400+ Questions to Ask A Girl You Care About

Do you need a list of great questions to ask a girl?

Getting to know each other is a key part of every relationship and the best easiest way to discover more about a lady is to ask her questions.

However, it is not always easy to come up with easy questions to ask a lady. If you don’t find interesting questions to ask her, she will ignore your message and focus on a more interesting conversation. It is logical, no one will never pick a boring or annoying conversation over a fun conversation. Therefore, knowing the right questions to ask a girl is a life and death issue for a relationship.

Aside, asking the right questions, you must also avoid going overboard. If you find yourself answering all the questions or asking all the questions, it isn’t a conversation; it is an interview. Surely, you don’t want your conversation to feel like an interrogation —it will surely drive her away! The best way to ensure you are both having a conversation rather than an interview is to ask open-ended questions. For example, How did you and your best friend meet? This question cannot be answered with a single word and it will lead to better conversations.

Also, be interested in her answers. Don’t just ask questions because you want to fill up the silence. If you ask a girl, how she met her best friend and she says she was really helpful during her late brother’s funeral. You have to acknowledge what she just told you, if not you will come across as insensitive.

Also, when you are just getting to know a lady, don’t get offended because she doesn’t feel comfortable answering a question. Eddie Murphy and Tracey Edmonds’ marriage lasted just fourteen days, so forgive her for taking a little time to establish that you’re trustworthy before she starts spilling her guts.

Certainly, there is a limit to the kind of questions you can ask someone you just met on the first date. Ensure you start with straightforward and harmless questions to make your date comfortable and then progress to deep and intimate questions.

Getting to know her questions
When you first meet me I’ll be quiet and shy, but if you show me you’re a good person and that I can trust you. I’ll slowly start to trust you, and once I have fully trusted you then, you’ll get to the know the real me.

Questions to Ask a Girl on the First Date

What are the best questions to ask a girl on the first date? On a first date, it is certain that both parties are nervous. Therefore, the best weapon in your arsenal is the use of icebreaking questions.

Start with simple questions that will make your date feel comfortable and relaxed. The beauty of ice breaker questions is that they help you set the tone for the conversation, and it will lead to several things you can talk about.

For example,

You: How’s the weather today?

Her: Well, I love winter, so …

You: What? I hate getting out of bed during winters, it is horrible!

She:  How do you not love winter? You know when I was your a little girl, I counted the days to winter…

You: Where did you grow up?

She: Portland

You: I grew up in Winterfell and we had a saying “Winter is coming”

She: Oh, Jon Snow! Nice to finally meet you in person

Larry King has interviewed thousands of people, and he recommends that you ask lots of questions, listen and ask some more. This is how you have interesting conversations.

These are good questions to ask a girl on your first date:

