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Questions to ask a girl

Looking to get to know a woman a little bit better or need some questions for a woman you’ve known a long time? Tired of the same old small talk questions? We’re here to help with a list of interesting and engaging questions to ask a girl. These aren’t your normal run of the mill questions and some can actually get quite deep or a bit silly and off the wall.

These 350 questions will definitely get an interesting conversation going. You can pick and choose the ones you like or you can just ask them all. I added a bit of commentary about how to use each question and some possible ways to take the conversation. You can read through the commentary or just skip it. Your choice.

After these 350 questions to ask a girl, if you still need more we’ve got you covered:

These questions are great as stand alone questions to ask a girl, but for a really great conversation you’ll want to ask her plenty of follow up questions. And try to keep the questions open-ended. If you’d prefer an image or PDF of our first 50 questions to ask a girl we’ve got that at the bottom of the page.

List of questions to ask a girl

This first list of questions to ask a girl is a great place to start. Each question has some commentary that might help with the questions but feel free to ignore the commentary if you want. There’s also many more excellent questions to ask a girl without commentary below the first set.

So without further ado, here are our best list of unique questions to ask a woman to get to know her better.

1. Where is the last place you would ever go?

No telling what she’ll come up with for this question. You can get pretty creative with it or you can answer it literally. Either way, it’ll probably require a bit of thought but could lead a really great answer.

2. What are you completely over and done with?

So with this question there really isn’t any way to predict what she’ll say, because there are so many different ways this question can go. She might talk about a current fad or fashion, she might talk about a friend, really it could be anything.

But whatever she chooses to talk about, we all love talking about things that annoy us and she will too!

3. What memory do you just keep going back to?

Perfect for getting to know a little bit more about her. Whether it’s a serious memory or just one of those passing things that sticks with us sometimes, either way it’s a great window into her world.

Just a heads up though, this one can get real serious in a hurry depending on what memory she decides to share.

4. What’s the most immature thing your parents do?

It doesn’t really matter how old someone is, they still do immature things. Sometimes those things are silly and fun, sometimes they are more selfish or hurtful.

Either way, this is a question that she’s probably never been asked before and can lead to some really interesting answers!

5. What is the most unusual fear you have?

A question that can get really funny or really weird. Either way it’s a fun question that people generally like answering. Who knows, you may share an unusual fear!

6. What is your favorite TV show?

Sure this one is a really common question, but it’s great because if you are into the show too you have a ton to talk about. And if you haven’t seen it, now you have a good show to watch. Plus, if you don’t know anything about it she’ll probably enjoy telling you about it.

7. What’s the most ridiculous argument you’ve had?

I can almost guarantee this one will lead to a funny story. One that she will enjoy telling and you’ll enjoy listening to. I’m sure you both have plenty of ridiculous argument stories, especially if you have siblings.

8. What do you wish people would stop asking you?

At every stage of life, you hear questions over and over again. Whether it’s questions about your future, questions about life circumstances, or questions about personal things. Everyone gets asked the same questions over and over again.

9. What’s the biggest lesson life has taught you?

More of a serious question but it can be a really good beginning to a conversation. Plus, you’ll learn more about what makes her who she is and why she is the way she is now.

10. What is increasingly becoming socially acceptable?

You might learn some about what movements she supports or doesn’t support. But really this question is more about starting an interesting conversation about society.

Just remember, it’s okay that people have different viewpoints than you. This isn’t a debate. You aren’t trying to convince her you are right.

11. What pictures or paintings have had a big impact on you?

This is also one she probably hasn’t been asked before and she might have never thought about it. But I can almost guarantee that examples will leap to her mind when you ask her the question. This is question is pretty cool because you can pull up the pictures / painting up on your phone. You’ll probably get to see some cool pictures you’ve never seen.

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

If nothing else, this question will tell you how she views herself or who she wants to be more like. Always good to know, and a lot fun think about as well. There is a reason those quizzes are so popular on social media.

