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21 Questions to Ask a Girl You Like

Ditch the boring questions and small talk. Here are the essential questions to ask women to increase your attractiveness and make you more interesting

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Think about this.

If you could name one thing that every talk show host has in common, what would it be?

If you said “an outgoing personality”, you’re right, but it’s not what we’re getting at.

It’s that they all use question cards (also known as “prompter” cards).

No matter how outgoing or experienced you are at meeting new people, everyone runs out of topics to talk about from time to time.

That’s why having a list of backup questions (and removing “the filter“) is so important.

The same applies when you’re speaking with a girl you’re interested in.

Having a unique set of questions in your conversational arsenal will CATAPULT your attractiveness in the eyes of every girl you engage with.


Because the girl will INSTANTLY consider you to be a whole lot more interesting than every “so, do you come here often?” or “gee, how’s this weather?” guy (and there are a lot of them, trust us).

Asking good questions will make you more interesting.

Girls are attracted to interesting guys.

Romance, listening skills, and humor are all highly attractive qualities to women, and these traits can all be conveyed with questions.

But remember guys:

You also want to mix in a healthy dose of statements and stories so that you’re sharing your own experiences as well.

You don’t want the conversation to come across like an interview because that would be unnatural and awkward.

To help you along today, we’ve put together the essential list of good questions to ask a girl.

We’re confident that even if you can simply memorize a handful of these and apply them to your daily conversations, you will see a massive improvement in the quality of your interactions with women.

Post Contents

If you do not know how to ask the right question, you discover nothing. – W. Edwards Deming

Top 21 Questions to Ask a Girl You Like

If you’re going to memorize one list of questions, make it this one.

These are our tried and tested, top 21 questions to ask a girl.

1. What are you passionate about right now?

2. What do you look for in a guy?

3. What makes you happy?

4. Who are you closest to in your family and why?

5. If you could go back five years, what would you change about your future?

6. What’s your favorite time of year and why?

7. What was the best thing about where you grew up?

8. What would you do tomorrow if it were your last day on Earth?

9. What do you like most about yourself?

10. What’s your biggest dealbreaker in a relationship?

11. What’s your favorite movie of all time?

12. What’s been your proudest moment?

13. If you could do anything for a job tomorrow (with no obstacles in your way) what would you do?

14. Do you have any secret talents?

15. Is there something that you used to do that you loved, but you’ve now stopped doing?

16. What were you like as a kid?

17. What’s the most valuable thing in your life?

18. What’s your idea of a perfect date?

19. What’s the best advice you’ve ever received?

20. If you could live anywhere in the world, where would it be?

21. How do you think your closest friends would describe you?

100+ Good Questions to Ask a Girl

Hungry for more questions?

You got it.

Keep reading for 100+ more of the best questions to ask a girl, divided into categories for each different type of question.

Interesting Questions to Ask a Girl

Scientific studies have proven that fluid conversations create feelings of self-esteem, social validation, and belonging.

Interesting questions are a great way to create fluid conversations because they allow you to learn more about her perspective or personality. Through this, they invite further discussion.

By their very nature, that’s what makes them interesting!

Here are our go-to interesting questions to ask a girl.

  1. What’s the craziest or most out-of-character thing you’ve ever done?
  2. What’s your favorite thing about this city?
  3. What is your biggest “pet peeve”?
  4. If you could relive one day from the past, which would it be and why?
  5. If you could have any talent in the world, what would it be?
  6. If could choose only one long-term goal, either to own a house or to travel the world, which would you chose?
  7. What’s your favorite thing to do when you’re all alone?
  8. What’s your go-to karaoke song?
  9. What’s your idea of a perfect weekend?
  10. If you could take one book, one piece of clothing, and one food item to a desert island, what would they be?
  11. What’s on the top of your bucket list right now?
  12. What’s the last thing that had you so excited you couldn’t sleep?
  13. What would be your ‘Miss America’ platform?
  14. If you could invite ANY three people from history over for a dinner party, who would you invite and why?
  15. What’s the most spontaneous thing you’ve ever done?
  16. At what age do you think a person needs to “grow up? and why”
  17. Where is the next place you would love to travel to?
  18. If you could tell you of ten years ago one thing, what would it be?
  19. What’s something that you’ve never done but always wanted to?
  20. What’s the best gift you’ve ever received?

If you think you might not be an interesting guy, give this a watch:

Deep Questions to Ask a Girl

Deep questions are personal. They build trust and make a girl feel closer to you.

Here are our favorite deep/personal questions to ask a girl.

  1. What are the three principles you would want to pass along to your children?
  2. Would you describe yourself as a spiritual person? And if so, how does it shape your life?
  3. What’s been your biggest mistake and what did you learn?
  4. Who’s been the biggest influence on your life and decisions?
  5. What motivates you the most?
  6. When you were little, what did you want to do when you “grow up”?
  7. If you could change one thing about your personality, what would it be?
  8. What gives you the most adrenaline?
  9. What’s a common thing that you think about when you’re alone?
  10. Would you like to have kids at some point in your life?
  11. How often do you see your good friends?
  12. If you could be a fly on any wall, which would it be and why?
  13. How important is family to you?
  14. What’s your worst habit?
  15. What kind of parent would you like to be?