  1. All-time favorite movie?
  2. Are you a morning person or a night person?
  3. Are you good at accents?
  4. Are you single?
  5. Cook in or eat out?
  6. Describe your perfect day off.
  7. Do you believe in nicknames?
  8. Do you get used to being a celebrity?
  9. Do you have a hobby your friends don’t know about?
  10. Do you have Pets?
  11. Do you like pickles? (It is always fun to ask a random question.)
  12. Favorite board game?
  13. Favorite character on TV?
  14. Favorite sandwich?
  15. Have you ever met a celebrity?
  16. How did you pick your outfit?
  17. How do you spend your weekends?
  18. How do you take your coffee/tea?
  19. How long did it take you to put together this outfit?
  20. How was your sleep last night?
  21. How would someone get your special attention?
  22. If you could go anywhere in the world on vacation, where would you go?
  23. If you were (of the opposite sex) what would your name have been?
  24. If you weren’t here, what would you be up to right now?
  25. Most embarrassing moment?
  26. Most important quality in a friend?
  27. Proudest moment in high school?
  28. What characteristic do you most dislike in others?
  29. What characteristics do you admire (in self or others)?
  30. What do you like doing in your spare time?
  31. What foods do you dislike?
  32. What has been your best/worst date?
  33. What is the last book you read?
  34. What is your biggest/weirdest fear?
  35. What is your favorite color?
  36. What is your favorite dessert?
  37. What is your favorite drink?
  38. What is your favorite flower?
  39. What is your favorite food?
  40. What is your favorite kind of music?
  41. What is your favorite movie?
  42. What is your favorite restaurant?
  43. What is your favorite T.V. show?
  44. What is your favorite song?
  45. What movie star, musician or artist have you spent hours learning about?
  46. What other languages do you speak?
  47. What pet would you love to have?
  48. What sports do you enjoy doing?
  49. What time did you get up this morning?
  50. What was the highlight of the year for you?
  51. What was the last film you saw at the cinema?
  52. What were your best/worst subjects in school?
  53. What would be a good theme song for your life?
  54. What would be your one super power?
  55. What do you do for a living?
  56. What’s the most unusual job you’ve ever had?
  57. What’s your favorite season (summer, fall, winter, spring)?
  58. What’s your favorite travel destination? (been there or want to go)
  59. What’s your idea of the perfect day?
  60. What’s the weirdest thing a fan has ever done for you?
  61. What’s your biggest/most mysterious fear?
  62. What’s your one annoying habit?
  63. What’s your one biggest pet peeve?
  64. What’s your favorite Halloween costume?
  65. What’s your favorite holiday?
  66. Where would you like to visit?
  67. Where would you retire to?
  68. Who is your celebrity crush?
  69. Who is your inspiration?
  70. Would you date your best friend?

Random Questions To Ask a Girl

Random questions keep the conversation between you and her flowing. They can also lead to some significant discussions about love, dream, and life in general. Here are the top random questions to ask:

Who is the worst/best teacher/boss you’ve ever had?

There is always both interesting and funny stories attached to this question. It will help you establish what your girlfriend admired or hated in a boss or teacher. You will get to know what, based on her judgment, makes someone great.

Who is your favorite celebrity or who do you greatly look up to?

You will get to know what she thinks are great traits in a person as well as what inspires her among other things.

What’s one thing that you’ve never revealed to your dad or mom about?

Obviously, there are a lot of stuff that she has never revealed but dig deep to find out about one that she will NEVER tell them.

What’s the most boring or scariest movie you’ve watched?

Maybe she’s not into scary movies, but at least you will get to know where to take her on a date.

Do you have a hidden dream that you’ve never shared with anyone?

Sometimes people avoid sharing thoughts that they feel are precious to them for fear of failure or embarrassment. 

What do you fear most?

After all, you want to be her only safe harbor to come to for safety, healing, and soothing.

Is there anything adventurous you are proud of doing this year?

When inspiration strikes, people end up booking flights to their dream destinations. 

What can I do for you today?

You will have an opportunity to tailor your help to what she needs most at that particular moment or day.

What are up to this week or this month?

You will be able to tune your schedule to what she enjoys. Additionally, it will help you balance more dangerous or potentially negative questions or topics.

Can you describe your perfect day? Or if you are allowed to do anything you wished for a day, what would be?

This will help you plan for her activities, gifts, and dates among other things.

If you were given a chance to choose three things in life, what could they be?

You will get to know her fantasies and even her personal character

What’s the best thing that you’ve ever achieved or happened to you?

This will leave the conversation between you and her on a positive note. You will both get to reflect on happy and beautiful moments in your lives.

Who is your best celebrity couple?

There are cute couples out there that she admires. Draw inspiration from them

What’s your favorite restaurant or joint in town? And what is your favorite meal at home?

At some point, you will want to take her to a special date or dinner. It pays to know the restaurants and type of foods she loves.

What do you find yourself always procrastinating?

You will gauge how grounded she is—whether she is a more floaty type or goal oriented.

