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93 Interesting Questions to Ask a Girl – Spark engaging conversations.

Why should you know interesting questions to ask a girl?

Well… like a lot of us guys have realized:

Women, as a whole, can seem very difficult to talk to. For some of us, just getting into a conversation can be difficult.

But all we’re missing, really, are the right questions to ask. With a few interesting questions to ask a girl, you can get her to open up in surprising ways.

Even having that secret in your pocket, though, it can still feel a little hard to find your way forward. Should you be looking for some funny questions to ask or should you go more serious?

The truth is, finding the right questions to ask a girl is a bit of an art, something you feel your way through. But the best way to feel out the right question is to make sure to have a number of different types ready at hand.

And no matter what, make sure to keep them all interesting.


13 Interesting Conversation Starters to Ask a Girl

If you want to get anywhere with a girl, you need to be able to start a conversation. That’s what we have conversation starters for.

Use a few of these to get your chat going strong.

Here are 13 interesting conversation starters to ask a girl:

1. If you were on the run from the police for a crime you didn’t commit, where would you go?

One part shock, one part honest confession. You’ll find out who she really trusts in her life.

2. What’s your favorite thing about this city?

The restaurants, the art scene, maybe just a small out of the way park: no matter her answer, you’ll have an idea handy for future meet-ups or date nights.

3. How would the world change if super heroes and super villains actually existed?

Show off your nerdy comic book knowledge, and give her a chance to do the same.

4. If you could put your brain in a robot and live indefinitely, would you?

Here’s your chance to really play philosopher and drop a few fancy names and concepts.

5. Would you rather have a million dollars and live in a place you hate or struggle in the place of your dreams?

Whether she’d take the money or the dream move, it’ll let you know what her priorities are.

6. If you ruled the world, what would you change?

This question offers a chance to complain about all that’s wrong with the world and figure out how to fix it.

7. If you could have been a child prodigy, what would have been your skill?

We all wish we had some incredible, inescapable talent, but what would it be for her?

8. If you could make one rule that everyone had to follow, what rule would you make?

Discover this girl’s biggest pet peeve at the beginning of the conversation. That way you can avoid it!

9. Would you rather play a villain or a hero in a movie?

A fun way to start a conversation that can lead to an amusing talk about favorite heroes and villains.

10. What is something that is popular now that annoys you?

Give her a chance to complain about “kids today,” even if she still is one.

11. What style or habit do you wish we could revive from the past?

Men wearing fedoras? Old-school manners? The drive-in theater? What does she wish would come back into style?

12. What’s your favorite sport to watch in person?

You can use this question to invite her to see an event for herself.

13. Would you rather drink a bottle of tabasco sauce or eat a chili pepper?

This is a great way to find out if she’s up for anything, and also if she’s a fan of spicy food.

9 Best Interesting Questions to Ask a Girl

Once you have a conversation started with a girl, you’ve still got to keep it going.

Perhaps the quality you most want to leave a girl you’re talking to with is that you’re interesting. And the best way to make her see you as interesting is to keep asking interesting questions.

Use a few of these to keep the conversation going and keep it going in interesting directions.

Here are 9 best interesting questions to ask a girl:

14. What is something you used to do as a child that you wish you could still do?

We all leave hobbies and activities behind as we grow up, but what does she miss most about childhood?

15. Does your name mean anything?

Most people have looked up the etymology of their name, and it can lead to some very interesting conversations.

16. What do you know about your family’s history?

Get a story out of her about her family past. She may have a lot to say about the cultures in her background.

17. If you could go back to any age or time of your life, what age or time would it be?

Once you know the answer to this question, you have a good idea what she needs to make her happy.

18. If you could tell the you of ten years ago one thing, what would it be?

Advice from the future: what has she learned about life now that she’s lived a little more of it?

19. What can you do today that you were not capable of a year ago?

Does she work hard on self-improvement? If she does, what areas does she improve?

20. What are you freakishly good at?

You can give her a chance to show off a hidden talent and also find out something she may really enjoy but rarely get the chance to bring up.

21. What’s one thing you’re deeply proud of — but would never put on your résumé?

Use this question to learn how she defines herself away from her professional self.

