20+ Really Interesting Questions to Ask a Girl You Like


couple talking and drinking coffee

REMEMBER: Below Are 180+ VERY BEST Questions to Attract Her and Keep the Conversation Going! Never Run Out of Things to Say AGAIN! These Tips Helped Over 3,430,000 Readers of THE STALLION STYLE!

When you meet a girl you like, there is one thing you have to do – KEEP HER ATTENTION! Whether you are on a date or just talking on a phone with your girlfriend, silence will always be awkward.

If you suddenly run out of things to say to her, you need to have a list of great backup questions in your mind that will keep the conversation going for hours.

Some are really interesting and funny!

Luckily, I am going to share with you a selection of the best things to ask and what to talk about with a girl. You will love this resource – TRUST ME!

If you are looking for great things to ask your girlfriend, check out this ultimate post here: 90+ Really Good Questions to Ask Your Girlfriend


couple of coffee

1. “What is something you have tried, but will never do again?”
2. “What quirky habit do you have?”
3. “Who is your best friend?”
4. “What is the one thing you did in your past you wish you could undo?”
5. “What is your biggest fear?”
6. “What is the one place in the world you wish you lived in?”
7. “Would you rather be loved or have a lot of money?”
8. “What is the happiest memory from your childhood?”
9. “What is the most embarrassing moment of your life?”
10. “What would your dream date be like?”
11. “What would you change about your personality & look?”
12. “Who has influenced you the most in your life?”
13. “What is something you used to do as a child that you wish you could still do?”
14. “What is the worst thing about dating?”
15. “What is the one career you would love to enter?”
16. “Are you close with your family?”
17. “What is the one movie that influenced your life the most?”
18. “Where is the one place in the world you feel safe?”
19. “What is the one thing you want to experience before you die?”
20. “What is your ultimate goal in life?”
21. “What do you think is your best feature?”

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woman flirting

1. “Which is the first region your eyes would wander to if you were to ever see me naked?”
2. “Have you ever decided to kiss or make out with a guy just because you were horny?”
3. “What is the naughtiest moment in your school days that you can remember?”
4. “If I ask you to ask me to do something naughty what would you prefer the most from me?”
5. “Have you ever had a dream about being a lesbian?”
6. “What do you prefer; thongs or panties?”
7. “While you are kissing, what types of other things you prefer to be done simultaneously?”
8. “Where you do like being touched the most?”
9. “What is your wildest sexual secret that you want to indulge in at least once in your lifetime?”
10. “Have you ever had an unexpected orgasm?”
11. “What’s your favorite thing to do with a guy?”
12. “What kind of wears are you wearing right now?”
13. “If we only had twenty-four hours together, what do you think we’d do?”
14. “Are you a trouble maker?”
15. “What tricks do you use to turn a guy on?”
16. “Where’s your favorite place to get a butterfly kiss?”
17. “What do you find attractive in a man?”
18. “What’s more romantic, or sexy: cooking for someone or dancing with someone?”
19. “What do you think is the number one blunder men make when flirting with or hitting on women?”
20. “What do you think is one thing all men should do when dating?”
21. “Do you believe in love at first sight?”
22. “Have you ever been on a date that totally blew your mind? Like one of those movie moments?”
23. “What’s your weakness/soft-spot in a guy?”
24. “If we only had twenty-four hours together, what do you think we’d do?”
25. “If you had X-Ray vision glasses, would you use them to see under the clothes?”
26. “What do you wear to bed- if anything?”
27. “Do you find yourself more drawn to brains or looks?”
28. “How far can you go on our 3rd date?”
29. “Do you prefer cuddling or making out?”
30. “What would be your perfect romantic getaway?”
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couple on a date