  • What is your favorite memory from childhood?
  • What do you plan to do immediately following graduation from college?
  • What types of decorations do you plan to have for your wedding party?
  • What was your high school experience like?
  • How did you and your best friend meet?
  • What sites do you expect to see on your vacation?
  • When was the last time you tried something new?
  • Are you happy with yourself?
  • Beyond the titles that others have given you, who are you?
  • Can you think of a time when impossible became possible?
  • Do you see to believe or believe to see?
  • For you, what makes today worth living?
  • How are you pursuing your dreams right now?
  • How do you define success?
  • How do you find the strength to do what you know in your heart is right?
  • How do you know when it’s time to continue holding on or time to let go?
  • How do you spend the majority of your free time?
  • How have you changed in the last five years?
  • How have you helped someone else recently?
  • How many of your friends would you trust with your life?
  • How short would your life have to be before you would start living differently today?
  • How will today matter in five years from now?
  • How would the world be different if you were never born?
  • How would you describe ‘freedom’ in your own words?
  • How would you describe yourself in one sentence?
  • If happiness was the national currency, what kind of work would make you rich?
  • If I could grant you one wish what would you wish for?
  • If someone could tell you the exact day and time you are going to die, would you want them to tell you?
  • If today was the last day of your life, who would you call and what would you tell them?
  • If today was the last day of your life, would you want to do what you are about to do today?
  • If you could ask one person, alive or dead, only one question, who would you ask and what would you ask?
  • If you could live one day of your life over again, what day would you choose?
  • If you could live the next 24 hours and then erase it and start over just once, what would you do?
  • If you could take a single photograph of your life, what would it look like?
  • If you left this life tomorrow, how would you be remembered?
  • If you were forced to eliminate every physical possession from your life with the exception of what could fit into a single backpack, what would you put in it?
  • If your life was a novel, what would be the title and how would your story end?
  • Is it better to have loved and lost or to have never loved at all?
  • Is it possible to know the truth without challenging it first?
  • Is the reward worth the risk?
  • Is there ever a time when giving up makes sense?
  • What are the primary components of a happy life?
  • What are three moral rules you will never break?
  • What are you looking forward to?
  • What are you sure of in your life?
  • What can money not buy?
  • What did you learn recently that changed the way you live?
  • What did you want to be when you grew up?
  • What do you have trouble seeing clearly in your mind?
  • What do you owe yourself?
  • What does it mean to allow another person to love you truly?
  • What has been the most terrifying moment of your life thus far?
  • What have you done in the last year that makes you proud?
  • What have you read online recently that inspired you?
  • What is the meaning of ‘peace’ to you?
  • What is the most important thing you could do right now in your personal life?
  • What is the number one thing you want to accomplish before you die?
  • What is your favorite song and why?
  • What is your fondest memory from the past three years?
  • What is your greatest challenge?
  • What is your greatest skill?
  • What is your most prized possession?
  • What is your number one goal for the next six months?
  • What makes a person beautiful?
  • What makes everyone smile?
  • What makes you proud?
  • What stands between you and happiness?
  • What word best describes the way you’ve spent the last month of your life?
  • What would you do if you made a mistake and somebody died?
  • What would you not give up for $1,000,000 in cash?
  • What would your ‘priceless’ MasterCard-style commercial be?
  • What’s the difference between settling for things and accepting the way things are?
  • What’s the next big step you need to take?
  • What’s your definition of heaven?
  • When do you feel most like yourself?
  • When does silence convey more meaning than words?
  • When have you worked hard and loved every minute of it?
  • When is love a weakness?
  • When you help someone do you ever think, “What’s in it for me?”
  • When you think of ‘home,’ what, specifically, do you think of?
  • Where do you find peace?
  • Who do you dream about?
  • Who do you think of first when you think of ‘success?’
  • Who do you trust and why?
  • Who is the strongest person you know?
  • Who or what do you think of when you think of love?
  • Why do religions that advocate unity divide the human race?
  • Why do you matter?
  • Would you ever give up your life to save someone else?
  • What is the nicest thing someone has ever done for you?
  • What do you see when you look into the future?
  • What makes you angry? Why?
  • What is the most valuable life lesson you learned from your parents?
  • What does love feel like?
  • What are your favorite simple pleasures?
  • If you could go back in time and tell a younger version of yourself one thing, what would you tell?
  • What do you do to impress others deliberately?
  • What will you never do?
  • In what way are you your own worst enemy?
  • When did you not speak up when you should have?

