100 Intriguing Questions To Ask A Girl

When you're first getting to know a girl, one of your biggest weapons is questions.

Questions not only give you deeper insights into the girl you're dating, but they also help her to open up, and they can make her interested in you

After all, girls want to be asked interesting questions that excite them and start conversations and help them explore each other.

But we get it: Some questions are more interesting than others. While some can help you learn more about the girl you're dating so that you understand whether or not she's the right one for you, others tell you very little – and they can also make her feel awkward, uncomfortable, or even bored.

To help you ask the right questions while avoiding small talk, we've gathered together the best 100 questions to ask a girl. Let's take a look. 

Questions To Ask A Girl About Her Life

1. What's your biggest life lesson so far?

Find out how much she's grown.

2. Are you currently where you planned to be 5 years ago?

Is she on track, or did something happen in her life that took her off-course? 

3. Where do you see yourself in 5 years?

Find out whether she prefers to plan or just go with the flow. 

4. What's your biggest regret?

Learn what she's done in the past that she wouldn't do today. 

5. What's your best quality?

How does she feel about herself?

6. What's your worst quality?

You need to know what is most disagreeable about her before you properly start developing feelings. 

7. Do you believe in fate?

It's important to know how aligned the two of you are when it comes to things like spirituality.

8. What is the meaning of life to you?

This is a deep question, but sometimes you need to go deeper to learn about a person fully. 

9. Are you religious?

Again, it's key that you understand how aligned the two of you are in such matters. 

10. What quote do you live by?

Knowing what quote she likes will give you major insights into her values. 

11. Is there something you will not accept under any circumstances?

This is another question related to values that's important to know. 

12. Is there something you could never live without?

We all have things we hold dear to our hearts – and find out what hers is. 

13. Which person changed your life?

She might say no one has changed her life, but it's still worth asking this question.

14. When are you at your happiest?

Finding out what makes her happy will make it so much easier for you to make her happy. 

15. What makes you angry?

Same as above. If you know what makes her angry, you can do the right things that ensure she doesn't get angry often. 

16. Are you an optimist or a pessimist?

Ask this to see if the two of you are the same or opposites.

17. Do you like living life to the fullest?

See whether or not she loves life as much as you do!

18. Is there one day that changed your life forever?

We've all had a moment that changed who we are – find out what hers was. 

19. What one thing would make your life better right now?

Maybe that one thing is you? 

20. If you could swap lives with anyone, would you?

Ask this question to find out how comfortable she is with her own life.

Questions To Ask A Girl About Her Family

21. Are you close to your family?

Especially if you're close to your own family, questions like this are important.

22. Do you get along with your family?

How well a girl gets along with her family can tell you a lot about how she handles relationships and friendships.

23. Do you have any siblings?

This is just a basic general interest question that will help you learn more about her background.

24. Who do you get along with the most in your family?

It could be that she gets along with her grandmother more than her parents.

25. What do your parents do?

Again, it's just a general interest question, but it helps to sketch in a bit of background about her and her family.

26. Do you usually introduce your boyfriend to your parents?

Some girls do this; some don't. Find out how she feels about it. 

27. What's your happiest memory with your family?

Ask this to open up happy memories (and positive feelings) inside her. 

28. Did your parents encourage you to do things?

How her parents behaved towards her will tell you a lot about her own personality.

29. What's your earliest childhood memory?

This is just a fun question that can get the two of you talking about the joys of childhood. 

30. Did your parents used to punish you?

Such a question can give you insights into why she reacts the way she does to things. 

31. Are you family-oriented?

This is a super important question to ask if you're family-oriented yourself (or if you aren't). 

32. When did you move out of your parent's house?

How long has she been independent for? 

33. How often do you see your parents?

And would she like to see them more? Or less? 

34. Are you most like your mom or your dad?

Knowing who she takes after the most will give you a clue as to what her own traits are. 

35. What's the best thing about your family?

Help her help you fall in love with her family!

36. What's your mom's best quality?

Hey, one day you might meet her mom, so it's better to know more about her now!

37. What's your dad's best quality?

See above. 

38. What is the best thing about your family?

This is just a nice question to ask!

39. Is it important that anyone you date gets along with your parents?

You need to be prepared for things like this if you start to date her long-term. 

40. Do your parents want you to get married?

Knowing the answer to this question will help you understand where her head is at when it comes to things like marriage.

Personal Questions You Can Ask a Girl

41. Are you good at saving money?

This is a key question related to finances that will matter a lot if you're to date over the long term.

42. Do you have any bad habits?

She most likely won't share her worst habits straight off the bat. 

43. What would you change about yourself if you could?

Girls actually don't mind talking about the things they don't like about themselves. 

44. How are you with compliments?

Find out whether or not she'll gladly accept your compliments!

45. Are you argumentative?

You may as well find out sooner rather than later!

46. What's the worst thing you've ever done?

She might say, “I'll come back to this one.”

47. What's your biggest regret?

This isn't an easy question for her to answer – but she'll appreciate it all the same, and it will get her thinking. 

48. What's your favorite quality in a man?

Find out whether you possess it!

