100 Deep, Personal Questions to Ask a Girl to Create a Deep Connection

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Girls are known to be deeper than boys.

They generally need depth and long lasting interest to keep their attention.

They want to be asked questions that delve under the surface of the body.

deep questions will make a girl love you

If you’re starting a relationship you can find good questions to ask your girlfriend here and if you’re going on a first date look no further than here.

Below, you will see 100 personal questions to ask a girlfriend to get to know her deeply.

Table of Contents

1. What event has had the largest impact on your life?

She will scan her brain for one of her top things or list a few things that have made her her.

2. How did your Mother and Father raise you?

This one is tough… maybe she was raised by a single mother, maybe she had the seemingly perfect family…

3. Do you have siblings and where do you fall on the birthing?

Is she the middle child, the oldest or the youngest? This truly makes a difference.

4. Who would you die for?

The people she loves? Anyone? Nobody? See how she answers this and how big she loves others and puts others above herself.

This may be the best question to ask if you really want to get to know her and make her your girlfriend.

asking personal questions to a girl will let you see a whole another side to her

5. If you could meet anyone in the world, dead or alive, and spend a day with them who would it be?

Will she name a celebrity or a biblical figure like Jesus?

6. If you could go back in time where would you go and why?

Back into her own life or back into dinosaur times?

7. If you could choose anyone to have dinner with who would it be and why?

Or any historic dinner party to attend, who’s would it be?

8. Do you think the future will be better or worse than the present?

Optimistic, pessimistic, or realistic? Does she see the glass half full, half empty or refillable?

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9. Do you think humans are born good, evil, or neutral?

Does nurture really determine exactly who you are going to be? Or is it a mix?

10. What is the most important quality of a successful relationship?

Hopefully she names things like honesty, comprehension, loyalty, etc.

11. What keeps you up at night when you can’t sleep?

Anxiety, insomnia, a list of all the things she wanted to get done but did not have time for?

12. Do you have any recurring dreams?

Those are inner battles she will need to face.

a guy asking a girl deep, flirty questions which makes her kiss him

13. What is your biggest fear? No spiders don’t count…

Is it never being loved the way she needs to be loved? Is it holding on when everyone else has let go? Really uncover her fears so that you can understand the way her brain works, or at least try to.

14. Have you ever left the country?

How big is her desire for wander? Does she need to flee home to feel whole?

15. What is the most traumatic event from your life?

Think back to your own and she probably has a similar story from her childhood. Deep questions create everlasting bonds.

16. What do you think your parents regret about the way they raised you?

Were they too impatient, too hard on her, or did they try and be a friend instead of a parent?


17. Do you hold anger towards your family?

Does she tense up when you bring up her family and getting to know them?

girls love personal questions that really make them open up about their life

18. Does forgiveness happen easily for you?

Or is she a grudge holder? Be careful what you do!

19. What do you do to find inner peace?

Does she do yoga, meditation, prayer?

Or karate, kickboxing and power lifting?

20. What act makes you feel the most calm?

Walking the beach, going for a night swim, sex?

21. Do you believe that all is fair in love and war?

I mean if there wasn’t love there wouldn’t be passion, if there wasn’t war there wouldn’t be love….

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22. What is the most important thing a person can do to improve themselves?

Is it internal or external?

23. Is everybody equal despite all the differences?

Everyone can be equal even though life isn’t fair.

24. Do you believe in evolution, the bible, etc?

Did we fall from the sky? How did we get the right to be here?

25. How do you define evil? Do you think people are born that way or become that way because of their environment?

See how she defines evil, as a person a murderer or a rapist, or if she describes them as heartless and sad…

26. Which generation do you think has been the best? Are we improving as a whole or becoming worse?

Is she looking for the good or focusing on the bad?

27. What is your absolute favorite book and why?

Is it a romance novel, a thriller, a mystery, etc. What she likes she is probably looking for.

28. Why do you think it is so hard for people to connect beyond the surface?

Are people that afraid of connection even though they crave it more than anything?

29. Do you think technology has hindered society more than it has helped it?

Does she think technology is the reason for all the pain and heartbreak and depression, or does she think it’s the reason people can stay in touch with loved ones and talk with their families all over the globe?

30. What stops you from pursuing your dreams whole heartedly?

Who told her she couldn’t make it and why did she believe them?

31. Tell me about the most interesting place you have ever traveled to.

Is it because of the place or because of the person she was with? Does she take in the environment or the vibe? Or both?

32.  How do you know when you’re in love?

What is that moment like? Is it a moment or a series of moments?

33. Are relationships made to last forever or do you have multiple soulmates in this life?

Does she believe in the one or having multiple one’s?

34. Have you ever been in love with someone who didn’t love you back or vice versa?

What does the sadness look like in her eyes?

35. Have you ever been a part of a protest? If so, what did you fight for or against?

Is she passionate about the well-being of the planet?

36. Would you consider yourself spiritual or religious?

Does she believe in something greater than herself and a purpose beyond the self.

37. What is the worst thing about being in a relationship?

Do her red-flags align with yours?

38. Is being famous something you want?

Or do you want to be a hermit? Or somewhere in between?

39. What is your favorite thing about yourself? Name something physical and non-physical.

Does she pause or is she confident in knowing her redeeming qualities?

40. What is something you want to do but have never done?

Sky diving? Bungee Jumping?

41. How do you define friendship?

Someone always being there no matter when you need them…

42. How do you define healthy boundaries?

Boundaries.. this generations favorite thing to talk about.

43. What is one of your hidden talents?

Can she sing super well but is too shy to in public?

44. What is something you know how to do that most people don’t?

Can she sail, fly an airplane?

45. What is your view on pictures?

Does she love them, or does she wish to enjoy the moment? Or maybe both, capture the moment and treasure it forever.