Deep Questions to Ask a Girl

An excellent way to nurture your connection is to talk about those inner worlds—because great communication extends beyond discussions of college life, and kids. Of course, these topics are also relevant, but delving into often overlooked and intimate conversations are much better.

How do you rate our sex life lately?

You will know her level of satisfaction with your recent sex life and if there is something she would like more of, less of, or different from what you have been having.

What are some of the things you consider unforgivable?

Her answer will depend on her life experiences. For instance, if she has been cheated on, she may find that inexcusable.

Do you follow your instincts or your heart when making decisions?

You will get to know if she’s a feeler or a thinker. If she chooses to answer both, try to encourage her to pick one that she follows most of the time.

Do you think everything happens for a reason?

Some people believe that everything in life is destiny, while others take life as a series of random events. You will get a real insight into where she stands. Plus, you will be able to arouse some interesting conversation between you and her.

How do I react when I am angry or when we disagree?

You will be able to identify any potential weakness that you may have when you are angry or when there is any form of conflict between you and her.

If I were to change one thing about myself, what would you like me to change?

This will give you a window into a few things she feels insecure about. It is an opportunity for you to be as compassionate and emphatic with her as possible.

Do you believe in marriage? Or what’s your take on committed relationships?

While for some ladies, marriage may appear as a traumatic thing, especially when their parents got divorced, for others it is the most important aspect because committed people tend to do everything to come up with solutions instead of creating problems. This is one of the most significant conversations that you should have at any rate, especially if you wish to go long-term with her. 

If we had one day to live together before the world ends, what do you suggest we’d do?

Well, it will be sad if truly the world was to end, but what’s cool with this question is that people lose all inhibition if it’s for one day only. 

When was the first/last time you had a crush on someone?

Some people had their first crash in kindergarten while others in high school. This question will evoke interesting stories and can bring you a good laugh, especially if things didn’t turn out well in their first crash.

