21 Questions to Ask a Girl You Like That Will Blow Her Mind

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by  Dean Stephens | Last Updated:  Jul 23, 2020
Guy looking at a girl as they walk down the street

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

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.

Why?

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 you can convey these traits to her with questions.

But remember guys:

You also want to mix in a healthy dose of statements and stories so 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 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.

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 best questions to ask a girl.

1. What are you most passionate about right now?

Have you ever been chatting with someone and you mention something that makes their entire face light up with excitement?

Chances are you’ve stumbled upon a topic they’re passionate about. People love talking about their passions. If you’re the one who gets her talking about the things she’s most excited about, she’ll always associate those positive feelings with you.

And you don’t need me to tell you why that’s a good thing, right?

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

Life can only be understood backwards, but it must be lived forwards. Søren Kierkegaard

I like this question because it lets you know how much she dwells on the past.

3. Have you traveled much (or do you want to)?

This is a great question for two reasons:

  1. If you’re a guy who loves to travel, you’ll quickly understand how compatible you are in the globetrotter department; and
  2. You’ll know how to steer your future conversations with her. If you’re both well-traveled, you’ve instantly got a goldmine of topics to draw from. If she hasn’t traveled much, but she wants to, then you can be her very own international man of mystery. If she’s not a fan, then reconsider talking any further about travel.

4. What’s your biggest deal-breaker in a relationship?

Is her ultimate deal-breaker something you agree with? This question also raises the idea in her head about what it’d be like to be in a relationship with you.

I think this is a good time to to mention this. The key to creating powerful connections with women is to attract them without faking behavior, lying, or pretending to be someone else.

In short, you need stop acting like an attractive man and become one. To do this, you need to learn to be vulnerable, honest, and to set boundaries.

The book that completely changed my life by driving this home is Models by Mark Manson:

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What I like most is that it’s based on scientific research and it’s completely different to so many other dating books out there for men. It’s not about “picking up”. And it’s not about treating women as exploitable objects.

It’s for real men who are ready to cut the games and project their honest and authentic selves.

Models should be required reading for all men. I know I wish I had of read it when I was straight out of high school.

5. What was the last crazy adventure you went on?

Want to know how much of a thrill-seeker she is? Ask this question.

The more adventurous she is, the more direct you can be in your conversation and the quicker you can escalate your relationship. On the flip side, if she’s more conservative, you’ll want to take things slower.

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

This helps you find common ground and brings you closer through understanding her better.

It also helps you weave in some playful teasing later if she complains about being hot or cold.

7. Is [what she’s focusing on now for school/work] what you want to do forever?

One word—ambition. If she’s content with her average 9-5 job, it’s probably best to cool it on the empire-building chat.

Conversely, if she has dreams of curing cancer, don’t expect her to be attracted to you if your ambitions don’t go beyond beating that next level in Halo.

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

This is an excellent general question to build comfort with her.

If she’d like a family of her own someday, it could also give you some insight into what kind of place she’d like to raise it.

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

This is a fun question. You’ll find out what’s at the very top of her bucket list.

Who knows, maybe you could be the guy that could make it happen for her?

10. What do you like most about yourself?

Be careful with this one, you need to time it right so you don’t put her on the spot.

This helps you understand her core values and how comfortable she is talking positively about herself. Be sure to offer the same up for her because this is a vulnerable share.

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

Building a connection with a woman includes getting to know her interests. And let’s be real, almost everyone watches movies.

I like to throw this one in as a lighter question to switch things up from a serious topic that’s run its course.

12. What are you most proud of?

The answer to this question will tell you what has been the most important moment in her life to date. This is a great time to share how you relate to it (if you can).

13. Do you have any secret talents?

The more things you can learn about her that others don’t know, the closer she’ll feel to you.

14. What is your wildest fantasy?

Imagination is everything. It is the preview of life’s coming attractions. Albert Einstein

This is a great flirty question. It builds sexual tension and uncovers many fun roleplay scenarios for you to explore with her.

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

I love asking people this question (yes, not even just girls) because you can relight the fire under someone’s interest or hobby that they may have forgotten about or let slip away.

Also, if she picks that thing up again, she’ll always remember you whenever she does it.

16. What were you like as a kid?

Was she a bookworm? Cheerleader? Total jerk?

Her answer can lead you in so many directions for a fun conversation. Would she have been your nemesis? Tease her about it.

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

You’ll learn what she values most in the world. While you don’t want to judge her entire character based on one question, if it’s a physical item then you know she may be more materialistic than other girls.

If it’s her cat, then you know she’s a huge animal lover. You get the idea.

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

This one’s all about putting your double agent hat on. Her answer to this can help you guide the dates you plan with her.

Don’t literally plan the exact date she mentions the next time you hang out, as that’s way too obvious. But if she says a picnic in the park, maybe keep skydiving in your back pocket for now.

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

I like this question for a few reasons:

  1. You’ll probably learn a new piece of advice that may prove valuable to your own life; and
  2. It gives you some insight into how thoughtful she is and how willing she is to open herself up to advice from others.

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

Where you live plays a huge role in the life you lead. Her answer to this question will help you understand how happy she is with where she lives right now, as well as her ideal type of place to be.

Does it marry up with yours? Be sure to share your own. Talking about the future with a girl forces her to envisage you being in her future. Cool trick, right?

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

This helps you get a feel for the role she plays in her closest friendship circle and her perception of her own personality.

You can use her answers as ammunition for plenty of playful teasing.


100+ Good Questions to Ask a Girl

Hungry for more questions?

You got it.

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

20 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.

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:


15 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 one day?
  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:


15 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:


15 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:


15 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?

20 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?

10 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:


20 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? Here are 90+ more questions to ask your girlfriend.


15 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 demonstrate those qualities without being overbearing.

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.

Practice.

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.

Further reading: 20 Questions A Man Should Never Ask A Woman (And The Reasons Why)

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:

TableTopics Original - 10th Anniversary Edition: Questions to Start Great Conversations Check Best Price on Amazon
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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.

Stop Being So “Nice” and 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 (or listen, the audiobook is great):

No More Mr. Nice Guy: A Proven Plan for Getting What You Want in Love, Sex and Life (Updated) Check Best Price on Amazon
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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—it’s a total life-changer.

Conclusion

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. Be sure to visit our homepage for all our latest manly advice.

Interested in learning more?

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