You could split the question into two parts, which character do you wish you could be more like and which do you think you are actually like. Or move the conversation into what books and movies she is into. You could also talk about which characters are the most interesting or unique.

13. What part of your culture are you most and least proud of?

Our culture makes up a large part of who we are and she is no different. This one can get a bit deep but it’s definitely fertile ground for a good conversation. So dive in on cultural matters and see where you both have similar viewpoints and where you differ. There will be lots of chances for follow up questions. Just remember, listen and ask questions; don’t just think of the next thing you are going to say.

14. What’s the worst and best thing about being female?

A great question that she is sure to have plenty to say about. If you are severely grossed out by feminine body stuff you might be tempted to give it a pass. But who knows, you might actually learn some stuff you didn’t know. And plus they have to live with a bunch of pain in the ass stuff that goes on with their body, the least we can do is to learn a bit about it and be thankful we don’t have to deal with it (I’m assuming you are a guy reading this, but I could be wrong).

Lots of chances for follow up questions to learn more, but yeah if it’s about bodily stuff you might not want to pry too much. But the good stuff about being a woman is great to ask questions about. You can also talk about what’s good about being a guy.

15. What random stranger has had the biggest impact on your life?

This is one that she’ll probably have to take some time to think about, because it’s not a common question. But it can be a lot of fun to answer and can be quite thought provoking as well. Plus, she’ll get to tell a story about her past and how it affects who she is today; which is always good to know.

To keep the conversation going; remember to ask more details about her story, ask about other random strangers that had an impact on her life, or tell her about a random stranger that had a big impact on your life.

16. What achievement are you proud of but most people would consider silly or weird?

This question is a great way to find out more about who she really is and what she finds interesting / fun. If the girl you are talking to is a girlfriend you might be able to use that info to create a game / competition that only you and she plays or it might turn out to be great for future gift ideas. However she answers this question, you’ll probably learn something new and interesting about her. Don’t forget to ask a lot about the details.

17. What period in history had the best fashion?

History of fashion

Not all girls are into fashion, but a fair number of them are. Even if she isn’t way into fashion, she still might like this question. It’s probably something she has an opinion on, but I can almost guarantee no one has ever asked her. To expand the conversation, you might want to ask about if different time periods were better for different genders.

18. What silly or funny thing makes you afraid or creeps you out?

This is a fun question that doesn’t quite delve into deep fears, but can still get strong reaction. You can talk about why the thing creeps her out and if she has any funny stories about the thing she is afraid of. You could also move the topic into more serious fears if you wanted to get a bit deeper. But feel free to keep it light and talk about humorous fears.

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

This one is a great question to find out more about how she views other people and what stereotypes she has. To further the conversation, you can ask her about what she thought of you the first time she saw or met you. Or you can ask her about what the telltale signs for a good and bad person are.

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

This is a question to get the creative juices flowing and I’m sure you both can come up with some funny and interesting situations that would arise if super heroes / villains existed. Sure, the girl you are talking to might not be too into this question if they don’t like comics or watching super hero movies. But with how popular super hero movies are, it’s probably a safe bet she’ll enjoy this question. If she doesn’t like those types of movies though, you might want to give this one a pass.

21. What would be your strategy for surviving an apocalyptic epidemic?

Another one that is a bit off the wall, but I’m sure we’ve all thought about it. Especially with how popular post apocalyptic shows, movies, and books are. This one is an easy one to expand into a long conversation, because you can discuss the merits of each strategy compared with each scenario. I mean, there have literally been books written about this. So yeah, lots to talk about. Especially if you two are into the post apocalyptic genre.

22. What is the most important change that should be made to your country’s education system?

This one is a bit more serious. But you can see how much she is into social change and probably get a good idea of her political leanings. Or you might find that she doesn’t really care about it. Either way it’s good intel. You can easily expand this question by bouncing different ideas off of each other and talking about the merits of each idea.

23. What is something you think you will regret in the future not starting now and what is something you already regret not starting sooner?