49. Do you like to step out of your comfort zone?

Ask this question if you love to step out of yours. 

50. Do you have any vices?

Find out whether she has vices that you strongly disagree with. 

51. What's the worst first date you've ever had?

This should yield a humorous answer that you can both giggle over. 

52. Have you ever been close to dying?

Only ask this question when the moment/mood is right. 

53. If the world ended today, would you be happy with what you've done so far?

Damn – you're really going deep with this one!

54. What would make your life perfect right now?

This question will give you major insights into what her relationship goals are like at the moment.

55. Are you happy with who you are?

This is another deep, introspective question that will help the two of you form a closer bond. 

56. What's the weirdest thing about you?

Hey, you've gotta learn this stuff at some point! 

57. Do you have secrets?

She doesn't need to share them, but you'll want to know if you're dealing with a secretive person or not. 

58. If you could live in a book, which one would it be and why?

This question will tell you more about what kinda life she'd love to lead if it was possible.

59. What personality type are you?

It'll be amazing if the two of you complement each other. 

60. What's your worst personality trait?

Maybe she's super lazy? 

61. What do you hate most about other people?

Find out whether or not you possess the personality trait she hates! 

Questions To Ask A Girl About Her Work

62. Do you enjoy your job?

Talking about her job can be boring for her, but it's still a good idea to see how she feels about her work.

63. What did you want to be when you were young?

Learn more about her hopes and dreams. 

64. How did you end up in this profession?

People always have interesting stories to tell about how they ended up in the profession they're in.

65. If you could do anything work-wise, what would it be?

And encourage her to achieve her goals!

66. Do you get along with your colleagues?

If you start dating, she will talk about her colleagues anyway. 

67. What do you love about your job?

Even if she hates her job, make her feel positive by encouraging her to talk about the good stuff.

68. What do you hate about your job?

Once she starts answering questions like this, she will soon open up to you more and more about her life at work. 

69. What's more important for you in a job, money or job satisfaction?

This question will give you huge insights into what her priorities in life are. 

70. Would you retire early if you could?

Find out whether she's married to her work or whether she just wants to relax. 

71. Is it important that you date a man with a good job?

This is a key question to ask in terms of your compatibility. 

72. What was your first job?

There are always funny stories to tell about our first job!

73. What was your favorite job?

Again, this question can cause her to share some really interesting and funny stories. 

74. What skills have you learned over the years through working?

Maybe she has skills that will prove useful for the two of you? 

75. Would you like to launch your own business one day?

This question will help you find out how ambitious she is. 

76. Would you date a guy who didn't work?

Even if she says Yes, her reasons might be complex. 

78. What's the most amount of hours you would work in a week?

Especially if you're not a workaholic, these types of questions are important to ask a girl. 

79. Would you go back to school?

Going back to school is a big decision as we get older.

80. Do you have a good work-life balance?

Or does she find it hard to make time for dating?

81. Where do you see yourself in 5 years in terms of work?

The clearer her vision is, the more you'll know whether or not you're compatible. 

82. Have you dated a colleague before?

This could be an interesting question …

83. Do you have any funny job interview stories for me?

Not all questions need to be serious! 

Questions To Ask A Girl About Her Goals

84. Do you like to write down your goals?

This will tell you how much achieving things in life matters to her. 

85. What's your biggest dream right now?

Find out what she really wants out of life. 

86. Do you usually follow your goals through to the end?

Or does she quit? 

87. Are you a motivated person?

This is a key question when it comes to compatibility. 

88. Could you be with someone who isn't ambitious?

Her answer will speak volumes about her own values. 

89. Do you love a challenge?

Or does she prefer to be conformable?

90. Tell me about the biggest struggle you overcame.

This question will cause her to think hard, and her answer could bring the two of you close together. 

91. Are you a perfectionist?               

They say that perfectionists can be hard to get along with. 

92. Are you a morning person or a night person?

If you're both opposites when it comes to this, you might struggle to take things forward.

93. Who inspires you the most?

It's always nice to find out who inspires our partners. 

94. Do you strive to do as much as you can in one day?

If she's a go-getter in life, it'd be awesome if you're the same. 

95. Do you think patience is a virtue?

People are either super patient or impatient – find out what she is.

96. What's your most realistic goal right now?

And is it compatible with your most realistic goal?

97. What do you want most in life professionally?

Find out if her professional goals align with yours. 

98. What do you want most in life personally?

Find out if her personal life goals align with yours. 

99. Do you have discipline?

Disciplined people can be really easy to get along with.

100. Would your goals change if you met someone you fell in love with?

This is a huge question that's mega important to ask. 

101. Is there anything stopping you from achieving your current goals?

Maybe you could help her if there is. 

102. What's your proudest moment so far?

Share in her proudest moment!

103. What goals do you regret not following through on?

What would she have achieved if she'd really gone for it?

About Will Titterington

Will is a writer, coach and life lover who enjoys helping people reach their potential. Will has plenty of experience with Online Dating. He loves to test different apps and sites and share his experience on DatingXP. He loves art, sports, connecting with new people from all over the world, and making people laugh.