may want to stay put and work a 9-5 job.

3. What is something adventurous you would like to do?

Skydiving? White water rafting? Ice climbing?

4. If you knew when you were going to die, what would you like your last meal to be?

There is the saying live like you’re dying, right? 

5. Do you have some goals you are working on?

If she is comfortable sharing some, maybe you could help her.

6. After a long day at work, what do you look forward to?

It is nice to know how she unwinds.

7. If you could ask three questions about your future, what would they be?

This can help you see her hopes and dreams.

8. Do you have an idea of how you want your dream home to look? 

A good way to get some ideas for your future dream home.

9. How do you think the next ten years of your life will look?

This general question can tell you a lot about your girlfriend that you don’t already know.

10. What are a few things about the future that scare you?

We all have a few things that make us nervous about the future.

11. Do you think the future will be better than the present or worse?

All we can do is hope for the best.

12. At the end of your life, what do you want to be your greatest accomplishment to be?

Write a book? Raise children? Run for governor? 

13. Have you ever been to a fortune-teller?

A fun question to find out what could be in her future, if you believe in that stuff.

14. Do you think humans will evolve just like all other animals, or are we destined to go extinct?

Deep questions require deep answers.

15. What are some small changes that can be made that would improve the lives of a country’s citizens?

Politics are always a pretty relevant conversation topic.

16. What kinds of roadblocks do you think you’ll have to face in achieving your dreams?

No one said life was going to be easy, but when you’re going after your dreams, it’s bound to be worth it.

17. What do you think you will look like when you’re old and grey?

Will your eyes still sparkle? Will your smile still shine?

18. Do you think you will ever feel fully satisfied with life, or is there no way you will ever stop wanting more out of life?

Ambitions are all fine and good, but it’s okay to be content at some point.

19. Would you ever consider running a marathon, doing a triathlon, etc.?

Mind over matter is sometimes the best way to accomplish things in life.

20. Do you consider yourself to have unlimited potential?

Sometimes our own self-deprecation is the only thing holding us back.

21. As you grow older, what kind of message do you hope to give to those younger than you?

We each have our own lives to lead and legacies to leave.

22. Do you think emotional goals are just as important as temporal/material goals?

In our modern age, it’s easy to sacrifice happiness for success, but what is success without happiness?

23. Do you think it’s smarter to follow in the footsteps of the greats or carve your unique path to success?

No one is saying either one is easier than the other.

24. Do you have a bucket list? If so, what are some of the items?

If she doesn’t have one started, this would be a great list to start making.

25. Do you have a future trip/vacation planned?

Maybe you could join her.



1. Are you the type of person that manages a budget, or do you spend money pretty freely?

Every relationship should be based on trust and open communication, especially about finances.

 2. On a scale of one to ten, how important is money to you?

This is an essential question to ask.

3. Does money equal success? Power? Safety? Define it in your own words.

It’s important to discuss how you both view money individually.

4. What would you do with $5 million?

There are a billion and one things you could do with money like this.

5. What was the last thing you bought? Was it worth it?

Sometimes it’s important to point out each other’s flawed decision-making skills. Think of it as constructive criticism.

6. How often do you go out to eat?

Surprisingly, this could be the thing that breaks your bank.

7. What are your financial goals?

It’s easy to make the tough financial decisions when you’ve both got your priorities written down and in order.

8. What’s something you splurge on?

Big purchases are sometimes necessary… sometimes.

9. Would you rather spend a lot of money on an experience or an object?

Does happiness lie in material things or all the memories made?

10. Did you get an allowance as a kid?

How much did your parents give them, and how has that impacted their views towards money as an adult?

11. Do you think your parents were good with money?

We often take after the habits of our parents, so this is an important question.

12. Would you consider, or have you ever budgeted?

This might seem like an uncomfortable topic

13. Are there things you think are worth spending extra money on to get the best? 

This can let you know what she values, as well as how much money to possibly set aside to get her those items.

14. What do you think is a waste of money?

We’ve all wasted money on something.