  • When was the last time you tried something new?
  • Who do you sometimes compare yourself to?
  • What’s the most sensible thing you’ve ever heard someone say?
  • What gets you excited about life?
  • What life lesson did you learn the hard way?
  • What do you wish you spent more time doing five years ago?
  • Do you ask enough questions or do you settle for what you know?
  • Who do you love and what are you doing about it?
  • What’s an uncommon belief you hold?
  • What can you do today that you were not capable of a year ago?
  • Do you think crying is a sign of weakness or strength?
  • What would you do differently if you knew nobody would judge you?
  • Do you celebrate the things you do have?
  • What is the difference between living and existing?
  • If not now, then when?
  • Have you done anything lately worth remembering?
  • What does your joy look like today?
  • Is it possible to lie without saying a word?
  • If you had a friend who spoke to you in the same way that you sometimes speak to yourself, how long would you allow this person to be your friend?
  • Which activities make you lose track of time?
  • If you had to teach something, what would you teach?
  • What would you regret not fully doing, being or having in your life?
  • Are you holding onto something that you need to let go of?
  • When you are 80-years-old, what will matter to you the most?
  • When is it time to stop calculating risk and rewards and just do what you know is right?
  • How old would you be if you didn’t know how old you are?
  • Would you break the law to save a loved one?
  • What makes you smile?
  • When it’s all said and done, will you have said more than you’ve done?
  • If you had the opportunity to get a message across to a large group of people, what would your message be?
  • If the average human lifespan was 40 years, how would you live your life differently?
  • What do we all have in common besides our genes that make us human?
  • If you could choose one book as a mandatory read for all high school students, which book would you choose?
  • Would you rather have less work or more work of what you enjoy doing?
  • What is important enough to go to war over?
  • Which is worse, failing or never trying?
  • When was the last time you listened to the sound of your own breathing?
  • What’s something you know you do differently than most people?
  • What does ‘The American Dream’ mean to you?
  • Would you rather be a worried genius or a joyful simpleton?
  • If you could instill one piece of advice in a newborn baby’s mind, what advice would you give?
  • What is the most desirable trait another person can possess?
  • What are you most grateful for?
  • Is stealing to feed a starving child wrong?
  • What do you want most?
  • Are you more worried about doing things right, or doing the right things?
  • What has life taught you recently?
  • What is the one thing you would most like to change about the world?
  • Where do you find inspiration?
  • Can you describe your life in a six-word sentence?
  • What is the biggest loss you have suffered?
  • Do you like the city or town you live in?  Why or why not?
  • How many people do you love?
  • How would you describe the past year of your life in one sentence?
  • How would you spend your ideal day?
  • If you could relive yesterday what would you do differently?
  • If you had to move 3000 miles away, what one thing would you miss the most?
  • Right now, at this moment, what do you want most?
  • Through all of life’s twists and turns who has been there for you?
  • What are you looking forward to in the upcoming week?
  • What are you uncertain about?
  • What do you do over and over again that you hate doing?
  • What do you do to relieve stress?
  • What do you do with the majority of your money?
  • What do you think about when you lie awake in bed?
  • What do you understand today about your life that you did not understand a year ago?
  • What good comes from suffering?
  • What have you done that you are not proud of?
  • What is the biggest change you have made in your life in the last year?
  • What is the most spontaneous thing you’ve ever done?
  • What is the one primary quality you look for in a significant other?
  • What are your greatest strength and your greatest weakness?
  • What is your happiest memory?
  • What is your saddest memory?
  • What life lessons did you have to experience firsthand before you fully understood them?
  • What makes love last?
  • What makes you uncomfortable?
  • What makes you weird?
  • What motivates you to be your best?
  • What one ‘need’ and one ‘want’ will you strive to achieve in the next twelve months?
  • What or who has been distracting you?
  • What was your last major accomplishment?
  • What white lies do you often tell?
  • What will you never give up on?
  • What worries you about the future?
  • What would you like to change?
  • What’s something most people don’t know about you?
  • What’s the best decision you’ve ever made?
  • What’s the best part of being you?
  • What’s the most important lesson you’ve learned in the last year?
  • What’s your favorite true story that you enjoy sharing with others?
  • When should you reveal a secret that you promised you wouldn’t reveal?
  • When was the last time you lied?  What did you lie about?
  • When was the last time you lost your temper?  About what?
  • When you have a random hour of free time, what do you usually do?
  • When you look back over the past month, what single moment stands out?
  • When you look into the past, what do you miss the most?
  • Who is your mentor and what have you learned from them?
  • Whose life have you had the greatest impact on?
  • Would you rather your child be less attractive and extremely intelligent or extremely attractive and less intelligent?

Romantic Questions to Ask a Girl

Knowing what she loves when it comes to matters romance will enable you always to make it happen. Deep passionate talks are also, well, very romantic. As any relationship counselor would confirm, intimacy is part and parcel of what makes couples feel loved and happy.

What makes you feel cherished?

Well, girls are different. Not all women will feel loved or cherished because you bought them roses, nor will all women feel loved because you always take them out. As they say, love is a very complicated thing in many ways—in most cases, women need everything from appreciation, compliments, and gifts to the special time that you spend with them.

What’s your romantic dream trip or holiday?

Obviously, she will mention a destination, but don’t let her stop there—make her tell you what she would want to happen at the destination. Even if you can’t take her to Las Vegas, maybe you can surprise her with similar activities in nearby town.

How do you know somebody cares for you?

Not only will she knows that you care about her by simply asking the question, but you will also be in a position to know what to do when she’s sad or upset.

What’s your favorite or sexy clothing for men?

While you shouldn’t break the bank to change your wardrobe for her (don’t even try it because she will assume you have no spine), throwing in some outfits that drive her crazy is a very good idea. Plus, she might also get a chance to ask you what you would love her to wear, and it is certain you have several options in mind.

Which movies to you find romantic?

By knowing a few of her sexy or romantic movies, you will have clues on what she is looking for in life. You need to be careful, though, because it might be just a particular part of the movie that she’s interested or drawn to.

What music genre do you find romantic?

