96 Deep Questions to Ask a Girl – Spark deep, personal conversations.
New? Start here. | This post contains affiliate links. That means that we receive a commission for purchases made on them (more info).
Asking deep questions to ask a girl is a quick way to build a deep relationship.
…And as any guy who has been in one before knows:
Deep relationships are truly satisfying.
While some of these might be easy to ask your best friend after a few too many beers, today we’re going to be focusing on deep questions to ask a girl to cultivate a deeper relationship.
Anything that is experienced by most people gives a great opportunity to deepen a conversation with a girl. Of these, there are three conversation topics that stand out most to me are love, loss, and happiness. Because of the universality of these experiences, they are a definite way to find common ground on deep conversation topics.
Here are 3 great deep conversation topics to use with a girl:
Happiness is the easiest choice to begin with. Every time we think of a happy memory, a good time in our life, our brain sends signals to relax and open up. Start by asking: What is it that makes you happy? Then, how does this relate to what makes the girl you’re talking to happy? Finding common ground on shared sources of happiness creates a road for deeper connections.
Loss is a fact of life, no matter how painful it may be. Being able to be there for someone when they’re experiencing pain — whether right now, or only in their memories — creates a depth of connection beyond just talking about what makes you happy.
#3: Love/what she defines as love
Love might be the hardest to talk about, but most rewarding of all three topics. Who, or what, do you love? More importantly, how is it that each of you defines love — what does it mean to you to love someone (or something)? Though the experience of love is shared by people everywhere, our opinions on what it means, and how and where we find it, can differ significantly.
These deep conversation starters should be your go-to questions to break the ice. They offer a glimpse into the depths of the girl you’re talking too, without being too heavy-handed to get started with. Take a little time to introduce yourself and share some basic information, then pick one of these conversation starters to get the ball rolling towards deeper topics.
Here are 17 deep conversation starters guaranteed to get you off to a good start:
1. How did you meet your best friend?
The friends a person keeps shows a lot about their character.
2. What’s on your bucket list this year?
What is it that each of you is searching for in life? Having shared goals in life that you’re both working towards is a great way to develop a deeper connection with a girl.
3. Do you think alien life exists?
Being open to the unknown is a good sign of humility and openness — both traits that lead to deeper connection.
4. What is the next big thing you want to accomplish?
People with goals that they’re willing to work for are happier, healthier, and more comfortable in deep relationships.
5. Do you prefer having a lot of friends or just a few close ones?
Lots of friends usually means more superficial relationships, whereas with a few close friends, it’s easier to share a deeper connection.
6. What were some of the best and worst things about where you grew up?
Bonding over childhood memories is a great way to get to know someone got to where they are today.
7. What one thing would you change if you had to do it over?
How much is she willing to talk about? Everybody has regrets, but not everyone will want to talk about them right away.
8. If could choose only one long-term goal, either to own a house or to travel the world, which would you choose?
Whether your heart is set for the open road or to have any talent in the world, what would it be?
9. What do you wish you had more time for?
One of the best deep conversation starters, this one can show what a girl prioritizes in her life.
10. If you had to leave our country for good, where would you go?
Every country offers a different lifestyle. Do your choices match up?
11. If you could trade 1 year of your life for $100,000, how many years would you trade in?
How much do you value your life? Time may be the most valuable thing we have.
12. What is something that everyone should everyone be trained to be able to do?
CPR? Knitting a sweater? Posting on Instagram? Each answer shows a different level of depth of character.
13. If you had the superpower to slow down time, what would you do?
What would you do with more of our most valuable resource? Whether mundane or extraordinary, this one tells what a girl finds most valuable.
14. If you didn’t have to worry about money, what would you do all day?
Following your dreams is a game of balance: If money weren’t part of that equation, what would be more important?
15. If you had a past life, who do you think you would have been in that life?
16. What do you think the secret to a good life is?
Or, is there a secret at all?
17. Do you believe things happen for a reason?
A question with a spiritual and philosophical bent. Are you both able to find value in everyday occurrences?
After you’ve taken the time to start into a deep conversation, paying attention to what both of you are sharing along the way, it’s time to use some of your best deep questions to keep the momentum going. Easy does it with these: They can be cause for really deep thought, so don’t try to rush any answers.
These are 17 of the best deep questions to ask a girl:
18. In what order would you prioritize these four: money, love, career, happiness?
Being able to match up your priorities is a definite sign of compatibility.
19. What’s one thing you wish you could do differently in your life so far?
Can she learn from her mistakes? Doing so is a huge part of growing up and connecting with others.
20. How have your strengths helped you to succeed?
Let’s face it: Self-confidence is one of the most attractive traits for someone of the opposite sex to have.