22. What do you value most: free time, recognition, or money?

Perhaps the three biggest motivations in life, but what does she prioritize as most important of all?

5 Interesting Questions to Ask a Girl You Just Met

Perhaps the hardest conversation to start is the first one. Or the second or third.

Those early conversations with a girl you just met are difficult because you know so little about her, and you can’t be sure you’ve impressed her enough yet to have that next chance in the next conversation.

Use some of the interesting questions below to make sure you impress her on those early occasions, so you know there’s always a next time.

Here are 5 interesting questions to ask a girl you just met:

23. If you could only do one thing for the rest of your life, what would it be?

A great way to get to know if someone has a true passion in their lives.

24. What was your favorite getaway location as a kid?

You can learn all sorts of things about a girl by finding out about her childhood.

25. If you could trade places with anyone in the world, who would it be and why?

Finding out who she wishes she could be will tell you what sort of person she wants to be and where she sees herself in an ideal world.

26. Do you have any secret hobbies you’re passionate about?

The key here is the “secret.” She may be very public about some hobby, but what does she love to do that no one knows about?

27. Would you rather have an extra $200 a day, or an extra 2 hours a day?

Would life be better with more money or with more time to enjoy what you already have?

10 Interesting Questions to Ask a Girl to Get to Know Her

Once you’ve gotten through those first conversations, you need get to know you questions. These quickly dig a little deeper into who the girl you are talking to really is.

Having the right questions to ask a girl to get to know her won’t just get you a quick and interesting reply, they’ll lead to long and personal conversations.

It’s through these questions that you move from casual conversation acquaintances to friends, colleagues, or something more romantic.

Here are 10 interesting questions to ask a girl to get to know her:

28. What does your own personal hell look like?

Fun, imaginative, and full of interesting potential responses, this question lets you find out what bugs her and what frightens her.

29. What does your own personal heaven look like?

Find out what objects, places, foods, and relationships she considers so ideal she’d put them in her perfect place.

30. What’s on the top of your bucket list right now?

It’s another way of asking what the one thing she truly wants to experience in her life is.

31. What’s your go-to karaoke song?

A fun question that opens up further questions of tastes in music, art, and entertainment, and also a little history about why she loves to sing that one particular song.

32. What is the most unusual fear you have?

Brush past all the obvious fears (spiders, scary movies, clowns) and discover something truly unique about what scares her.

33. Is there any fairytale or movie that reminds you of your own life?

Is she a put-upon Cinderella or a Sleeping Beauty waiting for a Prince Charming? Get her to sum up her whole life up to this point.

34. What’s the most awkward to explain thing you’ve ever been caught doing?

Develop intimacy quickly by sharing a few embarrassing stories. Share a couple of yours first.

35. Who is / was your most interesting friend?

With this question get an answer to who she thinks is interesting, and how highly she prioritizes their qualities.

36. Is there anything you wouldn’t do for 10 million dollars?

How motivated is she by money? And what (if anything) does she hold as more important than money?

37. What’s the most valuable thing in your life?

Is she materialistic, sentimental, or idealistic?

12 Interesting Questions to Ask a Girl You Like

While many of the above interesting questions will work in a conversation with a girl you have romantic interest in, it’s still best to find unique questions to ask a girl you like, just to make sure the questions take the conversation where you want it to go.

Use a few of these to not just get closer but develop a more romantic edge to your conversation.

Here are 12 interesting questions to ask a girl you like:

38. What’s the best thing you could do for someone who needs cheering up?

There’s no surer way to a girl’s heart than being able to cheer her up when she’s upset.

39. What’s the most romantic book or movie ever?

Whichever stories she likes will tell you what she finds romantic in someone she dates.

40. Was your first kiss super awkward?

We all have awkward love stories in our past. This question gives you a chance to be nostalgic while also discussing locking lips.

41. Do you think your parents had / have a good relationship?

From Sigmund Freud onward, psychologists have thought our family relationships have had an impact on our romantic ones later.

42. What’s a childhood memory you have that always makes you smile when you think about it?

Bring her back to her happy childhood memories, and she’s far more likely to be drawn to you.