1. “Have you ever sat by the phone all night waiting for someone to call?”
2. “Do you believe that he will always have a special place in your heart?”
3. “Do you believe that everything happens for a reason?”
4. “Have you ever had a crush on a friend’s parent?”
5. “Do you rather follow your heart or your head? State your reasons for your answer?”
6. “Do you prefer to share finances with your partner, or keep them separate?”
7. “Do you sleep with a stuffed toy? What is it?”
8. “Describe the appearance of the person you would like to date?”
9. “Have you ever hated loving someone?”
10. “Do you snore or steal the covers or roll around in your sleep?”
11. “Have you ever had a near-death experience?”
12. “Do you consider it more important to be liked or respected? Why?”
13. “What “most likely to” superlative would you be most honored to receive?”
14. “What is your weirdest dealbreaker?”
15. “Everyone has a mission in life. What do you think your mission is?”
16. “If you could instantly transport just one building to anywhere on earth, what building would you move and where, to create the most interesting outcome?”
17. “When was the last time you literally stopped to smell flowers?”
18. “What was the most uncomfortable thing you’ve had to do out of politeness?”
19. “What view would you most like to have out of your window?”
20. “Would you rather be beautiful and dumb or ugly and clever?”
21. “Where’s the weirdest place you’ve found something that you lost?”
22. “Which famous person would you love to be? Why?”
23. “What is something about life that people don’t appreciate as much as they should?”
24. “What’s the worst thing a person can do that isn’t illegal?”
25. “Have you ever been jealous of your closest friends?”
26. “Who’s your favorite protagonist from an animated movie?”
27. “If you could instantly know how to speak another language, what language would you choose to know?”
28. “What’s the habit you hate most in a boyfriend?”
29. “What’s the best “less is more” example you can come up with?”
30. “What product has greatly exceeded your expectations?”
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1. “What kind of things really makes you laugh?”
2. “What is the most silly pick-up line or a phrase guys used on you to win your attention?”
3. “If you could jump into a pool full of something, what would it be?”
4. “If you had to make out with a friend of the same sex to save the world from aliens, whom would you pick?”
5. “What was the funniest moment in your life?”
6. “Have you ever had a crush on an animated character?”
7. “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?”
8. “Which habit are you proudest of breaking?”
9. “If you had to pick an animal, which animal do you find the sexiest of all?”
10. “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)”
11. “What’s your favorite joke?”
12. “If I caught you masturbating would you carry on, or stop and pretend you weren’t?”
13. “Would you describe yourself as naughty or nice? Why you say so?”
14. “What’s the weirdest nickname you’ve ever had?”
15. “What is your most embarrassing sexual moment?”
16. “Which sexual kink would you be least likely to try?”
17. “What was the strangest punishment your parents ever gave you?”
18. “If people could read your mind, what would they usually hear?”
19. “Did you ever have a crush on your best friend´s boyfriends?”
20. “What would be much better if you could just change the color of it?”
21. “If you could be any fictional character who would it be?”
22. “Do you think you’d know if I was feeling horny?”
23. “What would you do if you could be invisible for one day?”
24. “What food would be the best to make a house out of?”
25. “What’s the weirdest crush you’ve ever had?”
26. “What is the ugliest thing you own?”
27. “What are the best and worst things about being a woman?”
28. “What do you dislike but have no good reason for disliking?”
29. “What’s the first thing you’d look at if you saw me naked?”
30. “What’s the worst thing someone has walked in on you doing?”
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woman talking to a man

1. “What are the things that stand between you and complete happiness?”
2. “When someone sees your name on caller ID, what thoughts and feelings do you want them to have?”
3. “If you were going to die at midnight, what would you be doing at 11:45 pm?”
4. “Standing at the gates of heaven, and God asks you “Why should I let you in?” What do you reply?”
5. “If you woke up tomorrow as an animal, what animal would you choose to be?”
6. “If you could go back in time, once, and change a single thing – what would it be?”
7. “Would your life be better or worse, if you knew the time and place where you would die?”
8. “If you could start over, what would you do differently?”
9. “What habits are holding you back from success?”
10. “What have you done to pursue your dreams lately? How about today?”
11. “What is one dream you think you’ll pursue relentlessly for the rest of your life?”
12. “Do you think human morality is learned or innate?”
13. “Do you think the present is better than 50 years ago? Why?”
14. “If science makes it possible to predict which people will be more likely to commit crimes, should the highest risk individuals be jailed or killed before they can commit crimes?”
15. “What are the most common road blocks that stop people from achieving their dreams?”
16. “What would you change about your life if you knew you would never die?”
17. “What would you have to see to cry tears of joy?”
18. “What makes a person truly evil? Are they born that way or did their environment make them that way?”
19. “How regularly do you see your best friends?”
20. “What will people say at your funeral?”
21. “What would you do differently if you could turn back time?”
22. “If you could watch everything that happened in your life until now, would you enjoy it?”
23. “What is the hardest lesson you had to learn in life?”
24. “What would you do differently if you knew that no one was judging you?”
25. “Do you believe everything happens for a reason, or do we just find reasons after things happen?”
26. “How do you celebrate the things you do have in your life?”
27. “In your life, what has been the biggest blessing in disguise?”
28. “When you’re 90 years old, what will matter most to you in the world?”
29. “If you could write a note to your younger self, what would you say in only three words?”
30. “How much is a human life worth and are some lives worth more than others?”
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girl riding a bike