21. How have your faults hindered you from success?
…But so is being humble about your own weaknesses! (See the previous question)
22. What is one mistake that you will never do again?
And can she learn from her mistakes? Being able to start again after a failure is a trait many of us share.
23. Do you want to be famous? If so, what for?
Fame and fortune aren’t always what they’re cracked up to be, but wanting to be recognized is a sign of healthy self-esteem.
24. What would you do if you had only 1 day left to live?
I.e., what is most important to you? Family, friends, and adventure are common responses.
25. Where do you want to be in 5 years from now?
Home in the Bahamas? Job in the corner office? Having goals for the future leads to happier, healthier lives.
26. Are there any laws that you completely ignore?
Is she a bit of a rebel? Jaywalking doesn’t count, by the way!
27. If you could retire anywhere in the world, where would it be? Why?
Where a person would like to live is a great indicator of how they would like to live.
28. If you found out your current life has been just a dream, would you choose to wake up?
Ah, the “Matrix” question. At its heart, this asks: Is it good enough to live in a fantasy world, or do you crave an understanding of reality?
29. What belief do you have that most people disagree with?
Being willing to stand up for your beliefs in the face of adversity shows how a person stays true to themselves.
30. Do you believe in the idea of karma?
And with that, does she take responsibility for her own actions?
31. What one, single word do you hope that people use to describe you?
Being aware of the way other people see us, and how we want to be seen, can be a healthy way to make lasting connections.
32. What is the most important thing you have learned in life?
Sharing similar lessons in life can give you a way to connect with where you’re at right now.
33. What is your best childhood memory?
The way a person was raised has a huge effect on their satisfaction with life as an adult.
34. If your house was on fire and you could save one possession, what would you save?
What is most important to you both? And do your priorities match up?
Man or woman, everybody enjoys talking about themselves. All of these questions to ask to get to know someone are especially useful for letting the girl you’re talking to be the center of attention for a while. As always, listen closely to these — the details she’s sharing can tell you a lot about her.
Here are 20 questions to ask a girl to get to know her better:
35. What’s the coolest thing you’ve ever done?
Bungee jumping? Traveling the world? Everyone has something from their life to brag about!
36. Is it better to have loved and lost than never to have loved at all?
Tennyson had it right: We learn the most from the lessons of lost love.
37. What’s one realistic thing the government could do to improve the lives of its citizens?
A gentle introduction to politics, this one opens the door to a deeper discussion of how we can all work together to make the world a better place.
38. If you could describe yourself in one word, what would it be?
Essentially, how does the girl you’re talking to want the world to see her?
39. Do you feel you have a purpose or a mission in life?
This is one of my favorite questions to ask a girl to get to know her. People who are driven by a purpose or mission are always more likely to succeed in their lives!
40. What is most likely to bring about the extinction of the human race?
Popular answers include “zombies” or “global warming“. Which side are you on?
41. What’s your biggest dream?
Our dreams can keep us going — even during hard times, it’s darkest before the dawn.
42. Are you close to your family? What’re they like?
Our relationships with our family define a lot of our ability to connect deeply with others; a healthy family life is a great sign.
43. What about yourself do you find the most pride in?
To connect deeply with others, we must first have healthy self-esteem — something about ourselves to be proud of.
44. What personality trait do you wish you had?
And how can you develop that? Nobody’s perfect, but having goals for how we act is a big plus.
45. Have you ever had your heart broken?
Connecting empathetically on this common experience helps both parties to feel more connected, and safer around each other.
46. What do you think the world will be like in 20 years?
Optimist, pessimist, or realist? A girl’s outlook on life says a lot about how successful she’s likely to be.
47. Who is your biggest influence in life?
Staying connected to the people in our past helps prepare us to walk boldly into a happier future.
48. What are you grateful for in life?
Gratitude is a key player in the search for happiness and connection in life.
49. What job do you think you were born to do?
And if you’re not doing the job you think you were born to do, what is it that’s stopping you from that?
50. What do you hope you grow out of?
Can she be comfortable with the process of growing up, and even take an active part in it?
51. How much do you judge a person by their appearance?
Is she looking for beauty on the outside, or the inside? Deep connection needs the latter.
52. What was the worst phase you’ve gone through in your life?
The hard times, and our reactions to them, help define us as people.
53. What type of old person/grandparent do you want to be?
Life isn’t only great when you’re young. How cool does she want to be as a senior, too?
54. What part of your life would you like to simplify?
We can’t do everything, all the time — sometimes you have to make choices to simplify.
Once you’re in a relationship, a whole range of new questions to ask your girlfriend opens up.