43. What would your parents be surprised to learn about you?

What has she done, or what does she like, that she wouldn’t tell her family about? Find out and then you’ll have a secret to share between the two of you.

44. What is something that your friends would consider “so you”?

A good way to find out how she sees herself is to find out what she thinks her friends see in her.

45. If you could plan the perfect day for yourself, what would you do?

You’re basically getting a free handout of the ideal date scenario without putting her under pressure for a date first.

46. What would you grab if your house was on fire?

What does she prize among all her possessions? Would she grab a musical instrument or her family photos?

47. What’s your favorite thing to do when you’re sick?

If you know how she pampers herself when she’s ill, you can pamper her yourself, ill or not.

48. What is your destination for the trip of your dreams?

The places she wants to go suggest the sort of person she is. Is she a party girl looking for a trip to the islands? Or is she a romantic who dreams of Paris?

49. What’s the last thing that had you so excited you couldn’t sleep?

Find out her passions and interests with this question.

10 Interesting Questions to Ask a Girl Over Text

These days, conversation increasingly doesn’t take place in person, looking at each other in the eye.

Instead, we ask our interesting questions through our technology, and that can mean we need to change our questions a little.

But fear not, once you have some questions to ask a girl over text, you can get to know her, even if it is through a screen.

Here are 10 interesting questions to ask a girl over text:

50. What’s your earliest memory of your phone?

Nowadays, our phones are with us 24/7, but that wasn’t always the case. You can take a stroll down memory lane with her to simpler times with this one.

51. What’s the worst book you’ve been forced to read in school?

Have a laugh at the expense of literature, and find out about her tastes in books.

52. What’s the funniest .gif you’ve seen lately?

This is the easiest way to get to start swapping amusing images and links to keep the conversation going.

53. What’s the strangest message you ever received?

Share a little history about odd texts or emails you’ve received, and bond over the oddity of modern communication.

54. What do you think was the “worst movie ever”?

Instead of going for the obvious favorite movies list, give her a chance to go off on the one she hates the most and learn which movies to avoid if you take her out.

55. What is the most interesting thing you have near you right now? Send me a pic of it.

The objects we keep close to us often say a lot about who we are.

56. What app on your phone do you think I should get?

If she has an app she absolutely loves right now, you’re in for quite a conversation.

57. What’s your favorite cancelled TV series?

We all hold a few short-lived shows in our hearts. Talk about yours and hers, and share some clips. Maybe you can plan a get together to rewatch all those classic episodes.

58. What’s your most impressive thing you’ve tried to cook with an online recipe?

Unless she’s a chef, she’s probably tried to google a culinary masterpiece last minute like the rest of us. Share a few stories and then invite her to dinner to try out a new recipe.

59. If you could head out on a road trip right this minute, where would you go?

Discuss potential road trips and figure out the best routes you could take to see the most interesting things. Then, if your relationship progresses, take one of the trips together.

10 Interesting Questions to Ask Your Girlfriend

A lot of the questions above focus on getting to know someone and making sure your first few conversations are interesting and allow you to get closer.

But that doesn’t mean once you’re dating someone or in a relationship you don’t need to keep asking the right questions.

In many ways, having questions to ask your girlfriend is just as important as having questions to ask a girl you want to date.

It’s crucial to the health of any relationship—new or not—that you keep things interesting. So, use a few of the questions below to keep her amused, intrigued, and focused on you.

Here are 10 interesting questions to ask your girlfriend:

60. What do you think is your best—and worst—feature?

Find out from her what she thinks is great and not so great about herself.

61. What should I know about you that I’d never think to ask about?

You’re really asking her to develop and ask herself a great question for you.

62. Do you prefer going out or staying in?

A critical question for any couple. If you know her preference, you know which to plan for more often on date nights.

63. What makes you say “What was I thinking?” when you look back on your life?

A fun discussion of regrets can lead to discoveries about her past.

64. What kind of parent would you like to be?

If you plan to stay together long-term, this will be an important topic. So start the conversation now and find out how she feels about kids and parenting.

65. What are the 3 biggest things that I could do for you?

You may assume you know what she wants from you at all times, but there may be things you never think of, and often they are smaller and easier to accomplish than you imagine.