For some people, it’s Marvin Gaye, for others jazz will do. It is good to know as next time she might be coming over.

What do you think of being in a relationship? Is there anything you love?

Everyone in a relationship agrees that there are pros and cons of being single and being in a relationship. By highlighting some of the good stuff, there are high chances that she will realize just how happy and content she is with you!

Is there a day I have made you feel special?

If you have, you’ll immediately reflect what happened or what you did so that you can repeat it another day or do something similar. If you haven’t, it’s your chance to know the things she value!

Funny Questions to Ask a Girl

In a survey of 1000 American women conducted by Men’s Health, 77 percent of the women ranked a sense of humor as their preferred attribute in a man. Humor was ranked ahead of intelligence, passion, confidence, and generosity. Similarly, a Stanford study found that comedy could help people feel more comfortable in horrifying and uncomfortable situations.

One way to make her laugh is by knowing funny questions to ask her.

What’s the funniest pick-up line that you’ve heard in your lifetime?

If you are still young and haven’t had the chance of going to bars and clubs yet, this question might be irrelevant. However, if you are dating someone a bit mature, and she likes to go out, she has probably heard tons of interesting and side-splitting come-ons from men.

What’s your favorite comedy show?

This can bring a few laughing and fun moments

What’s the most embarrassing thing that you’ve ever done in your life?

It is normal. Everybody has ended up in some situations that they wish never happened. Sharing a few episodes can be hilarious

What’s the weirdest thing you’ve ever done?

It is a good idea to know. Who knows, you may be dating a maniac!

What are some of your funniest childhood memories?

Most people have been through a couple of funny situations in their childhood

What’s the worst thing that you’ve done to impress a man?

Everybody has been there. Enjoy the moment

Have you ever found yourself laughing at a time when it was totally inappropriate?

At times nervousness, fear, and feelings make people laugh at the wrong moments. Sharing a few of these moments is always fun.

What’s the weirdest dream you’ve ever had?

