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100 Random Questions to Ask


When you are talking to someone- whether it be a friend, your biggest crush, or even your significant other, you may run out of things to say. Yes, it’s a terrible thing to have to go through, and I think we’ve all been there: you are talking to someone amazing and all of the sudden you sense the conversation is running cold. You don’t want the conversation to end, but your mind is drawing a blank- and even though you’ve reached into the depths of your mind, nothing is happening!

Okay, for moments like these, I am asking you to do ONE thing, and ONE thing only: Don’t panic! Want to know why? Because we have 100- yes, I said 100- random questions to ask someone. We have some very interesting and unique questions that will keep the conversation going for much, MUCH longer than you’d ever imagined. So the next time your convo is going cold, refer to this amazing list; we promise you won’t regret it, and neither will the person you’re talking to.

20 Questions to Ask a Guy

Just friends? Someone you may be interested in? Doesn’t matter! If you’re talking to a cool guy but you’ve run out of questions to ask, he will love being asked these fun questions. They are totally random but they will definitely help you get to know them better. Some deep, some just plain silly- they are all wonderful questions you will want to ask him ASAP!

  1. If you could marry one fictional character, who would it be?
  2. If you had all the money in the word, where would you want to live?
  3. What is your biggest weakness?
  4. What is your biggest fear?
  5. How would you describe yourself in just three words?
  6. What is your favorite extra-curricular activity?
  7. What is your biggest pet-peeve?
  8. What is the most embarrassing thing that has ever happened to you?
  9. Is there anything you are superstitious about?
  10. What is your dream job?
  11. Have you ever been arrested? If so, what were you arrested for?
  12. What is your favorite movie of all time?
  13. Do you keep up with the latest news? Why or why not?
  14. If you could have superpower, what superpower would you choose, and why?
  15. What is the biggest regret you have in your life?
  16. What is your favorite television show?
  17. If you could only eat one food for the rest of your life, what food would you pick?
  18. Has anyone ever walked in on you when you were naked?
  19. Would you rather stay up late or wake up early?
  20. What am I thinking about right now?

20 Questions to Ask a Girl

Girls LOVE to be asked questions, but you have to make sure you’re asking the RIGHT questions. These 20 questions are sure to be adored by ladies around the world, and they’re great for those moments when you simply don’t know what to say anymore! These 20 questions are sure to amp up your entire conversation and give you something to talk about for a very long time.

  1. What is one quirky habit that you have?
  2. What is something you’ve always wanted to try?
  3. If you could live anywhere in the world, where would you want to live?
  4. What is the happiest memory you have from your childhood?
  5. If you could put together your dream date, what would happen?
  6. If you could change something about your looks, what would you change and why?
  7. What career would you love to have?
  8. Are you close with your family? Why or why not?
  9. What is your biggest goal in life?
  10. Do you believe that everything in life truly happens for a reason?
  11. Do you think it is better to follow your heart or follow your head? What is the reason for your answer?
  12. Do you have a favorite stuffed animal from when you were a child that you still own?
  13. What kinds of things make you laugh the most?
  14. What is the worst pick-up line you have ever heard from a guy?
  15. What is the funniest thing that’s ever happened to you in your life?
  16. If you could be any animal, what animal would you pick and why?
  17. If you could go back in time and change one thing from your past, what would it be and why?
  18. Would you want to know the time and place of your death?
  19. What would you grab from your house if it was on fire?
  20. Who are your biggest role models and why?

20 Questions to Ask Your Crush

Crushing on someone is HARD- you want to get to know them better SO badly, but having those butterflies in your stomach every time they come around or talk to you can leave you feeling tongue-tied. Once again, have no fear! These 20 questions to ask your crush will ensure you’re learning more about them while ALSO being subtly flirty. They’ll take a slight hint that you’re interested, without making you look needy or creepy. The best part is you will be flirting without even knowing it, and will also learn a ton about your new found crush.

  1. Have you been working out lately?
  2. What are some of the things you are looking for in a guy/girl?
  3. What would your dream date be like? Describe it in detail.
  4. What makes you laugh the most?
  5. What do you think about me? Be honest!
  6. Which celebrity do you have a crush on?
  7. Do you think a guy or a girl should make the first move?
  8. How many relationships have you been in?
  9. Have you ever been in love?
  10. Are you looking for a boyfriend/girlfriend right now?
  11. What are your favorite pet names for your boyfriend/girlfriend to call you?
  12. How would you describe me in 3 words?
  13. What is the naughtiest thing you have ever done?
  14. If you could have 3 wishes granted, what would you wish for?
  15. What do you think about true love? Is it real?
  16. What do you think is needed in order to make a great relationship?
  17. What is one thing you really want to learn or do?
  18. Do you play sports? Watch sports?
  19. What is your favorite feature on a guy/girl?
  20. What are your deal-breakers?

20 Questions to Ask Your Boyfriend

I am sure you and your boyfriend have a ton of things to talk about day in and day out, but even the most solid relationships have a cold conversation every now and then, and there is absolutely nothing wrong with getting to know your significant other deeper and finding out more about their thoughts on you and the relationship overall. These 20 questions will help you find out everything you need to know about your partner, which is great for making your entire relationship better and stronger in the end.

  1. When did you first realize you liked me?
  2. If we ever got married one day in the future, where would you want to go on our honeymoon?
  3. If I ever had to move away for school/work, would you come with me?
  4. Do you think you and I are soul mates?
  5. What was your very first impression of me when we met?
  6. What was the first thing about me that you were attracted to?
  7. How would you describe our first kiss?
  8. Is there a song that makes you think of me? What is it?
  9. What is your favorite physical feature of mine?
  10. Where is your favorite place to be kissed?
  11. Do I make you happy?
  12. Do you want a future with me?
  13. Which outfit of mine do you like the best? Why?
  14. Do you ever talk about me with your guy friends? What do you say?
  15. Am I the kind of girl your parents would like you to be with?
  16. If I were to make you dinner, what would you want me to make?
  17. Do you let me win games?
  18. What is the craziest thing you would do for me?
  19. What does love mean to you?
  20. What is something you’re afraid to tell me?

20 Questions to Ask Your Girlfriend

Your girlfriend loves it when you ask her questions- hands down! But what kind of questions should you really be asking her? These questions will help you learn more about her and what’s going on in her mind. You will also learn her favorite things, her idea of perfect dates, what makes her smile, and what romantic things you SHOULD be doing for her- plus so much more! You can’t go wrong with that, can you? Of course not!

  1. What is your idea of the perfect date?
  2. What is the one thing you like about me the most? Why?
  3. What is one thing that really impresses you?
  4. What do you like me to wear the most? Why?
  5. If we could go anywhere in the world for a weekend, where would you want to go and why?
  6. Do you have any heroes? Why do you consider them a hero?
  7. What are some of your best memories from your childhood?
  8. Do you think your family will like me?
  9. What is your favorite thing to do in bed?
  10. What makes you feel loved the most?
  11. What is your favorite romantic gesture?
  12. What makes you the happiest in life?
  13. What is your favorite pet-name?
  14. What is your biggest worry at this moment?
  15. What is one thing you would love to change in your life right now?
  16. How do you think our relationship could be even better?
  17. What is something in your life you truly appreciate?
  18. Do you remember the first time you met me? What did you think of me?
  19. What made you fall for me?
  20. Do you ever want to get married?


After checking out these questions, there is really no reason why you should EVER run into another cold conversation situation. But we are dying to know, did you like these questions? What are some other questions you would ask your guy/girl friends? What about your crush or significant other? Share with us your favorite random questions below!


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