66. Are you strangely sentimental about any objects you own?

What object does she have an attachment to that most people wouldn’t guess?

67. What would you like our shared goals to be this year?

A great way to keep your relationship strong is to set goals and meet them.

68. What are the three most annoying things a boyfriend can do?

A boyfriend keeps you in the clear from personal criticism. Use this one early in the relationship to save yourself making those mistakes later!

69. What are some unwritten rules in your family?

With this question, you’ll be more prepared to meet her parents when the moment comes.

5 Interesting, but Personal Questions To Ask A Girl

Being interesting means getting personal. You have to open up!

And having personal questions to ask doesn’t hurt when you’re at a loss of what to say.

We’ve put together a more comprehensive list of personal questions to ask a girl but wanted to show you the best of them here.

Here are 5 interesting, but personal questions to ask a girl:

70. A smell that takes you to your childhood?

Nostalgia is a powerful drug that’s nice to indulge in from time to time. Follow up with more questions about her childhood.

71. What three things do you think you have in common with me?

She might mention something you didn’t realize you have in common.

72. What do you think is too serious?

Who (or what) really needs to take a load off?

73. What was the biggest tragedy you ever had while cooking something?

Kyle’s #1 Cooking Tip: Learn the difference between a clove and a bulb of garlic.

74. Have you ever received some lavish treatment?

We can’t all live like kings but every so often we can get a whiff of what it’s like.

11 Interesting, but Deep Questions to Ask a Girl

So, you now have interesting questions for a girl you just met, a girl you’re talking to over text, girls you like, and girls you’re in a relationship with.

But what if you want questions that aren’t just interesting? What if you want questions that are deep?

Getting the right deep questions to ask a girl (or deep questions to ask your girlfriend) allows you to not just be interesting but to add a little extra substance to your conversation.

Use a few of the questions below to take your interesting conversation to the next level.

Here are 11 interesting, but deep questions to ask a girl:

75. What is one thing you always wish you’d have time for but can never find it?

This question opens up conversations about priorities and whether we can ever have enough time for everything we want.

76. Which memory has most defined you?

Memories are always precious, but to choose one that made you who you are, that requires some deep thinking.

77. What is one dream you think you’ll pursue relentlessly for the rest of your life?

Find out what it is about the dream that makes her want to define her whole life by it.

78. What would you do if you didn’t achieve your dream?

How would she recover from not achieving the dream she mentioned above? A serious question to work over how we recover from failure.

79. What is one thing you feel your life is missing?

This can be a rather existential question that takes in society, the soul, and our constant dissatisfaction with life.

80. Which is better to listen to – your heart or your head?

It’s a simple question but with complex implications. Is she impetuous or does she think before she acts?

81. What acts of kindness do you think would create the most change around the world?

Is it the big, impressive acts that make the world better or the little things?

82. If you were given an envelope with the the time and date of your death inside, would you open it?

This is sort of a Pandora’s Box question. There are so many possible implications to opening the letter or not.

83. What about love scares you?

Intimacy is scary for everyone, and it’s worth having a serious, deep conversation about what parts of that idea scares her, and you.

84. If you could fix your biggest mistake in life but only if you gave up your biggest accomplishment, would you do it?

Are your regrets great enough it’d be worth losing out on the best thing you’ve done with your life? Here’s a chance to make that bargain.

85. Would you rather be with someone who occasionally tells big lies, or someone who is brutally honest all of the time?

There’s no right answer to whether a few lies or tough truth is the way to live life, but you should both try to come to the same answer.

8 Interesting and Weird Questions to Ask a Girl

What do you do when you want some weird questions to ask but you want the conversation to evolve into something a little more interesting? Combine the two with the interesting, weird questions you’ll find here.

These weird questions to ask a girl will give you that out of left field appeal but also lead to the most interesting chats you’ll have all week, which is great news if you want her coming back for more soon.

Here are 8 interesting and weird questions to ask a girl:

86. Define marriage in a sentence.

She’s only got one, so you know whatever she comes up with, it’s definitive.

87. What would you rather have – a million dollars, or 20 years of complete unconditional happiness?

Find out where she falls on the “money can’t buy you happiness” vs “yes it can” debate.