46. Do you have an easier time holding on or letting go?

Does she battle her head and her heart?

47. What is something you think everyone takes for granted?

Nature, the way it keeps giving no matter how much we take…

48. Do you sing in the shower?

Who doesn’t?

49. How old were you when you stopped believing in Santa and the Tooth fairy?

Did she ever even believe at all?

50. What is something unusual that you think everyone should try?

A food dish or an excursion?

51. Do you believe in life on other planets?

Do the aliens speak to her from worlds away? If they do run, run the other way!

52. Do you think you are responsible for all the decisions you make?

Or is she constantly victim blaming?

53. Do you create your own reality?

Inside your head there’s a whole different reality than anyone else’s.

54. Would you rather get married in your 20’s or 30’s and why?

Does she want to explore and experiment when she’s young or settle down and have kids right away?

55. If you could jump into a pool of something what would it be?

Water… chocolate… let her get creative with this one!

56. What is your phone background and why?

Does she have a picture of herself, her family, her favorite mountains?

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57. What do you want people to say at your funeral?

Does she even want a funeral? Or does she want a giant party?

58. What do you want to be written on your tombstone?

What kind of girl she was or what kind of girl she wished to become…

59. What is the best gift someone has given you?

See her tastes so you know how to give too.

60. What is the best gift you have ever given?

Was it an adventure, or something money could buy?

61. How do you spend most of your free time?

Does she spend it on her own or with the people she loves the most?

62. Do you think the past matters in a current relationship?

Or does she think what is done is done…. nothing is ever done.

63. If money didn’t matter what would your ultimate goal in life be?

Hard one, let her think about it.

64. Tell me one secret about yourself.

Maybe she can’t because it is a secret!

65. Has anyone in your close family died? How did you deal with the death?

Has she lost a grandparent, parent, sibling? Is she still crying everyday or learning to deal with it each and every day?

66. What is the most important thing you have learned so far in life?

What’s her biggest lesson… is it about love? She’s probably a hopeless romantic. Aren’t we all?

67. Are you insecure about anything?

Who isn’t but is it physical or internal? You can help her fix both.

68. Do you prefer routine or spontaneity?

Let her get into that birth chart and describe why she is the way she is.

69. What is your fondest memory?

Maybe she’ll talk about a time far in the past or maybe it will be something with you. But, you’ll hep her make more incredible memories.

70. Do you think opposites attract?

Do they attract but never last?

71. Is honesty always the best policy?

Or are little white lies ok sometimes?

72. What is increasingly becoming socially acceptable?

Nudity, porn… see where her mind wanders to.

73. What book or movie character are you most similar to?

Does she describe a villain, a hero, the protagonist, antagonist or a supporting actress?

74. What is the best and worst thing about being female?

Ahh, how the list is never ending on both sides.

75. What part of your culture are you most proud of? Least proud of?

Most proud of the way things have progressed but least proud of the way things have at the same time remained the same…

76. How quickly do you jump to conclusions about people?

Does she wait to say anything until she’s met someone three times? Or does she let it out right away?

77. How do you view the education system?

Do teachers make enough money? Too much?

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78. Do you have regrets?

Or does every mistake teach you a lesson and make you a better person?

79. Does death frighten you?

Or is she eternally alive?

80. How do you view time?

Is she afraid of the clock running out of time, or is time a construct of the mind?

81. What makes humans and animals different from each other?

Humans can communicate unlike any other animal, duh…

82. What is your biggest flaw and your biggest strength?

Are they one in the same?

83. What is your biggest pet peeve?

Do little things really get to her or is she more of a big picture type of person?

84. What is your favorite family tradition?

Thanksgiving, Christmas…

85. What is your very first memory?

Does she even have one, or do they all sort of blur together?

86. Do you believe in reincarnation?

Or is this your one and only life? Both ideas are so beautiful.

87. What is the most embarrassing thing you have done?

I’m sure she could go on for hours about all the embarrassing things she has done.

88. What assumptions do you think people make about you?

Are they generally correct or wrong?

89. What do you wish you knew when you were younger?

Now that you’re older, what would you have told your younger self?

90. Do you wish the days were longer or shorter?

Or is she perfectly content with the days as they are? I mean you can’t change them anyways.

91. Are you a procrastinator or a go-getter?

Depending on the topic…

92. Have you ever been depressed?

Like truly unable to get out of bed and get dressed?

93. Would you consider yourself an empath?

Or a psycho? Or a little bit of both?

94. Where do you go when you are sad?

Does she go inside herself or does she seek what is external?

95. Do you journal?

Does she let all her feelings out on paper or does she have a quick tongue?

96. What is the dumbest thing you have done this week?

Lets get a nice deep laugh going with some flirty questions.

97. What makes someone a “good” person?

Is it the things they do, think, say or all of the above?

98. Can you describe your best friend to me?

That’s the best indicator about what type of person she is. How she sees the people closest to her.

99. Would you rather have infinite money or love?

Love, always love, but maybe love of money…

100.What are you most grateful for?

Does she live every moment in gratitude?

These 100 questions will answer just about every question you’ve ever had about your female friend or lover. You will get to discover the way of her mind, heart and soul.

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About the author 

Coach Colt here, the founder of Dating Armory, your go-to source for no-nonsense, practical relationship advice. I'm a bisexual male in a same-sex open relationship and a researcher in sex, love, and relationships with 7+ years of experience. I specialize in helping both men and women navigate the crazy world of dating.

Don't miss my other guides packed with practical dating advice (no bullshit repeated Platitudes) and tons of real life examples:

My Top 57 First Date Ideas That Always Work (As a Dating Coach)

Are Coffee Dates Good? It (Kinda) Depends

17 Basic Coffee Date Tips (From a Dating Coach)

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