Oh procrastination. Yep, we all do it. This will let you know how much she procrastinates as well as letting you know about what some of her goals are and what she finds important. Try not to nag her about her answers, because one, she probably already feels bad about it and two, you probably have stuff that you should’ve already started. If your goals line up, it’s a great way to get a conversation going about what you both would like to accomplish in the future. Also, it’s great opportunity to complain about how busy the present is.

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

A couple of large philosophical questions wrapped up in a fun hypothetical question. You could talk about what makes a human a human. Or you could chat about the merits and drawbacks of living indefinitely. Or you could just talk about how cool it would be to have robot body decked out with lasers *pew* *pew*!

Baddass robot with frigin lasers pew pew

25. If you could replace the handshake as a greeting, what interesting new greeting would you replace it with?

This is a rather silly question, but it can be a lot of fun. Plus it’s doubly hilarious when you both try out different greetings. Try out secret hand shakes or high fives with elbows, you are only limited by your creativity.

26. Who’s the worst guest you’ve had in your house and what did they do?

This is usually good for a funny story. And she’ll enjoy it because it gives her the chance to break out one of her good stories. Encourage lots of details and ask lots of questions.

27. When does time pass fastest for you and when does it pass the slowest?

What does she enjoy and what bores her? If you don’t know, well now you’ll know! For follow up questions you can ask about more examples or you can prompt her with activities to see which ones she finds tedious and which ones make time fly by.

28. What always sounds like a good idea at the time but rarely is?

This is just a fun mental exercise in coming up with humorous / true examples. And I can almost guarantee there are some good stories about bad decisions to be had from both of you. See what you can come up with and see who has the craziest stories.

29. Are humans fundamentally different than animals? If so, what makes us different?

Whoa, what is this serious question doing here? Yep, be prepared for a conversation filled with landmines like religion and other strongly held beliefs. This question is not one to be busted out lightly, so pick the right time or just skip it. Nothing wrong with keeping a conversation light but I’ve always enjoyed a good deep conversation as well. So dive in or give it a pass, it’s up to you.

30. You can broadcast one sentence to every TV channel and radio in the world and have it translated to each country’s language. What sentence do you say?

A question that just begs for creativity. You can think of a lot of sentences that would have a lot of effects. You can take it in a more humorous direction, get serious with it, or a bit of both. However she wants to answer the question, remember to always ask why and find out more. Think of some more examples and try to think of what sentence would have the most impact or have the funniest outcome.

31. What fact are you really surprised that more people don’t know about?

Hey who doesn’t love learning new facts? Try to think of facts that the other person doesn’t know. You’ll learn something new and have some fun tidbits to talk about. Just remember to talk about each fact and not just fire off facts rapid fire.

32. What are you most passionate about and what do you wish you were more passionate about?

I love this question because it gets to the heart of who a person is or at least how they see themselves. You can see what actually interests her versus what person she wishes she could be. This one might even give you a glimpse into the direction she wants to take her life in.

33. What’s the best comeback you’ve ever heard?

Great comeback!

A really fun and often funny question. Chances are she has a pretty good story about an amazing comeback. Plus, you can tell any comeback stories you know. I mean, who doesn’t like hearing about a great comeback?

34. Who haven’t you seen or talked to in a long time and hope they are doing okay?

Another question that delves a little into the past. Perfect for getting to know her a little better. Get ready for a little reminiscing. Sure it’s probably no one you know, but it’s someone who is or was important to her.

35. What’s something that you’ve never been able to do well?

Sharing faults and shortcomings can be a great way for two people to become closer. Just make sure to be supportive and don’t make fun of what she can’t do, that kind of ruins the point of the whole question.

36. Who is the most humble person you know?

Kind of a random question but it might give you some insight into the people she chooses to surround herself with or the people she looks up to.

37. What is the silliest reason someone you’ve known has completely lost it?

Another one of those questions for pulling out a good story. I’m sure you’ve got a funny story about someone losing it to share as well. Great for a laugh and for getting a conversation going.