The rise of technology and human interconnectedness has given rise to a growing sense of disconnection emotionally, particularly when it comes to building relationships.

Despite these technological advances, one thing remains true. To build a strong relationship, there needs to be a meaningful connection.

Learn more about creating meaningful relationships in the age of technology in the below video:

Questions to Ask a Girl to Get to Know Her

Here are some excellent questions to ask a girl to get to know her. They’re a touch lighter than our deep and personal questions listed above.

  1. Where did you grow up?
  2. What did you study in college and why?
  3. What’s your favorite place to run away to?
  4. What do you do to cheer yourself up?
  5. How do you like to receive love?
  6. Who knows you best?
  7. What are you most attracted to in a guy?
  8. What subject would you like to learn more about?
  9. What makes you laugh more than anything?
  10. If you could ask me anything, what would it be?
  11. What’s your favorite type of food?
  12. Are you a morning or night person?
  13. What does it take for someone to become good friends with you?
  14. What kind of movies / TV shows do you like?
  15. Would you say you’re more introverted or extroverted?

Craving more ‘get to know her’ questions? Check this video out:

Flirty Questions to Ask a Girl

Confident guys show romantic interest by flirting. And, surprise:

Girls love confidence.

Flirting also has several health benefits including boosting your immune system, relieving stress, and reducing symptoms of loneliness.

Here are a few of our go-to questions for getting your flirt on.

  1. What do you like to do the most when you’re alone?
  2. When’s the last time you got butterflies and why?
  3. What’s your opinion on manscaping?
  4. Who’s your biggest celebrity crush?
  5. What’s your guilty pleasure?
  6. What’s your favorite daydream to have?
  7. Have you ever had a one night stand?
  8. Are you a shower or bath kind of girl?
  9. Has anyone ever called you a good kisser?
  10. Have you ever been caught doing something you shouldn’t have been doing?
  11. Have you ever skinny dipped?
  12. What’s your opinion on kissing in public?
  13. Do you prefer boxers or briefs on a guy?
  14. What are you most attracted to in a guy?
  15. What do you think would happen if we were stuck in a room for 24 hours together?

Remember guys, there’s a difference between flirting and being creepy. Here’s a great video from Charisma on Command that explains the difference:

Fun Questions to Ask a Girl

How many times have you heard a girl say she wants to be with a ‘fun’ guy?

This is because everyone loves the feeling associated with being around fun people. And equally, everyone can relate to the drain of being around someone who is boring or overly negative.

Here are some awesome fun questions to show your lighter side.

  1. If you could be a guy for a day, what’s the first thing you’d do?
  2. What’s your favorite 80’s song?
  3. What’s the funniest pickup line you’ve ever had tried on you?
  4. How do clowns make you feel?
  5. Do you prefer a ripped body or a dad-bod?
  6. Who would you rather have dinner with: Tom Cruise or Nicolas Cage?
  7. If you were to make a YouTube channel, what would it be about?
  8. If you had to give up one sense, which would it be?
  9. Who in your life makes you laugh the hardest?
  10. If animals could talk, which animal would you most like to have a conversation with?
  11. Have you ever found someone attractive who you really shouldn’t?
  12. If you were to describe yourself in three words, what would they be?
  13. What’s the most regretful purchase you’ve ever made?
  14. What’s your favorite thing about being a girl?
  15. What’s the weirdest food you’ve ever eaten?

Random Questions to Ask a Girl

Nothing breaks an awkward silence better than a random question. Here are some of our favorites:

  1. Would you rather have a lot of money or find true love?
  2. What’s your favorite day of the week?
  3. What’s a better name for a dog, Milo or Emily?
  4. What’s the most you’ve ever had to drink in a single night?
  5. Would you rather be trapped in a dark small box or at a Justin Bieber concert with no doors or windows?
  6. If you could have any superpower, what would it be?
  7. What’s your favorite animal and why?
  8. Cats, dogs, or llamas?
  9. What do you think of girls proposing to guys?
  10. What’s your favorite song to dance to?
  11. What’s your least favorite food?
  12. What’s the last lie you told?
  13. Are you strangely sentimental about any objects you own?
  14. Have you ever dropped money, noticed, and just kept on walking?
  15. What’s the first thing you do when you get hold of a rubber band?
  16. Do you have a “phone voice”?
  17. Are you a snorer?
  18. Who would you want to play you in a movie about your life?
  19. What do you find yourself hoarding?
  20. Which children’s show did you watch way past an “appropriate” age?

Funny Questions to Ask a Girl

Laughter is the closest distance between two people. – Victor Borge

  1. What would be the first thing you would do if you woke up tomorrow as a guy?
  2. Have you ever been on a blind date that was successful?
  3. What’s your most embarrassing moment?
  4. Tell me about the last time you really laughed, I mean belly-aching, fall-on-the-floor-laughed?
  5. What was the weirdest punishment your parents gave you when you were growing up?
  6. What makes you feel the most awkward?
  7. Where are you most ticklish?
  8. If dolphins are so much like humans, do you think they get thirsty?
  9. What’s something you’re really bad at?
  10. Have you ever been walked in on naked?