1. “What’s your favorite book and why?”
2. “What would you grab if your house was on fire?”
3. “What was your favorite childhood toy?”
4. “What was your worst job?”
5. “What does your name mean?”
6. “How do you spend your free time, and where do you like to go?”
7. “What role models do you respect the most?”
8. “Where were you born?”
9. “What’s one thing on your bucket list?”
10. “Are you a troublemaker?”
11. “Who is your best friend and what do you love about him/her?”
12. “Do you have any nicknames?”
13. “What’s one place you really want to travel to?”
14. “What makes you really irritated? Especially something other people do that irritates you!”
15. “Is death your biggest fear, or is it something else?”
16. “If you were a man for a day, what would be the first thing you do?”
17. “What’s one thing that’s happened to you that has made you a stronger person?”
18. “What’s one thing you’d love to learn more about?”
19. “Where is one place you feel most like yourself?”
20. “What is something you’ve never done that you’ve always wanted to do?”
21. “Where is your favorite place to escape to?”
22. “What is something you’ve never done that you’ve always wanted to do?”
23. “If you could change one thing about yourself what would it be?”
24. “What is your biggest fear?”
25. “When you were younger what did you think you were going to be when you grew up?”
26. “What is the craziest thing you’ve ever done?”
27. “Do you easily accept compliments? Or do you hate compliments?”
28. “If you could be any animal, what animal would you be?”
29. “How seriously do you take horoscopes?”
30. “Do you have any regrets? What’s your biggest one?”
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couple on first date

1. “How is your relationship with your mom?”
2. “Do you have any brothers or sisters?”
3. “What do you value the most when it comes to friendship?”
4. “How is your relationship with your father?”
5. “How often do you talk with your parents?”
6. “What’s your best memory with your father/mother/sibling in it?”
7. “What jobs did your grandparents do?”
8. “Who do you think knows you the best?”
9. “Where is your bloodline originally from?”
10. “How regularly do you see your best friends?”
11. “How is your relationship with your father?”
12. “Tell me about a funny family story.”
13. “Which relative are you emotionally closest to?”
14. “Where did your parents meet?”
15. “Who is the wisest person in the family?”
16. “If you had to choose, what family member would you kill off and why?”
17. “Tell me about a family member you are really proud of.”
18. “Who’s your best friend?”
19. “Where is your bloodline originally from?”
20. “How did you and your best friend meet?”
21. “Who is the kindest person in your family?”
22. “What’s the most immature thing your parents do?”
23. “Who is the wisest member of your family?”
24. “What’s the weirdest tradition your family has?”
25. “What bad thing did you do as a kid that your parents never found about”
26. “What’s your “and then it got worse” family story?”
27. “Do you have any relative in jail?”
28. “Do you have any famous relatives?”
29. “How close are you with your family?”
30. “What jobs do your parents do?”
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the best sex story

1. “Does a massage make you wet?”
2. “Would you use sex toys?”
3. “Do you like watching porn?”
4. “Which celebrity would you sleep with in a blink of an eye?”
5. “Doggy style or a cowgirl?”
6. “Will you cheat on your boyfriend with an ex whom you still have strong sexual chemistry with?”
7. “Does size matter to you?”
8. “Would you be open to a threesome?”
9. “If a guy wants to come over to your place and make out with you right now, would you like that?”
10. “Where was the craziest place you ever had sex?”
11. “Have you ever kissed a girl before?”
12. “Spit or swallow?”
13. “If I asked nicely, would you show me your boobs?”
14. “Have you ever been caught having sex?”
15. “How often do you masturbate?”
16. “What makes you wet without fail?”
17. “What’s the dirtiest thing you’ve ever sexted someone?”
18. “What’s your favorite part of a man’s body?”
19. “What’s the most daring place you’ve done it in public?”
20. “Who’s the one person in this world you wish you could fuck?”
21. “In what position to you orgasm most reliably?”
22. “What does it feel like when you orgasm?”
23. “Have you ever made an erotic fantasy come true?”
24. “Are you a screamer? A moaner?”
25. “How do you like your pussy to be licked?”
26. “What’s your favorite kind of foreplay?”
27. “Do you like it rough or gentle?”
28. “If you had to choose, would you be a dominatrix or a submissive?”
29. “What does your ideal penis look like?”
30. “What’s your favorite blowjob technique?”
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couple talking and laughing