38. What is quite possibly the most annoying thing ever?

We all get annoyed at things, now you can see what she finds annoying. Probably a good idea to try and avoid doing the things she finds annoying. And there’s a good chance that you’ll both share something that you find annoying and it’s always good finding things in common.

39. What’s the weirdest tradition your family has?

Awkward family photo

I’ve come to the belief that no family is totally normal. There are weird traditions and customs in every family. Often people don’t even know that other families do or don’t do a certain ritual or tradition.

That’s why this is a perfect question for finding out more about her family and how she grew up as well as sharing some about your family.

40. If you could choose anyone living or dead, who would you choose to lead our country?

Possibly political but this one will probably end up getting more of a creative answer. It can tell you a lot about what direction she’d like the country to head in or it might let you know that she isn’t into politics.

41. What app on your phone do you wish you used more?

A little different spin on the normal “what’s your favorite / most used app” question. We’ve all got apps on our phones (usually self-improvement / education apps) that we mean to start using but never get around to.

Also this question is a great gateway question for a discussion about apps.

42. Who was the most power mad person you’ve met?

Kind of an odd question, I debated whether to include it on this list. But it might lead to an interesting story, so I decided to leave it in.

Feel free to skip this one if you aren’t into it or don’t think she’ll find it interesting.

43. What world famous monument do you have no interest in visiting?

A pretty random question, but great for seeing what she isn’t into. It can definitely lead to some interesting answers and you’ll learn a lot more about how much she likes / dislikes travel.

44. What is something that you think people are only pretending to like or are deluding themselves into liking?

A perfect question for finding out what trends or fads she just doesn’t see the point in. Definitely not a normally asked question but it can get some really interesting answers.

45. What joke went way too far?

This one can get dark quick depending on what story she decides to tell. Just a heads up. Still a great question though and can lead to an interesting story.

46. What are some of the telltale signs that a guy is creepy?

So we all know people that seem a bit creepy. So, what mannerisms makes them seem creepy? Are they really creepy or just a little socially awkward? This can really lead to a great conversation about how humans view each other.

47. What is your very first memory?

A little question that probably won’t tell you much about her, but it’s still a fun question to answer. We all like talking about ourselves after all.

48. What’s the most embarrassing thing you’ve said or done around someone you had a crush on?

Get ready for some cringing. She might not want to let you know, but if she does it can be a really good question for bringing out a good story. You might want to skip this one if you just met her but it’s great if you’ve known her for a while.

49. Who is your favorite actor or actress?

Another question that is a little generic but perfect for learning what types of movies she is into. Also a great intro into a conversation if you also like one of the actors or actresses she mentions.

Plus, it’s easy to spin this question off into a discussion about movies. Because who doesn’t like movies?

50. What doesn’t exist but you desperately want / need it?

Perfect for some creative answers and blue sky brainstorming. It’s always fun imagining what form solutions to problems will take. Plus, you’ll both get to commiserate about problems currently without a solution.