Don’t consider yourself to be a “funny” guy?

Check out this video where Stephan Erdman breaks down how to develop a great sense of humor and make women laugh in 3 simple steps:

Questions to Ask Your Girlfriend

These questions are all about strengthening your connection with your girlfriend.

If you’re looking for new things to do with your girlfriend, check out our list of date ideas, as well as our detailed list of vacation spots for couples.

  1. What’s something you’d love to do this month?
  2. What can I do to make your life better today?
  3. What would you like our shared goals to be this year?
  4. In what ways do you feel loved by me?
  5. What are the things I do that you appreciate?
  6. What are the things I do that annoy you?
  7. What’s your favorite thing that we do together?
  8. Is there anything about you that you haven’t felt comfortable telling me?
  9. What’s the first thing that came to your mind the first time you saw me?
  10. How do you think we would fare in a long distance relationship?
  11. What’s something you’d like to do with me that we haven’t done yet?
  12. What do you do when you have the house to yourself?
  13. If I was to be reincarnated as an animal, what do you think I would be and why?
  14. If you could ask three wishes of me, what would they be?
  15. What’s the next place you’d like us to road trip to?
  16. Who out of my friends do you like the most (and why)?
  17. Who out of my friends do you like the least (and why)?
  18. What can I do to help you realize your passions sooner?
  19. What makes you smile about us?
  20. What’s the first thing that you think about when you think of me when we’re not together?

Want more? Click here for 90+ more questions to ask your girlfriend.

Truths to Ask a Girl

Truths are similar to deep questions. They differ in that they specifically put the girl in a position to offer up the most revealing aspects of her past.

  1. When was your last serious relationship?
  2. How long did it last?
  3. Why did you break up?
  4. Who was your first true love?
  5. What do you want to get out of your next relationship?
  6. What would you say is your quirkiest habit?
  7. What is something that not many people know about you?
  8. Have you ever had a run-in with the law?
  9. Have you ever cheated on someone?
  10. What’s the stupidest thing you’ve ever done?
  11. What are you most afraid of in life?
  12. What’s something you have done that you would never tell your parents about?
  13. What’s the craziest dare you’ve ever done?
  14. What’s the worst lie you’ve ever told?
  15. What’s the most un-lady-like thing you’ve ever done?

What Next?

Being interesting, humorous, thoughtful, and inquisitive (in healthy doses) are all super attractive qualities to women. The questions above allow you to subtly demonstrate those qualities without being overbearing or pushy.

Whether you’re looking for love or just seeking to improve your conversations with women in general, having a selection of thought-provoking questions to draw from is an excellent advantage to have.

You don’t want to stop there, though.

Because here’s the number one thing that will help you have better conversations with women.


Like learning to drive or play the guitar, it’s all about how much time you spend on it.

The bottom line?

You need to be speaking to more women than you are right now.

You should also be very aware of the questions not to ask women. Check out our list of those here.

It’s Not Just About The Questions You Ask

Remember this, guys:

Asking the right questions isn’t going to get you anywhere if you smell like your Uncle Dave’s gym sock from 20 years ago.

The truth is, women place much more emphasis on smell than we men do. Enter Pheromone Cologne. It’s an Amazon bestseller with over 3,500 reviews (and most of them positive).

Many guys have said they’ve received positive reactions from women by wearing it.

Give it a try:

Last update on 2020-02-27 / Affiliate links / Images from Amazon Product Advertising API

Use Question Cards to Make Getting to Know Each Other More Fun

If your memory is as bad as ours can be, question cards can work really well as conversation starters.

They’re a fun way to spark awesome conversations and build mutual interest and attraction with the girl you’re interested in. And rather than you being the one asking all the questions, you can take it in turns.

The more she learns about you and shares things about herself, the more she’ll develop a strong intimate bond with you.

We recommend this set from TableTopics:

Last update on 2020-02-27 / Affiliate links / Images from Amazon Product Advertising API

It’s another Amazon bestseller and has sold over 2 million copies. Give it a go. You’ll be surprised by how much fun you’ll both have.

How to Get Out of the Friend Zone

Are you finding that you’re often being “friend zoned” by women?

If so, I urge you to give this book a read. It’s written by a certified marriage, family therapist, and self-described recovering ‘nice guy’.

It’ll teach you how to express yourself and get what you really want in life. It has over 700 five star reviews on Amazon and it’s a total life-changer.

Last update on 2020-02-27 / Affiliate links / Images from Amazon Product Advertising API


To wrap it all up—be present, and show genuine interest in her.

Listen, and stick to open-ended questions. Remember to share your own experiences as well. You don’t want the conversation to come across like an interview.

Chat with us in the comments about any questions we missed, or how you go with trying some of these out. Of course, be sure to visit our homepage for all our latest manly advice.

Additional Resources

Interested in learning more?

Check out these awesome articles that will give you more great tips for becoming a more attractive male:

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