1. “What’s your favorite place in the entire world?”
2. “Where did you go to school?”
3. “What do you do, and how long have you been doing it?”
4. “What were you like as a kid?”
5. “What’s on your bucket list?”
6. “What type of music are you into?”
7. “Do you have any nicknames? What’s the story behind them?”
8. “Are you a cat person or a dog person?”
9. “Did you like this place?”
10. “Want to get coffee/dessert after this somewhere else?”
11. “What kinds of things really make you laugh?”
12. “Have you figured out your calling in life? What is it?”
13. “What’s your favorite place in the entire world?”
14. “Favorite movie of all time? Why so?”
15. “What is your favorite way to spend a Saturday?”
16. “What do you hate most about the dating process?” (Tell me so I can avoid it!)
17. “What type of music are you into?”
18. “Do you have any pet peeves?”
19. “Do you ever cook?”
20. “What’s your biggest goal in life right now?”
21. “Coffee or tea?”
22. “Who was your favorite schoolteacher or college professor? Why?”
23. “Are you a morning person or a night person?”
24. “Who is your best friend? What do you like about him/her?”
25. “What are you most passionate about?”
26. “What was your major?”
27. “What should I know about you that I’d never think to ask about?”
28. “If you won the lottery tomorrow, what’s the first thing you’d buy?”
29. “Who has been the biggest influence in your life?”
30. “What was your family like growing up?”
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the crazy psycho woman

1. “How old are you?”
2. “How much do you weigh?”
3. “Are they really yours?”
4. “Why do you have to be a b*tch sometimes?”
5. “Do you think I’m handsome?”
6. “Are you on your period?”
7. “Do you want to know what my ex did this one time?”
8. “Want to pay for dinner?”
9. “Can I read your messages?”
10. “How many guys have you slept with?”
11. “Babe, I bet if you were a guy, you’d f*ck her brains out too, right?”
12. “What do you think of my uh, size?”
13. “Is your sister hot?”
14. “Can I borrow some money?”
15. “Are you really going to eat all that?”
16. “How long does it take to put on all that make-up?”
17. “If I got you pregnant, would you have an abortion?”
18. “How much do you earn?”
19. “Can you chill?”
20. “Why can´t you lose weight?”
21. “How did you screw-up your last relationship?”
22. “Is it that time of the month?”
23. “Can you calm down?”
24. “Do you like to be conquered?”
25. “Why do you like wearing that skirt?”
26. “Are you drunk yet?”
27. “If you could have dinner with any famous person, living or dead, would you order the most expensive entrée on the menu like you did tonight?”
28. “I’m going to get some food, do you want a salad?”
29. “If you could change 3 things about yourself, would you start with that nose?”
30. “Why are you even friends with them?”
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Hey folks! I am James (a.k.a. Stallion) and I want to make this THE GREATEST place for every guy to master the arts of love, dating and attraction! I am young, free and my motto is "Carpe Diem".
  • Dave

    I would like to add that something that should be discussed is belief systems – or rather, world views. People think they can have polar opposite world views and make it work. It is VERY rare for this to happen, and when it does, usually both have agreed on everything else which makes things tolerable.

    • Thanks for adding this question to this list. It is worth considering.

  • Sandy

    I really enjoyed this list, coming from a woman’s point of view. The questions are easy, yet deep, and allow for an open conversation where you can be open or closed off as you like. I don’t like to feel like a man is pressing me for answers. Yuck!

    • Thanks a lot for your feedback Sandy. I am glad you liked it.