Here are 12 great deep questions to ask your girlfriend:
55. Would you rather be traveling the world, or building a home?
The two of you will need to learn to balance stability and adventure to keep your relationship exciting.
56. How can we support each other in hard times?
It’s better to have this conversation during brighter times in your life, so you’ll be prepared for any challenges together.
57. Would you want to raise kids in the neighborhood you live in now?
There’s a perfect place in the world for everyone; are you living there now?
58. What quality of yours are you most proud of?
It’s good to have deep questions that turn the focus positive, as well — this one helps to show what’s truly special about your girlfriend.
59. What part of our personalities would you most like to improve?
Being able to be honest about your faults helps build healthier relationships.
60. How important to you is time spent alone?
Knowing how much space each person needs in the relationship helps prevent unnecessary arguments.
61. What do you appreciate most about our relationship?
Too many couples don’t take a moment to show gratitude for how their relationship benefits their lives.
62. What does a perfect day spent together look like to you?
And then, how can you take steps closer towards that perfect day together?
63. What’s the most important thing for us to work on together right now?
Successful couples share common goals; it’s worthwhile to talk about this one at length to get on the same page.
64. Which is more important: Success, or happiness?
Being successful might make you happy — but does being happy make you successful?
65. What song would you choose to represent our relationship?
Music speak straight to the heart, and can communicate difficult or complicated emotional states.
66. Are “white lies” okay?
Do you two have total honesty in your relationship, or are there gray areas?
Keep a few of these philosophical questions in your back pocket for those times that the conversation takes a very intellectual turn. Be cautious, though: They’re best used sparingly, as they can tend to dominate a conversation for too long if left unchecked.
Here are 3 thought-provoking, philosophical questions to ask a girl:
67. What is the purpose of art in society?
A person who values art is someone who’s able to see the beauty in life.
68. What is true happiness?
Finding things that make both of you happy (and then acting on them) is a sure way to make a deeper connection.
69. If we could live forever, would life be meaningless (or less meaningful)?
Maybe one of my favorite philosophical questions to ask: It shows whether she’s at peace with the cycles of life.
What makes you like a girl, other than how she looks? You like her personality, how she makes you feel, but you also like what you think you see inside her, the deeper stuff.
To get to that deeper stuff, you need the right questions to ask a girl you like. Use some of these below to get beyond the surface topics of everyday chats and start seeing who she truly is.
Here are 16 deep questions to ask a girl you like:
70. If you could relive the last year, would you change any decisions you made? If you would, which ones?
A question about recent regrets that lets you know where she’s made mistakes, and where she wishes she was in her life.
71. If you could have complete knowledge of any 5 topics, what would you want to know?
What does she wish she could truly know? And why?
72. If you got to choose between fifty years of being incredibly happy or to live forever and be unhappy what would you choose?
Is it about the time or the quality of the time we have?
73. Would you rather end all wars or world hunger?
A difficult choice, but one that lets you both discuss where most of the suffering in the world is coming from.
74. If you had a week to live and could do any 5 things in the world, what would they be?
She’ll lay out for you the five things (or people) most important to her in her whole life.
75. If you could travel 50 years into the future, but never return, would you do it?
This question covers not just the future but how adventurous she is.
76. Would you rather know a lot about a little, or a little about a lot?
Does she wish she was a trivia master or a true expert, even if it is in a very small subject?
77. Would you rather follow your dreams but never fall in love or fall in love but have no ambition or life goals?
A great question that gets to the bottom of what she thinks is most important in life.
78. What was your dream when you were younger, has it come true?
Where did she want life to go when she was young, and is she disappointed?
79. What characteristics do you most admire?
You can learn what she looks for most in people and also whether you have any of the qualities.
80. What is your biggest fear and what would be the first step to overcoming it?
Does she face her fears or run from them? More importantly, how can you help her face the next one?
81. How will today matter in five years from now?
A “seize the day” question that might lead to really making today worth remembering, with you.
82. If I could grant you one wish what would you wish for?
Is it personal? Is it global? Or is it something simple?
83. What are three moral rules you will never break?
We all have lines we won’t cross, find out hers and find out why she drew the lines there.
84. How do you find the strength to do what you know in your heart is right?
We all need strength to become better people. You’re asking if she has that strength within her.
85. What is the most important thing you do right now in your personal life?
By asking about activities she actually does, you find out what she actually, really does care about.
The deepest of deep questions are deep and personal questions to ask a girl.
Because personal questions do exactly as advertised and deal with difficult-to-talk-about subjects.
If you want to know someone on a more personal level, having personal questions to ask is key.
Check out the best of both worlds below!
Here are 5 deep and personal questions to ask a girl:
86. What do you find hilarious but most people don’t find funny?
Some people have lines they refuse to cross. Others cross as many as possible.