88. Do you believe in the existence of Aliens?

Talk about the stars, the potential for communication, and what it would mean to no longer be alone in the universe.

89. What are the two most important things in your life and why?

If you get her to answer honestly, you’ll know her in the two things she lists.

90. Have you ever been inside a gents toilet?

If it’s a yes, get the story. If not, give her the low down on the best and worst you’ve seen.

91. Is there anything that you would never want me to know about you?

She’s stuck with this one, and she may just reveal something incredible she was keeping hidden.

92. Would you give a homeless person CPR if they were dying?

A tough ethical question that will tell you a lot about her.

93. Do you like spicy food and why?

No matter her answer, this is a great opening to offer to take her out to your favorite restaurant with a bit of spice.

How to Ask a Girl Interesting Questions

A list of questions is no good if you aren’t sure how to go about asking the questions in the first place.

Even if you’ve got a great question in hand, it can seem like the hardest task in the world getting the words out.

To make it easier to just come out and ask, follow these five steps.

Here is how to ask a girl interesting questions:

1. Decide Who You Want This Girl to Be

The first thing to think about when you are trying to ask a girl interesting questions is what kind of relationship you want with this particular girl.

Are you looking for something romantic? A friend? Is she a work colleague or a boss? Or is she just a girl on the bus you’d like a chance to get to know her a little better?

The tone of your conversation and your choice in question will change depending on who you’re talking to.

2. Pick the Right Place

Once you know who this girl is to you and who you want her to be, you can start thinking about finding the right place to ask your questions.

Say you want to chat with your boss more. You may want to find a place that is inviting but still relatively business-focused. Whereas for a potential friend the place should be completely casual.

Keep in mind, the place should partly frame your questions. Ask questions that relate to the place you are. If you’re at a bar, talk about music and drinks. If you’re in a park, talk about nature.

3. Pick the Right Moment

Similar to the point above, make sure the moment is right. Pick the moment that most allows both you and the girl you’re talking to to be comfortable and prepared to spend some time talking.

If you’re talking to a girl you like, pick a moment when she seems relaxed and open to conversation. She’s much more likely to be receptive to what you have to say then.

4. Pick the Right Question

Obviously, you need to make sure your question fits the person, the place, and the moment.

If you’re in a bar trying to talk to a cute girl, for instance, don’t immediately launch into questions about her past or her plans to have kids. Instead, choose a fun question that might make her laugh.

Getting the question right is the best way to take any conversation and direct it to where you want it to go, and to turn relationships into the sort you want them to be.

5. Be Confident and Keep a lot of Backups

The best way to get a good answer to your questions is to be confident when you ask, and be prepared for some questions to fall short of expectations.

You can’t always control if a question is going to be a hit, but don’t get discouraged. The best thing to do in such a situation is to laugh off the flop question and throw another one out there.

The more questions you have, the more likely you’ll be able to find the right one that really gets her thinking.

Downloadable and Printable List of Interesting Questions To Ask A Girl

Here is a downloadable and printable jpg/pdf list of interesting questions to ask a girl (right click the image and select Save Image As…):

More Interesting Questions to Ask a Girl

We’ve covered a lot in this post, but if you are still looking for more interesting questions to ask a girl (or someone else), there’s not need to fret. We’ve got plenty more options for you.

  1. A lot of our questions to ask a guy would also be really interesting to ask a girl.
  2. However, if it isn’t about guys or girls just getting great questions that really make you think, then head over to our philosophical questions/existential questions article and take a deep dive into the questions that keep the great minds up at night.
  3. And, if you want something that can surprise a girl and will definitely get a reaction, take a look at our random questions to ask a girl.

In Conclusion

No matter where you are in relation to the girls in your life—a partner, a friend, a coworker, an acquaintance, or a complete stranger—you need to have questions to ask ready to ask in order to build those relationships.

And using interesting questions to ask a girl is the most direct way you can find out what you want to know about any girl. Whether you want deep answers and greater intimacy or just a casual chat that gets you past introductions, questions are the way to do it.

Remember, no matter what you want to know about a girl, all you have to do is ask (the right questions).

About The Author


Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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