  • Tina

    Okay, so I know this is a bit much, But I think men should discuss children on the first date. As a single mother, I have been on a few dates where children weren’t brought up until the end when I jut had to say it and the men were weird with me, as if I was hiding it. A few never called me after the first date. So, talk about children, men. Even if you touch lightly on the subject.

    • Hey Tina, that is nice addition as well. One should definitely clear all family relations during first dates.

    • Pat

      Why do you expect men to start talking about children? Why wouldn’t you mention children if that is on your mind? We are not mind readers.

  • John

    This reminds me of 21 questions. I played with when I was in high school with girls. I have been on dates where I didn’t know what to ask, or how to work things the right way. I don’t want to come off as a douche to a woman so I tend to be more quiet, which I guess can make me seem uninterested. Ugg. This list helps!

    • You are welcome. Definitely, with this list you will be able to avoid that awkward moment of silence when both of you do not know what to say or ask.

  • Dale

    Going to keep this bookmarked. I am horrible on dates so for someone like me this is useful. Some of the questions I feel are a bit much for a first date, but some of the others are great conversational starters both I, and my date can speak on.

    • That is great to know Dale. I bet you should learn some basic topics of conversation with girls.

  • Jenny Stone

    If a man asked me about my family on a date, brownie points to him! 😀
    I am very close with my family so finding a man who is equally family oriented as I is a tough cookie. Also, asking about goals in life is great. It shows interest and allows the man to get to know the special lady he is interested in.

    • Thanks for pointing out strong points within this list.

  • Sara

    I might be a bit young for this, but if the boy I liked at school asked me these questions, I would feel so good! I have a hard time relating to boys to begin with, I don’t even know what to say. I need a boy that will ask questions like these so I don’t have to keep second guessing. I am not a mind reader!

    • Sure, younger boys are really pathetic at communicating. By the way, thanks for your kind words about this post.

  • G. Williams

    I once met a beautiful woman at work. I was instantly attracted to her. I had no idea what to say or how to even approach her. I casually made small talk with her. I actually asked her a few questions from this list and when I did, she lit up. After about 2 weeks of getting to know her, and still not having the balls to say I liked her, she asked ME out! Needless to say, the right questions make all the difference. That woman is now my wife of 8 years.

    • This is amazing story! Thanks a lot for sharing this with all of us…

    • bravo

      dude cani know what type of question did you ask her? i scared if i ask a topic thats if at the top but irrelevant to her then it will be a big akward moment then 🙁

  • Simon Gray

    I agree with a few of the other people that posted… Children and religion should be brought up at some point. You don’t want to get intimate or being a relationship with someone who doesn’t want kids, or if they don’t believe in God (assuming you want kids and you do believe). That is a recipe for disaster! My best bud is going through a divorce because they didn’t discuss things like this and jumped head first into marriage.

    • You are talking some real sense here. Thanks Simon these are some points worth repeating.

    • jakob robinson

      You wouldnt date someone because they arent religous ? I think you shouldnt date someone who is religous who wants there kids growing up brainwashed believing in nonsense bedstories pfttt.

      • Shibu Yokomola

        It’s not about religion but having the same believe system will help reduce tensions in the house even if both have different religions. What matters is the truth and learning to search the truth with an open and humble mind is the best believe system.

  • vism

    I usually ask the girls “What gives you power?”

    • Klaus Frey

      That’s an interesting question. What kind of responses do you get?

  • Gavin

    The what animal is the sexiest one didn’t work. I don’t think she liked it at all and it created a very awkward situation

  • prasetyoadiekyy

    its very good article:)

  • Alex Momeni

    how do you go about when the girl wants to know if you were married or have kids within her first few questions? Before anything starts, some how these two questions keeps coming up for me.

    • Craig Johnston

      i guess if they ask be honest and tell them, you will know with there reaction how they feel about that. if she likes you it wont be a problem 🙂

  • Abortus Deradelphus

    Seriously what are some of these questions? Lol! Some are what creeps would ask if they just met a female.

  • Hussnain Fida

    These question are very interesting. I like so much.

  • Harsh malviya

    Heyy stallion that stuff above is truly mind blowing. Thank you so much brother.

  • Name:Fireman

    It makes sense to ask a girl noble questions.Sometimes guys end up asking the wrong question and it cost them a lot.
    It is always good to calculatively construct a question and meticulously inquire thereof.Big ups to all relationships out there.
    Keep up with effective communication.