20+ Really Interesting Questions to Ask a Girl You Like

two georgeous girls talkingREMEMBER: Below Are 60 VERY BEST Questions to Attract Her and Keep the Conversation Going! Never Run Out of Things to Say AGAIN! These Tips Helped Over 3,152,000 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!

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

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!

21+ Good Questions to Keep Her Interested & Curious by THE STALLION STYLE!

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?”

10 Flirty Questions to Make Her Fall for You!

flirty woman with lollipop21. “Which is the first region your eyes would wander to if you were to ever see me naked?”
22. “Have you ever decided to kiss or make out with a guy just because you were horny?”
23. “What is the naughtiest moment in your school days that you can remember?”
24. “If I ask you to ask me to do something naughty what would you prefer the most from me?”
25. “Have you ever had a dream about being a lesbian?”
26. “What do you prefer; thongs or panties?”
27. “While you are kissing, what types of other things you prefer to be done simultaneously?”
28. “Where you do like being touched the most?”
29. “What is your wildest sexual secret that you want to indulge in at least once in your lifetime?”
30. “Have you ever had an unexpected orgasm?”

10 Witty Questions for Better Conversation!

flirty questions to ask each other31. “Have you ever sat by the phone all night waiting for someone to call?”
32. “Do you believe that he will always have a special place in your heart?”
33. “Do you believe that everything happens for a reason?”
34. “Have you ever had a crush on a friend’s parent?”
35. “Do you rather follow your heart or your head? State your reasons for your answer?”
36. “Do you prefer to share finances with your partner, or keep them separate?”
37. “Do you sleep with a stuffed toy? What is it?”
38. “Describe the appearance of the person you would like to date?”
39. “Have you ever hated loving someone?”
40. “Do you snore or steal the covers or roll around in your sleep?”

10 Funny Questions to Make Her Smile

couple discussing funny things41. “What kind of things really makes you laugh?”
42. “What is the most silly pick-up line or a phrase guys used on you to win your attention?”
43. “If you could jump into a pool full of something, what would it be?”
44. “If you had to make out with a friend of the same sex to save the world from aliens, whom would you pick?”
45. “What was the funniest moment in your life?”
46. “Have you ever had a crush on an animated character?”
47. “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?”
48. “Which habit are you proudest of breaking?”
49. “If you had to pick an animal, which animal do you find the sexiest of all?”
50. “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)”

10 Thought Provoking Deep Questions That Will Take Her Breath Away

couple asking deep questions51. “What are the things that stand between you and complete happiness?”
52. “When someone sees your name on caller ID, what thoughts and feelings do you want them to have?”
53. “If you were going to die at midnight, what would you be doing at 11:45 pm?”
54. “Standing at the gates of heaven, and God asks you “Why should I let you in?” What do you reply?”
55. “If you woke up tomorrow as an animal, what animal would you choose to be?”
56. “If you could go back in time, once, and change a single thing – what would it be?”
57. “Would your life be better or worse, if you knew the time and place where you would die?”
58. “If you could start over, what would you do differently?”
59. “What habits are holding you back from success?”
60. “What have you done to pursue your dreams lately? How about today?”

10 Questions to Know Her Better

image of woman with bike61. “What’s your favorite book and why?”
62. “What would you grab if your house was on fire?”
63. “What was your favorite childhood toy?”
64. “What was your worst job?”
65. “What does your name mean?”
66. “How do you spend your free time, and where do you like to go?”
67. “What role models do you respect the most?”
68. “Where were you born?”
69. “What’s one thing on your bucket list?”
70. “Are you a troublemaker?”

10 Questions to Know Her Family & Friends

couple talking to each other71. “How is your relationship with your mom?”
72. “Do you have any brothers or sisters?”
73. “What do you value the most when it comes to friendship?”
74. “How is your relationship with your father?”
75. “How often do you talk with your parents?”
76. “What’s your best memory with your father/mother/sibling?”
77. “What jobs did your grandparents do?”
78. “Who do you think knows you the best?”
79. “Where is your bloodline originally from?”
80. “How regularly do you see your best friends?”

10 Questions to Reveal Her Dirty Secrets

flirty couple teasing each other81. “Does a massage make you wet?”
82. “Would you use sex toys?”
83. “Do you like watching porn?”
84. “Which celebrity would you sleep with in a blink of an eye?”
85. “Doggy style or a cowgirl?”
86. “Will you cheat on your boyfriend with an ex whom you still have strong sexual chemistry with?”
87. “Does size matter to you?”
88. “Would you be open to a threesome?”
89. “If a guy wants to come over to your place and make out with you right now, would you like that?”
90. “Where was the craziest place you ever had sex?”

10 Questions to Ask Her on a First Date

young man and woman talking to each other91. “What’s your favorite place in the entire world?”
92. “Where did you go to school?”
93. “What do you do, and how long have you been doing it?”
94. “What were you like as a kid?”
95. “What’s on your bucket list?”
96. “What type of music are you into?”
97. “Do you have any nicknames? What’s the story behind them?”
98. “Are you a cat person or a dog person?”
99. “Did you like this place?”
100. “Want to get coffee/dessert after this somewhere else?”

THE STALLION STYLE Bonus #1: Questions You Should NEVER ASK Any Girl

angry and furious woman1. “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?”

THE STALLION STYLE Bonus #2 – Further Resources for Better Conversation

THE STALLION STYLE Bonus #3 – 30 Ultimate Signs of Attraction

image of attraction

Source: Seduzioneattrazione.com

Read this next to see if a girl likes you or not, this is the next step you have to keep in mind: 8 Sure Signs That a Girl Likes You and this one here: 18 Great First Date Ideas to Spark Attraction


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.

    • http://thestallionstyle.com/ James Buzinko

      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!

    • http://thestallionstyle.com/ James Buzinko

      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.

    • http://thestallionstyle.com/ James Buzinko

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

  • 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!

    • http://thestallionstyle.com/ James Buzinko

      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.

    • http://thestallionstyle.com/ James Buzinko

      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.

    • http://thestallionstyle.com/ James Buzinko

      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!

    • http://thestallionstyle.com/ James Buzinko

      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.

    • http://thestallionstyle.com/ James Buzinko

      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.

    • http://thestallionstyle.com/ James Buzinko

      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?”

  • 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

  • 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:)

  • 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.

  • 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.