60 Interesting Questions to Ask a Girl You Like


When you like a girl, it’s only natural to want to know more about her. However, it’s really not fun for her to answer questions about her favorite foods and favorite color. You want to make sure to ask her interesting questions that will also keep her entertained while giving you all the information you need to know about her.

It also helps to ask interesting questions in order to show her that you like her for more than just what’s on the surface. If you really want to keep a girl interested and get to know her way better, these are the questions you should be asking in order to make that happen.


  1. “Have you ever sat by the phone all night waiting for someone to call?”

This can show you just how much she values those that are important in her life.

  1. “Do you believe that he will always have a special place in your heart?”

This is in reference to any of her previous boyfriends. It’s not an awkward question to ask by any means and you can learn how open and honest she is about her past.

  1. “Do you believe that everything happens for a reason?”

This is a powerful question that can tell you more than you need to know about her.

  1. “Have you ever had a crush on a friend’s parent?”

This will probably make her laugh, but it’s also very interesting to know about her.

  1. “Do you rather follow your heart or your head? Why?”

This will show you if she’s a logical thinker or someone that relies more on her feelings.

  1. “Do you prefer to share finances with your partner, or keep them separate?”

Not only is this a standard question to ask if you’re in a serious relationship, but if you ask this early on you can tell what she values in a serious relationship and how separate she sees a successful relationship.

  1. “Do you sleep with a stuffed toy? What is it?”

Many people rely on objects for comfort, find out if she’s one of them with this question.

  1. “Describe the appearance of the person you would like to date?”

This may be an obvious question to see if you’re a fit, but it can also tell you how much stock she puts into how someone looks versus what their personality is like.

  1. “Have you ever hated loving someone?”

This is a deep question that will reveal a lot about her.

  1. “Do you snore or steal the covers or roll around in your sleep?”

She may not like answering this question, but it’ll tell you a lot about her sleeping habits.

  1. “What is something you have tried, but will never do again?”

Asking this can reveal her biggest regrets and mistakes.

  1. “What quirky habit do you have?”

Everyone has one! Finding out hers can let you know about other habits she may have but doesn’t want to share.

  1. “Who is your best friend?”

This is always an important question to ask just so you know who is closest to her and who knows the most about her.

  1. “What is the one thing you did in your past you wish you could undo?”

Find out more of her regrets with this question and learn about what she’s learned from her past.

  1. “What is your biggest fear?”

This can be as small as a spider or as big as dying too young. Learning her fears can teach you a lot about who she is.

  1. “What is the one place in the world you wish you lived in?”

Asking this will show you just how much she enjoys her current life and how big her aspirations are.

  1. “Would you rather be loved or have a lot of money?”

Find out what she values the most by asking this important and interesting question.

  1. “What is the happiest memory from your childhood?”

With this question, you’ll learn just how happy or miserable her childhood was. This can tell you a lot about the person she is now.

  1. “What is the most embarrassing moment of your life?”

Everyone has an embarrassing moment! Make her share what hers is and you’ll be able to know what she’s uncomfortable with.

  1. “What would your dream date be like?”

Everyone has a vision of what they’d most like on a date. This can give you ideas if you get the opportunity to take her on a date.

  1. “What would you change about your personality & look?”

Some people wouldn’t change a thing. This can tell you what her confidence level is and how much you would have to boost her up in a relationship.

  1. “Who has influenced you the most in your life?”

This can tell you more than you would ever need to know about who she is on the inside.

  1. “What is something you used to do as a child that you wish you could still do?”

I know mine would be to nap every single day. This will help you find out what she loved most as a child.

  1. “What is the worst thing about dating?”

Asking this question can help you avoid making a mistake if you ever want to date her.

  1. “What is the one career you would love to enter?”

Not everyone can pursue their dream job. Finding out what hers is can help you learn more about what her greatest interests are.

  1. “Are you close with your family?”

If you ask this question, be prepared to learn about some issues she may have regarding her family. This can also show you why she acts a certain way.

  1. “What is the one movie that influenced your life the most?”

Movies can have a powerful impact on a person and finding out the one that did it for her can show you who she really is beneath the surface.

  1. “Where is the one place in the world you feel safe?”

If you want to know her better than anyone else, ask this question.

  1. “What is the one thing you want to experience before you die?”

Everyone has something they want to do before they kick the bucket and it’s a great way to learn what’s the most important to her.


  1. “What is your ultimate goal in life?”

This can tell you what is most important to her and in what subject she will never change her mind.

  1. “What kind of things really makes you laugh?”