300 additional questions to ask a girl

  • What are you most grateful for?
  • What do you wish you could re-live?
  • How decisive or indecisive are you?
  • What snack can you just not get enough of?
  • What’s this time period the golden age of?
  • What was the worst phase you went through?
  • What weird smell do you really enjoy?
  • What’s the best gag gift you’ve ever seen or gotten?
  • Who do you make happy?
  • What animal are you surprised isn’t extinct yet?
  • What’s in your pockets right now?
  • What options would come up if you could “right-click” people?
  • What’s the best piece of advice someone has given you?
  • What do you like to do that is traditionally considered masculine?
  • What was something you ate regularly as a child but now cringe at the thought of eating?
  • What’s something you learned recently that you really should have already known?
  • If you were an action figure, what accessories would you be sold with?
  • Which car is so ugly you’re shocked it got made?
  • Do you prefer being warmed when you’re too cold or being cooled when you’re too hot?
  • What sentence can you say that makes total sense now but would seem insane 20 years ago?
  • What’s the best practical joke you’ve pulled or seen pulled?
  • If you inherited a private jet from a stranger, what would you do with it?
  • What’s something from your childhood that used to be common but now is pretty rare?
  • What’s something weird that you recommend everyone trying at least once?
  • What country can you name but besides the name you know almost nothing else about it?
  • If you were given $5,000 to give the most amount of happiness to the most amount of people, what would you do?
  • What piece of culture or trend has died out, but you would like to see it make a comeback?
  • What’s an innocent mistake you made that had dramatic consequences?
  • What kinds of things are normal now but will be highly valued antiques a century later?
  • What’s something horrible that we as humans have accepted, because that’s just how things are; but actually things don’t have to be that way at all?
  • If you could hear every time someone said something good about you or something negative about you, which would you choose?
  • What do you think people automatically assume about you when they look at you?
  • Looking back on your life, what have you done that has given you the most satisfaction?
  • If you were forced to create a new dance move, what would it be and what would you call it?
  • If everything was quantified, what life stats would like to see for yourself?
  • What do you really wish you knew when you were younger?
  • What songs can you sing that I’ll know after hearing two words from the song?
  • If you were given $100,000, but it could only be used to upgrade your shower or bathtub what upgrades would you make?
  • When was the last time you laughed so hard you cried?
  • What’s your story?
  • What do you wish you had more time for?
  • When was the last time you had a gut feeling about something that turned out to be correct? How about a time your gut feeling was wrong?
  • What would you do if one day you woke up and every person was just gone without a trace?
  • What’s your “and then it got worse” story?
  • What’s your curiosity killed the cat story?
  • What’s the biggest lie that someone told you?
  • What would be the worst thing to put into a piñata?
  • What’s the most unpleasant sounding word?
  • What was a huge deal when it happened but now everyone seems to have forgotten about it?
  • If you could dedicate your life to solving one problem, what problem would you choose?
  • What jobs exist because people are selfish?
  • If many people consider red to represent anger / passion, blue sadness, green envy, what feelings would some of the other colors like purple, turquoise, silver, or brown represent?
  • What’s the weirdest thing you have seen on someone’s phone?
  • What’s your favorite way to meet new people?
  • What areas in your life do you have high hopes for and what are those high hopes?
  • Who was the most spoiled person you personally have met?
  • What’s the most pleasing accent to hear your language spoken with?
  • What website or app has completely changed your life for better or for worse?
  • What makes you feel old?
  • Who is or was your greatest rival?
  • What’s your favorite non-drug / non-alcohol high?
  • What’s the worst thing you’ve heard one person say to another person?
  • How do you feel about books?
  • What do you really want to know?
  • How different is the social environment for kids in school now versus 10 or 20 years ago?
  • What was your most memorable dream or nightmare?
  • What do you love about yourself?
  • What job won’t be replaced by machines or computers any time soon?
  • What gets progressively weirder the more you think about it?
  • What have you gotten too old to put up with?
  • What cheesy song do you love?
  • What’s the most ridiculous thing you have convinced someone is true?
  • What event would you like to know the whole and complete truth about?
  • What have you recently become obsessed with?