You might get a clue of her psyche

Interesting Questions to Ask a Girl

  • Have you ever been caught fooling around by a parent or a sibling?
  • Have you ever been embarrassed to pick up your pictures from the photo center, because you remembered what is on them?
  • Have you ever been fooling around in a car and accidentally honked the horn?
  • Have you ever been frisked by police or by airport personnel?
  • Have you ever been hit on by someone who was too old?
  • Have you ever been kicked or bitten by an animal?
  • Have you ever been on the radio or television?
  • Have you ever been out in the rain and enjoyed it?
  • Have you ever gone skydiving or scuba diving?
  • Have you ever snuck into a bar or a movie because you were underage?
  • Have you ever gone water skiing or snow skiing?
  • Have you ever broken a bone?
  • Have you ever broken something, like a window, and ran away?
  • Have you ever burped while you were kissing someone?
  • Have you ever cheated on a test or an exam?
  • Have you ever done something dumb while camping?
  • Have you ever dyed your hair, and it didn’t turn out well?
  • Have you ever eaten a whole cake or a pizza yourself?
  • Have you ever eaten frog legs or some other strange food?
  • Have you ever faked being sick so you could stay home or come home from school or work?
  • Have you ever fallen down the stairs?
  • Have you ever fooled around in a sleeping bag?
  • Have you ever found a wallet or money that someone dropped?
  • Have you ever gone “commando” (without wearing underwear)?
  • Have you ever gone on a “bad” blind date?
  • Have you ever gone skinny dipping?
  • Have you ever been arrested by mall security?
  • Have you ever gotten a tattoo?
  • Have you ever gotten in trouble at school or church?
  • Have you ever gotten lost at an amusement park or on vacation?
  • Have you ever become so sick, that you swore off a particular food or type of alcohol?
  • Have you ever had a blow-out tire while driving?
  • Have you ever had a friend who shared the same birthday as you?
  • Have you ever had a near-death experience?
  • Have you ever had food or a drink spilled on you at a restaurant or party?
  • Have you ever had sex in the back seat of a car, or the back of a truck?
  • Have you ever had sex with a person whose name you didn’t know
  • Have you ever had something embarrassing happen to you?
  • Have you ever had to get stitches?
  • Have you ever had your cell phone ring at an embarrassing moment?
  • Have you ever have you ever made up a story to get out of a traffic ticket?
  • Have you ever held a butterfly or another insect in your hand?
  • Have you ever held or petted a wild animal?
  • Have you ever helped someone who was in danger?
  • Have you ever hidden cigarettes or weed, so your parents wouldn’t know you were smoking?
  • Have you ever lied about not doing something you were supposed to do?
  • Have you ever lied about your age?
  • Have you ever lied about your birthday just to get a free dessert?
  • Have you ever lied to get something cheaper than it was?
  • Have you ever locked your keys in the car, or have been locked out of your house?
  • Have you ever lost part of your bathing suit?
  • Have you ever made a prank phone call?
  • Have you ever met a famous person or a celebrity?
  • Have you ever not been able to remember how you got somewhere?
  • Have you ever paid for a stranger’s meal or drink, without them knowing it was you?
  • Have you ever played a trick on someone, or had someone play a trick on you?
  • Have you ever played strip poker?
  • Have you ever pretended to speak a foreign language you don’t know?
  • Have you ever put someone’s hand in warm water to see if it would make them pee?
  • Have you ever regifted something that you received as a gift?
  • Have you ever ridden a ride that made you scream with fear?
  • Have you ever ridden on a cow, an elephant, or some strange animal?
  • Have you ever seen a human baby or a baby animal be born?
  • Have you ever seen an actual tornado (not on TV or in a movie)?
  • Have you ever seen the same movie more than twice in a theater?
  • Have you ever shared food with your dog or cat?
  • Have you ever showered with someone of the opposite sex?
  • Have you ever skinny-dipped?
  • Have you ever skipped a class or a whole day of school?
  • Have you ever smoked in the high school bathroom?
  • Have you ever spent the night sleeping by the toilet?
  • Have you ever spied on your neighbors?
  • Have you ever stayed awake for an entire night?
  • Have you ever stayed in your pajamas all day long?
  • Have you ever stuck out your tongue at the ATM camera?
  • Have you ever sunbathed partially or totally naked?
  • Have you ever sung in front of people by yourself?
  • Have you ever sung in the shower or on the toilet?
  • Have you ever sung karaoke, or did a lip-sync song?
  • Have you ever swam in ice cold water?
  • Have you ever taken a picture of your face on a Xerox machine?
  • Have you ever taken a pregnancy test?
  • Have you ever talked on the phone for more than two hours?
  • Have you ever talked your way out of getting in trouble?
  • Have you ever thrown up on an airplane or a boat?
  • Have you ever toilet-papered someone’s house?
  • Have you ever told someone their zipper was down or their shirt was popping open?
  • Have you ever tried to burp the alphabet?
  • Have you ever used a fake I.D. and then couldn’t remember your new name?
  • Have you ever went camping in a tent?
  • Have you ever went skydiving, bungee jumping, or parasailing?
  • Have you ever won a contest and received a prize?
  • Have you ever won a contest?
  • Have you ever worn special clothes to cover up a hickey?
  • Have you ever worn the same underwear two days in a row?
  • Would you rather be able to control animals with your mind or control electronics with your mind?
  • Would you rather be able to control fire or water?
  • Would you rather be able to teleport anywhere or be able to read minds?
  • Would you rather be beautiful/handsome or intelligent?
  • Would you rather be feared by all or loved by all?
  • Would you rather lose all of your memories from birth to now or lose your ability to make new long-term memories?

