What skill or talent do you wish you had or were better at? If you could have a superpower what would you want it to be? What are you passionate about? What is your favorite movie? Are you a cat person, a dog person, both or neither? What do you think is your greatest strength? If you had to be a vegetable, which vegetable would you least like to be? What was the last dream you had? If you could start a band, what kind would it be and would you name it? Were Ross and Rachel on a break? What was the first album you bought, and why did you buy it?
Where do you see yourself? What is your favorite mistake? Who do you look up to of the same sex? Who is your role model of the opposite sex? What are you doing?
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What is your favorite book? What is your guilty pleasure song? If you could choose a decade to grow up in, which would you choose? What was your first concert? What would your superpower be? And your superhero name? If you could live in any city, which would you choose? Could you spend a day without your phone? What about a week? The Rolling Stones or the Beatles?
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If you could be a type of beer, which would you be? What is the last book you read? Did you like it? If you could have any talent, which would you have? What was your AIM screenname? Why did you choose it? Would you like to go out again next week? If you were stranded on an island, what is one item you would take with you? Who is your favorite band or musician? Are you more of a morning person or night owl? Where would you go on your dream vacation?
Who is the closest person to you and why? What is your favorite childhood memory? What kind of hobbies do you enjoy? Do you have any fears? If so, what are they? What are your current goals in life? Do have a favorite color and why? What would you choose as your top meal? What is your favorite city you have been to? What is on your bucket list?
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If you had no fears, what would be the first thing you would do? Do you have siblings? Where did you grow up at? What do value in others? What is your favorite book you have read? What is one piece advice you would give to someone? What is your favorite cuisine to cook? Do you have any vices? Do you speak any other languages? If you had to describe yourself in three words, what would they be? What is your astrology sign? Do you have any awkward family traditions?
If you were an animal, what would you be and why? Do you have any pets? Are you an introvert, extrovert, or ambivert? How long have you lived here? Have you ever lived in another country? Are you more of an indoors or outdoors person? What is your favorite athletic activity? What are you known for amongst your friends? How do you unwind? What are you most grateful for? What is your favorite holiday? How do you celebrate it? What is the most interesting fact about you?
If you were to go on a road trip, where would you go?
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Who has impacted you the most in life? What is one thing you still want to learn? What is your favorite way to spend your time off? What brings you happiness in life? Do you have any pet peeves? If you were to be notable for something what would it be? What is the longest timespan you could live without your phone? What do you hate the most about modern dating? Has a book ever changed your life?
If aliens came to Earth, would you be scared of them or would you welcome them? Has a song ever made you cry? Why do you get up in the morning? If you could rewind time, what one moment would you want to relive? If you were famous, would you still want a relationship or would you sleep around? If you were free to murder one person without getting punished, would you? Do you think people are born good or born evil? Have you ever had a near-death experience? Would you rather be hideous or illiterate?
Have you ever had your heart broken? What was the first thing you masturbated to? Are you proud to tell people about your job or embarrassed about what you do? Do you resent your exes or do you wish them well?
If you got a girl pregnant, would you consider it a burden or a blessing? Do you like what you see when you look in the mirror? Have you ever written poetry? What about song lyrics? Who would you call if you only had moments left to live? Do you believe in magic? Do you believe in the afterlife?
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Do you usually go with your gut or with your brain? What celebrity do you think deserves more attention? Have you ever questioned your sexuality? Is there anyone in this world that you genuinly hate? Would the childhood version of you look up to the current version of you? How are you going to leave your mark on the world? Would you lie to keep your best friend out of prison? What type of imaginary scenarios do you create in your head? Do you consider yourself to be a good person? Do you think you have a purpose in life?
Are you following your dreams or have you given up on them? Which gender stereotype about men do you hate the most? If you could erase specific memories from your mind, would you? Do you love your pets as much as you love your human family members? Have you ever seen a ghost? If not, do you believe they exist? Which fictional character do you relate the most to? Would you choose to live forever if you had the opportunity?
Who was your hero when you were a little kid? How do you feel about me? Have you tried to Google me? How long have you prepared for this date?
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Do you easily get bored? Can we try not to touch our phones for half an hour? What do you like about me so far? Do you feel things deeply? Have you tried suppressing your emotions? Are you okay talking about feelings? Do you stare at your ceiling before you sleep? Which has a higher spot in your priority — relationship or career? Are you one of those people who consider dates as job interviews? Okay…so how many dates have you been on before this? How many hearts did you break in the past?
When is the right age for you to settle down? What would you do if I just start crying and screaming right now? Do you believe in astrology? If I tell you our zodiac signs are super compatible, will you agree on a second date? Have you ghosted someone before? Who has been the biggest influence on your life? What really makes you laugh? What should I know about you that I would never think to ask about? Have you traveled anywhere really cool lately? Is there anywhere else you would love to live, other than here? What do you feel most passionate about? What is your favorite thing to cook?
What is your absolute dream job? Do you consider yourself spontaneous, or a planner? How would your best friends describe you? What is a tradition your family had when you were a kid? When you were a kid, what did you hope to do when you grew up? What is one skill you wish you could be better at?
If you could donate to any charity, which charity would it be and why? In one word, how would you describe yourself? What do you find most attractive in a potential partner? If you were stuck on a deserted island, who would you choose to have with you? For what in your life do you feel most grateful? How many times a day do you try and use The Force?
Gun to your head, must choose one: Do you cheat when playing Monopoly most of the time or all of the time? Bulbasaur, Squirtle, or Charmander? You spot a terrifying-looking spider a foot away from you. How do you react? What do you think is the biggest problem in the world today? What do you think people should do about it?
More From Thought Catalog
If you could have lunch with anyone in the world, living or dead, who would you want to meet? Some of these 21 questions to ask a boy range from the simple emotional to the blatantly sexual. Not all will be appropriate, but if you are planning to be sexually intimate, they probably are. What do I need to know about your sex life? If you wanted to kiss me, where would you take me to make it perfect? Tell me what you think is the sexiest thing about yourself bonus question: These questions should elicit more questions from you and shouldn't merely be a quick checklist of questions.
Ask for elaboration when appropriate and if your guy is particularly brief when answering a question, you may want to ask some follow-up questions to get more details. For example, if "What do I need to know about your sex life? Are these 21 questions to ask a man not quite enough?
Keep on clicking to find even more questions to ask when dating! You don't want your date to feel like an interrogation or a job interview, so you'll have to take special precautions to make the question and answer process more bearable. You could each write down 21 questions for dating on scraps of paper--serious and fun so the mood doesn't get too heavy - and throw them into jars yours in one, his in another. Take turns fishing out dating questions to ask a guy and answering them. You could also play a game where, for every point scored, the person who earned the point gets to ask a question.
Just be sure to choose a game you're sure to win or tie, or you may find yourself doing all the talking. If your guy is competitive, he may be more willing to participate if you make it a game with rules and points. As mentioned above, write the questions on slips of paper and put them in a jar or bowl.