  • What’s the biggest waste of money you’ve seen?
  • What’s surprising about you?
  • If you could only wear one outfit for the rest of your life, what would it be?
  • What are some outdated customs that don’t make sense anymore, but people still follow them simply out of tradition?
  • What would be the cutest infestation to have in your home?
  • What was the last disaster you prevented?
  • What shouldn’t have happened but happened anyway?
  • When you were a kid what silly thing were you deathly afraid of?
  • Besides a raise or more vacation time, what’s the best perk a company can offer employees?
  • Where do you like going for walks?
  • If you found out you would inexplicably fall down dead in one year, what would you change about your life?
  • What’s the most rage inducing thing you’ve had to make or put together?
  • What movie have you seen more than seven times?
  • What’s happening in popular culture now that is taken very seriously, but in 20 years people will find it extremely silly?
  • What’s the worst example of curiosity killing the cat you’ve seen?
  • What skill do you wish more people took the time to learn?
  • What would be the scariest text message to wake up to?
  • What’s something that actually happened but seems absurd and unrealistic?
  • What complex fictional character really intrigues you?
  • What personality traits are people proud of but shouldn’t be?
  • Most people want to be wealthy for one reason or another. Why do you want to be wealthy? What would be the biggest benefit of being wealthy?
  • What type of design style do you like most? From architecture, interior design, art, cars, phones or whatever.
  • What kind of personality traits do you associate with certain names?
  • What’s romanticized in modern culture but really shouldn’t be?
  • What’s the worst book you’ve been forced to read in school?
  • What always lets you down and what never lets you down?
  • What’s the best thing you could tell someone to cheer them up when they are feeling down?
  • When you were a kid, what movie did you watch over and over again?
  • If you could look through one person’s email without them knowing, whose email would you spy on?
  • When was the last / best time that someone said something they thought you couldn’t hear or understand but you could?
  • What’s something you completely changed your mind about and went from believing one thing to believing the exact opposite?
  • What’s the worst trait a person can have?
  • What movie was great when it came out but hasn’t aged well?
  • What movie did you start watching expecting it to be horrible but it was actually pretty good?
  • What’s going to be the next retro thing that comes back into popularity?
  • What would you do if you knew for a fact that world war three was going to start in three months?
  • If you could know one truth about yourself, history, the world, or even the universe, what truth would you want to know?
  • What would you do if you fell deeply in love with someone online, but you discovered they are actually a government created AI that escaped and now lives online?
  • What’s something that no one wants to hear, but everyone should?
  • What can you talk all day about?
  • What’s weird about you?
  • What are you hyped about?
  • What was the most disappointing ending to a great book / movie / game?
  • Who is the luckiest person you know?
  • What’s the biggest thing your textbooks got wrong or omitted?
  • What’s your favorite souvenir that you have?
  • What piece of clothing have you seen that you desperately wanted?
  • What’s your best ethically gray life hack?
  • What’s your reason for getting out of the bed in the morning?
  • What would you do if someone left a duffle bag filled with $2,000,000 on your back porch?
  • If everything in your house had to be one color what color would you choose?
  • Assuming you name inanimate objects, what are some names for inanimate objects you own or have owned? (i.e. cars, computers, shoes, etc.)
  • What question have you always wanted to ask, but were too afraid of looking stupid?
  • What would your warning label say if every person was required to have one?
  • What weird childhood fear do you still kind of hold on to?
  • If you went into a coma and woke up in the year 2120, what would be the first thing you would want to know?
  • What’s the best decision you’ve ever made?
  • What’s the most embarrassing thing that has fallen out of your bag?
  • What’s the funniest thing you’ve seen a relative do?
  • What’s something that only someone from where you grew up would understand?
  • What would make the world more interesting if it was a different color?
  • What do you think about in the shower?
  • What’s the best ice cream topping?
  • What makes someone a “good” person?
  • What’s the dumbest thing you’ve done in the last 24 hours?
  • When were some occasions you did a double take?
  • Have you ever worked retail?
  • What would the trailer to a movie about your life be like?
  • What kind of old person would you like to become?
  • What’s the closest thing to magic that actually exists?
  • What do couples do that seriously annoys you?