Personal Questions to Ask a Girl

  • Who is your hero?
  • If you could live anywhere, where would it be?
  • What is your biggest fear?
  • What is your favorite family vacation?
  • What would you change about yourself if you could?
  • What makes you angry?
  • What motivates you to work hard?
  • What is your favorite thing about your career?
  • What is your biggest complaint about your job?
  • What is your proudest accomplishment?
  • What is your child’s proudest accomplishment?
  • What is your favorite book to read?
  • What makes you laugh the most?
  • What was the last movie you went to? What did you think?
  • What did you want to be when you were small?
  • What does your child want to be when he/she grows up?
  • If you could choose to do anything for a day, what would it be?
  • What is your favorite game or sport to watch and play?
  • Who is your favorite author?
  • Have you ever had a nickname? What is it?
  • Do you like or dislike surprises? Why or why not?
  • How would your friends describe you?
  • What are your hobbies?
  • What is the best gift you have been given?
  • What is the worst gift you have received?
  • Aside from necessities, what one thing could you not go a day without?
  • Where do you see yourself in five years?
  • What’s your favorite zoo animal?
  • Have you ever had a secret admirer?
  • What’s your favorite holiday?
  • What’s the most daring thing you’ve ever done?
  • What was the last book you read?
  • Are you a clean or messy person?
  • What’s your favorite movie?
  • What’s the craziest thing you’ve done in the name of love?
  • What was your favorite subject in school?
  • What Motivates You To Succeed?
  • What’s Something Too Serious To Be Joked About?
  • In What Ways Are You The Same As Your Childhood Self?
  • Who was the last person that made you cry?
  • The most painful thing your parents have ever done to you?
  • One thing about your childhood you wish you could change?
  • What song would you say best sums you up?
  • Who was your first crush?
  • What was your first job?
  • What is one thing you will never do again?
  • Who knows you the best?
  • Are you an introvert or an extrovert?
  • Biggest Regret in life?
  • When last did you cry yourself to sleep?
  • Do you have a criminal record?
  • Do you believe in God?
  • Who did you vote for during the last elections?
  • Have you ever tested positive for STDs
  • Do you have a history of mental illness in your family?
  • What is the biggest health scare you’ve had?
  • Do you think the past matters in a relationship?
  • What gets you excited about life?
  • What life lesson did you learn the hard way?
  • What do you wish you spent more time doing five years ago?
  • Who do you love and what are you doing about it?
  • What’s belief that you hold with which many people disagree?
  • What can you do today that you were not capable of a year ago?
  • Do you think crying is a sign of weakness or strength?
  • What would you do differently if you knew nobody would judge you?
  • Are you holding onto something that you need to let go of?
  • Would you break the law to save a loved one?
  • What is important enough to go to war over?
  • If you could instill one piece of advice in a newborn baby’s mind, what advice would you give?
  • What is the most desirable trait another person can possess?
  • What are you most grateful for?
  • Where do you find inspiration?
  • What is the most defining moment of your life thus far?
  • Have you ever regretted something you did not say or do?
  • What is your most beloved childhood memory?
  • Is it more important to love or be loved?
  • If a doctor gave you five years to live, what would you try to accomplish?
  • What are your top five personal values?
  • What personal prisons have you built out of fears?
  • Are you happy with yourself?
  • Beyond the titles that others have given you, who are you?
  • Can you think of a time when impossible became possible?
  • Do you see to believe or believe to see?
  • For you, what makes today worth living?
  • How are you pursuing your dreams right now?
  • How do you define success?
  • How do you find the strength to do what you know in your heart is right?
  • How do you know when it’s time to continue holding on or time to let go?
  • How do you spend the majority of your free time?
  • How have you changed in the last five years?
  • How have you helped someone else recently?
  • How many of your friends would you trust with your life?
  • If you could ask one person, alive or dead, only one question, who would you ask and what would you ask?
  • If you could live one day of your life over again, what day would you choose?
  • If you could live the next 24 hours and then erase it and start over just once, what would you do?
  • If you could take a single photograph of your life, what would it look like?
  • Who do you trust and why?
  • Who is the strongest person you know?
  • What’s the biggest lie you once believed was true?
  • What’s the best part of growing older?

Bottom Line

Now you have numerous conversation starters and intimate questions you can ask any lady.

Remember! It is not an interview.

Questions cut both ways, so be prepared to answer her questions.

If you are better at this than the rest of us, save a life by dropping more questions in the comment box.

20 thoughts on “400+ Questions to Ask A Girl You Care About”

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