This is not only good for you to know to make her laugh, but you can find out her sense of humor with this question.

  1. “What is the most silly pick-up line or a phrase guys used on you to win your attention?”

If you want to make her laugh and find out what not to do, ask this question.

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

This is a funny question that can lighten the conversation but give you serious answers at the same time.

  1. “If you had to make out with a friend of the same sex to save the world from aliens, whom would you pick?”

Find out which of her friends she wouldn’t feel awkward kissing!

  1. “What was the funniest moment in your life?”

This may be something embarrassing for her or it may be something really funny that the two of you can laugh at. Either way, it’s great to know what she finds humor in.

  1. “Have you ever had a crush on an animated character?”

I think we’ve all liked an animated character. This is a great way to find out which shows she liked and just to make her laugh.

  1. “If the world froze for an afternoon and only you could move and no one could see you or remember what you did, what would you do?”

This will help you understand what she’s embarrassed to do or what she think she’ll be judged for.

  1. “Which habit are you proudest of breaking?”

There has to be something that she used to do that was harmful that she is happy to be rid of. Finding out what can help you learn more about her.

  1. “If you had to pick an animal, which animal do you find the sexiest of all?”

This is a really funny question that she might think is silly, but it’s great to lighten the mood and get her view on an adorable animal.

  1. “What word starts with a letter “f” and ends with letters “u-c-k”? (The answer is “firetruck” so maybe you should save this questions until you know each other better)”

This is a really funny trick question that she may get or she may use the word that most people do. It’ll show you just how much she thinks about a question before answering.

  1. “How is your relationship with your mom?”

If it’s bad, you may learn something valuable about her. If it’s good, then you know she must value family more than other things.

  1. “Do you have any brothers or sisters?”

This is an obvious question to ask because siblings influence your life in a lot of different ways.

  1. “What do you value the most when it comes to friendship?”

This is a very straightforward question that will tell you so much about what’s important to her in the people she surrounds herself with.

  1. “How is your relationship with your father?”

Girls who are closer to their dads tend to be tougher and more independent than those who aren’t. So asking this question can tell you a lot.

  1. “How often do you talk with your parents?”

Again, this will tell you a lot about her values in family.

  1. “What’s your best memory with your father/mother/sibling?”

Not only is it fun to hear stories about her family, but she’ll be happy to tell them and you can learn about her family through this.

  1. “What jobs did your grandparents do?”

Grandparents tend to have a big influence on their grandchildren’s careers and by asking this, you’ll see just how much they do.

  1. “Who do you think knows you the best?”

If you want to know who you should be talking to about her, ask her this question and find out.

  1. “Where is your bloodline originally from?”

This is just an interesting question to ask to see where her family originated and if it’s similar to your own ancestry.

  1. “How regularly do you see your best friends?”

This will help you understand the type of person she is. Some only need to see their friends occasionally while others are dependent on them for entertainment and support.

  1. “What’s your favorite place in the entire world?”

If you find this out, you can go there and get a better sense of the things she likes and the environment she’s most comfortable in.

  1. “Where did you go to school?”

If you meet outside of school or later in life, asking her this can start up a really interesting and informative conversation. This can tell you if she likes to be closer to family, if she’s independent, or even her intelligence level.

  1. “What do you do, and how long have you been doing it?”

This is a career question that can tell you a lot about how much she likes her job or even how indecisive she is. Someone who has skipped around a lot for work tend to be more impulsive than others.

  1. “What were you like as a kid?”

What someone was like as a child has an awful lot to do with why they are the way they are. Asking her this can tell you about the deeper parts of her personality that you can’t see on the surface.

  1. “What’s on your bucket list?”

Finding out what’s the very most important thing to her can tell you a lot from a very little.

  1. “What type of music are you into?”

Music compatibility is really important in a relationship and the more alike you are with music, the better you’ll get along.

  1. “Do you have any nicknames? What’s the story behind them?”

This can be really embarrassing and a really fun conversation to have.

  1. “Are you a cat person or a dog person?”

Some believe the difference can tell you a lot about someone. Ask her and decide for yourself.

  1. “Did you like this place?”

Asking this during a date can give you hints as to what else you should do on the dates you have going forward.

  1. “Want to get coffee/dessert after this somewhere else?”

This is a great question to ask at the end of a dinner date to see if she’s into you or if she’s really not feeling it. Plus, you get to learn what dessert she likes or if she’s even into coffee.


Girls like complex questions that make them think. Not only will these questions reveal a lot about her, but she’ll see that you really want to get to know the real her – and she’ll love that.

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