87. For which reasons do you most often judge people?
We all judge other people for our own reasons (not always in a negative light though!)
88. What is your favorite thing to stop and why?
If you think about this one too hard, it becomes a philosophical question.
89. How good you make people smile when they are in sad?
You won’t always succeed in cheering someone up but it never hurts to try.
90. What is the major difference between love and affection?
Everyone defines love a little differently. This question helps you understand her views on it.
Girls like guys with emotional and intellectual depth. If you really want to charm her, you need to go big. These thought provoking questions show her that you’re a multilayered catch, and they also help you to get to know her on a deeper level.
Before you get too heavy with these questions, make sure the mood is right. You don’t want to scare her off by going too big too fast. Once she’s started warming up to you, drop one of these questions and see how she responds.
Some women aren’t comfortable getting too in-depth too fast, and there’s nothing wrong with that. If she doesn’t dive right into the conversation with you, that doesn’t mean that she’s not intelligent or that she’s not into you. Sometimes, it just takes time for a person to fully open up to you.
Here are 6 of the best deep and thought provoking questions to ask a girl:
91. Are some people’s lives worth more than others? Why or why not?
Is the CEO in the high-rise equal to the junkie under the bridge? Why or why not?
92. Do you believe war can be ever be ended completely or is it inevitable that wars will continue?
Will civilization ever be truly at peace?
93. Would you take a vacation away from all technology? For how long?
Connecting with nature can be good for the mind, but it can also be a challenge.
94. Are humans getting better through the generations?
Or are we swirling through a downward spiral?
95. Is life better now than in the past?
Are we moving forward or falling behind?
96. If you had a friend who spoke to and treated you the same way you speak to and treat yourself, would you remain friends?
This question can really lead to self-reflection and introspection.
Rule #1: Start Slow
You have to crawl before you can walk, and walk before you can run. Starting out a conversation with questions that are too deep is a surefire way to lose any sort of potential connection.
Rule #2: Ask the Right Questions, at the Right Time
To reiterate from #1, because it’s so important: break the ice with a conversation starter before moving into the other deep questions to ask a girl, the ones whose answers are most important to you on a personal level. If you’re getting a good feeling after the initial question, share a little more about yourself before getting into the deeper stuff.
Once you can feel a connection starting to develop, feel free to move into the deepest end of questions: questions about love, loss, and happiness.
Rule #3: Listen
After you’ve spent some amount of time getting to know a girl through a conversation with deep questions, there may be a moment where she really begins to open up to you. This is our cue to listen!
Really listen, don’t just wait for your turn to talk again. Everything that you understand from what she says in response to your questions can bring the two of you a little bit closer.
Rule #4: Be Mindful of Reactions to Your Questions
During the conversation, look for subtle reactions, especially changes in body language.
Though most girls are polite enough not to outright tell you to stop asking deep questions, signs like her moving farther away or not looking in your direction are clear indicators that it might be time to dial it back to simpler conversation topics for a while.
Rule #5: Share
Part of building a deeper relationship is to share your own thoughts and feelings honestly.
If you spend all of your time asking questions and listening, it can begin to feel like too much of an interview for her. Instead, wait until you’ve heard her answers to your questions, then respond by sharing how your own views relate to hers.
Downloadable List of Deep Questions To Ask A Girl
Here is a downloadable list of deep questions to ask a girl (right click the image and select Save Image As…):
More Good Questions to Get to Know a Girl
If this set of questions isn’t good enough for you, we’ve got more just a click away that might help you get to know a girl even more. Give these a try:
- If she’s the sort of girl who would enjoy a crazy, less logical round of questions, try a few of our random questions to ask a girl on her.
- If you’re struggling to keep her entertained and prove you’re worth paying attention to, what you need are our interesting questions to ask a girl.
- If, on the other hand, you’ve really hit it off and moved into the relationship zone, transition over to our questions to ask your girlfriend.
- If you have thoughts of making this girl your special someone, you need some questions to ask a girl you like.
- Already in a relationship? Having deep questions to ask your girlfriend can help keep your connection strong and vibrant.
- If it’s a more casual conversation you’re looking for, it’s better to have interesting questions to ask a girl than deep ones; save the depth for when you’re ready to make a stronger connection.
There’s our 96 powerfully deep questions to ask a girl.
And whether you’re looking for questions to ask a girl to start a conversation, or deep questions to ask to make a stronger connection, keep some of these in mind. Rehearsing a few of them, out loud, until they begin to sound natural is a great way to start!
That way, when the right time comes, you’ll already know the right questions to ask. Once you get the hang of a few of the basics, try practicing with variations to really make them your own. Best of luck out there!