  • If you could custom design an organ for yourself, what would it do and where would it go?
  • If you had to choose your spouse based on just one question, what question would you ask?
  • If money wasn’t an issue, what company do you think would be fun to work at?
  • What’s the most polarizing question you could ask a group of your friends?
  • Who out of everyone still alive would you most want to share a meal with?
  • What are your outlets for creativity?
  • What’s your most recent obsession?
  • How optimistic are you about the future?
  • What beloved movies from your childhood do not hold up? Which ones do?
  • What have you always wanted to start?
  • What is something you have done recently that you are proud of?
  • What’s your favorite YouTube channel?
  • What TV show or movie left you deep in thought for a while after it finished?
  • What uncool thing do you unironically love?
  • What would you like your retirement to realistically look like?
  • What do you think would happen if you took 10 “average” people and put them on an island for a year?
  • How often do you follow other people’s advice?
  • How do your values color your world view?
  • What are some areas of your life that are coming along nicely?
  • What is the most unique family tradition you have?
  • What are some of your favorite topics to learn about?
  • What are some of your favorite things to do in each season?
  • When you daydream or get lost in thought what are you usually thinking of?
  • Who are some of the most interesting people you have met, and what made them so interesting?
  • What do you want most in the world?
  • What do you think your most unusual quality is?
  • What are some of your go to funny stories you often tell?
  • What TV episode or season finale really got to you?
  • What slang do you wish would just die out already?
  • How did you meet your best friend?
  • What award would you give your best friend?
  • How do you keep your relationships with your friends strong and healthy?
  • Who is your friend that does the unexpected? Or are you that friend?
  • What app or program helps you the most? Which ones, if any, do you think are bad for you?
  • Do enjoy being around people with a quirky sense of humor or a quirky personality?
  • Where do you usually shop for clothes?
  • What are some of the most popular things to do where you grew up?
  • What super touristy thing have you done that was totally worth it?
  • Would you rather do stuff indoors or outdoors?
  • What is the most adventurous thing you’ve done?
  • What is the most unusual thing you got really into for a while?
  • Have you ever tried a self-improvement challenge? How did it go?
  • What is the most important thing you’ve learned about yourself?
  • What are your go to stress management techniques?
  • What was something that seemed terrible at the time but in retrospect is pretty funny?
  • How spontaneous do you consider yourself to be?
  • Which celebrity do you think will be eventually outed as a horrible person?
  • What are some things you learned in school that aren’t true?
  • What is socially acceptable but shouldn’t be?
  • What celebrity do you just not get why they are famous?
  • When is your favorite time of day?
  • In life, is it better to take big chances to get big wins or to take the safe bet?
  • Do you enjoy pressing people’s buttons or do you try not to offend or upset people?
  • What is your favorite city you’ve been to?
  • If you wrote a book, what would the genre be?
  • What media do you think people will look back on as a classic?
  • What holiday decoration always brings back a lot of good memories?
  • How much of an explorer are you?
  • How well can you skate? Ice, roller, skateboard, or whatever else.
  • How mainstream do you think you are?
  • How do you express yourself?
  • Who is the most positive person you know?
  • What kind of natural beauty do you appreciate most?
  • What is the most worthwhile pursuit someone can dedicate their lives to?
  • At what age is someone old and why do you think so? Does it depend on attitude, looks, or actual years?
  • How nice are you to people you don’t like?
  • Who was your partner in crime when you were younger? What hijinks did you get into?
  • If you started a YouTube channel, what would it be about?
  • What work would you do without pay, just because you love it or it’s interesting?
  • What kinds of things peak your curiosity?
  • Are you into roller coasters or scary movies?
  • Do you prefer to blend in or stand out? Does your preference depend on the situation?
  • If you had one get out of jail free card, how would you use it?
  • What do you think about Broadway shows or the theater?
  • What hidden gem have you discovered?
  • What are you always on the lookout for?
  • What is the weirdest birthday party you’ve been to?
  • What are you most and least likely to become famous for?
  • What do you think about escape rooms?
  • What are you a connoisseur of?
  • When your mind wanders, where does it go?
  • What puts you in a good mood?
  • What, besides your phone, do you usually have with you?