15. What scares you about money?

Not having enough of it would probably be a big concern.

16. Did you grow up with a lot of money, or did you live a relatively poor lifestyle?

Did you or your parents pull yourselves up by your bootstraps, or did you inherit everything you’ve gotten?

17. What is your opinion on debt?

Are student loans acceptable?

18. Are you more prone to saving or spending your paychecks?

Some of us are savers, and some of us are spenders.

19. What do you enjoy about money?

Money can provide security, create good memories, or just allow you to eat very yummy food.

20. When do you think a couple should split the cost of buying things?

Will he be paying for everything? Will you be paying for some items? Would you two split the cost?

21. If money wasn’t an issue, what job would you like to have?

Movie theater usher? Farmer? DJ?

22. What is a charity you would like or do give to?

This shows what is important to her.

23. If you found the perfect gift for someone, but it was costly, would you buy it?

Is it the thought that counts? Or the actual gift?

24. If you won the lottery, what is the first thing you would buy?

A fun question to think about.

25. If money was not an issue, where would you like to live?

Would she like to live in a big city? Or a nice quiet country spot?



1. What’s one thing that has happened to you that has made you a stronger person?

Your girlfriend is sure to be a much tougher girl than she lets on. Don’t be scared to ask the hard questions.

2. What’s one thing that happened to you that made you feel weak?

In a relationship, it’s important to be vulnerable, open, and honest with one another.

3. Who do you think has had the most significant influence on the person you are today?

There’s quite a lot to this question.

4. When you were younger, what did you want to be when you grew up?

We can’t all grow up to be astronauts and monkey trainers, but that doesn’t mean it isn’t fun to think about.

5. What did you like/dislike about the guy you were dating in the most serious relationship you had?

This is an excellent question to ask to see what kind of guys she is into.

6. Have you cheated on a guy before?

This is very important to know, but you also have to ask the right way and the right time. 

7. How often would you and your ex go on a date?

A good question to see how much time she spent with her ex-boyfriends. 

8. What was the last thing that made you laugh?

Hopefully, it was you.

9. What was the last thing that made you cry?

Everyone handles emotions differently. Figure out how she does.

10. What is your favorite memory from childhood?

Knowing about each other’s pasts can open the doors to your future.

11. When was the last time you were genuinely embarrassed?

Not the cute, surprise-party, Instagram-friendly type of embarrassed. More like the “I-farted-really-loudly-in-a-super-important-work-meeting” type of embarrassed.

12. If you could describe your middle school experience in one word, what would that word be?

We were all a little cringey back in those days.

13. If you could change one thing about the way you were raised, what would it be?

How different would your life be if only one thing were different?

14. Who was your best friend when you were a kid?

Reminiscing on childhood memories is a great way to pass the time.

15. Did you ever have an imaginary friend?

We all had one at some point.

16. How did you spend your summer breaks as a kid?

Sunny days, no homework, and LOTS of time outside.

17. What was your favorite family vacation?

Was it that long-winded road trip where the car broke down, and you got lost in the middle of Kansas or the cruise to the Bahamas you took with all of your siblings?

18. What was the best birthday you ever had?

Sometimes the most memorable birthdays are the best ones.

19. What’s something that you chickened out of once, but now think you’d be brave enough to try again?

Riding that roller coaster? Maybe trying that weird-smelling ethnic cuisine you passed up a long time ago?

20. If you could write a letter to your younger self, what would you want to say?

This is a pretty deep question.

21. What was a terrifying movie or TV show you watched as a kid that you would not be afraid of as an adult?

Maybe you two could watch it together.

22. What one minute would you erase from your life?

Maybe it was something really embarrassing or really sad.

23. Did you like to play more outside or inside as a kid?

Maybe she still likes to play outside, or maybe her interests have changed.

24. What is the craziest lie you have heard someone tell?

Yes, this also includes politicians.

25. What slang makes you feel old?

Maybe some of the slang she says makes you feel old.