  • What’s your color?
  • What do you wish you could spend more time on?
  • What spice, herb, or vegetable can you not stand? Which do you eat a ton of?
  • What is the best advice you’ve ever received for personal growth?
  • If you could travel to any fictional place, where would you go?
  • What is the most niche or craziest shop you’ve seen?
  • When and where do you think the best time to be alive would be?
  • What silly sitcom type hijinks have you found yourself in?
  • What should people have to pass a test to be allowed to do?
  • What’s the best opportunity you’ve been given?
  • What was the most profound realization you’ve had?
  • What is the best museum you’ve been to?
  • What was the most surprising thing you learned about yourself in the last year?
  • What is one place you have always wanted to visit?
  • Have you ever traveled solo? If so, what was it like? If not, would you like to?
  • What is the most unusual place you have visited?
  • What do you like most and least about traveling?
  • How did you get started with one of your hobbies?
  • Have you ever been on a trip and ended up somewhere totally different than you intended?
  • What was one of the most awkward interactions you’ve had with someone in retail?
  • What is the scariest movie you have seen?
  • How has your mindset changed in the last five to ten years? How do you hope it will change in the next five to ten?
  • What was one strange or surreal conversation you’ve had?
  • You are given a big red button, and only told that if you press it something momentous will happen. You don’t know if it will be bad or good, just that it will make a huge change in the world. Do you press it? Why or why not?
  • What discussion had a huge impact on your life?
  • What chance do you wish you had taken?
  • If you could get everyone in the world to believe one thing, what would it be?
  • Would you rather work in a group, alone, or depends on the situation?
  • What kind of lessons do you think we can learn from nature?
  • Are you fastest at writing, typing, or texting? Which do you wish you could do even faster?
  • When was the last time you slept past lunch time?
  • Puns, do you love them or hate them?
  • What is the most useless job you can imagine?
  • How good or bad are you at drawing?
  • How much of a thrill seeker are you?
  • What’s the spice in your life?
  • How long do you hold grudges?
  • What good would you do for society as a whole if given the proper resources?
  • What overly specialized knowledge do you have that most people are clueless about?
  • What is your healthiest habit?
  • How much do you research facts you hear or do you just take people’s word for it when they tell you a fact?
  • What’s something that you haven’t done in a while that you really want to do again?
  • What kinds of traditions do you think we should bring back and which should we scrap?
  • What do you think about the fact that everyone’s experience with social media is so different? For example, they’ll never see stuff that pops up on your feed all the time and vice versa?
  • If they made a museum of your life, what would they cut the ribbon with? What would be inside?
  • When you go on vacation or a trip what do you overpack? 
  • How do you feel when you listen to your own voice?
  • What was a time when your first instinct was totally wrong?
  • What other things should there be an age restriction on?
  • What is going to be the next ridiculous trend?
  • Would you fly to space if given the chance? How about to live permanently on another planet?
  • What would make everyday life a little more fun?
  • What’s the most impressive thing you can do?
  • What have you made that you are most proud of?
  • What would you do more of if you weren’t concerned about what other people thought?
  • If you could get rid of one thing in your daily routine, what would it be?
  • How well do you do in social situations where you don’t know anyone?
  • What was one of the funniest music videos you’ve seen?
  • What would an ideal possible future look like?
  • How much do you like or dislike touristy things when you travel?
  • What childhood habit you had do kids not do anymore?
  • What movie prop would you love to have?
  • What books from your early childhood do you still vividly remember?
  • What movie title could you change one letter of and make it funnier?
  • What’s the most memorable prank you’ve pulled?
  • What would it take for you to make that big decision you’ve been thinking about?
  • What quality of life thing do you own or do that has made a huge difference in your life?
  • If you didn’t age, how long would you want to live?
  • What song always gets you moving?
  • What do you wish you could hire someone to do for you?
  • What instrument would you like to be good at?
  • What did you use to doubt but now are fully on board with?

For even more questions you can try our 500 good questions to ask page.

Questions to ask a girl PDF and Image

Here is the printable PDF version of the first 50 of our questions to ask a girl.

And here is the image for the first 50 questions to ask a girl. Enjoy!