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101 Interesting Questions to Ask for Engaging Conversations

Our list of interesting questions to ask a guy or girl will help you have fun and deep text or in person conversations. We tend to reminisce or tell a funny story   

that relates to the questions making it so much more interesting.


 We usually elaborate on the answer and THAT’S where we get to the good information! So have a fun and entertaining time, while connecting with each other.


Use these questions for date night or gatherings with your friends. Having meaningful and interesting conversations is the key to keeping all of our relationships strong.


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What are interesting questions to ask?


  1. What famous character would you love to play in a movie?


  1. What musician would you love to hang out with or have a jam session with?


  1. What instrument did you play as a kid?


     4. When did you first find out that Santa wasn’t real?


  1. What is your favorite Disney movie?


  1. What natural disaster movie really scared you?


  1. What word do you think is fun to say?


  1. What horror movie did you watch that you couldn’t sleep after?


  1. What do you think is the most relaxing sound?


  1. Have you ever invented anything?


  1. What was the best party that you have ever gone to?


  1. What holiday do you think has the best food?


  1. What smell transports you to a special memory?


  1. Did you ever have a recurring nightmare?


  1. What is something that you do that you would like to give up?


  1. What was the most meaningful gift that you have ever given and received?


  1. When was the last time that you laughed until you cried?


  1. What is your favorite game to play, board or video?


  1. Have you ever won something? What was it?


  1. Would you rather live in a luxurious tree house or a beach house?


  1. What is something that you wish you could be an expert in?


  1. Who do you think is the most beautiful actress, of any era?


  1. What old school toy did you love as a kid?


  1. Are you still friends with anyone from elementary school?


  1. What is your favorite way to shop?


  1. Do you enjoy or do you hate shopping?


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interesting questions to ask a guy


More interesting questions to ask


  1. Do you normally tell others what you think or do you keep your opinions to yourself?


  1. How would you describe your personality?


  1. If you were asked to be a travel guide for your home town, where would you suggest they visit?


  1. Where was the best pizza that you have ever had?


  1. What food are you a master at cooking?


  1. What songs are on your playlist right now?


  1. What was the last actual book that you read?


  1. What skill do you think is essential for everyone to learn?


  1. What is something that is lacking from society which is important to you?


  1. What is the most important to you in your career;  Security. creating something new or the amount of money? 


  1. What do you think drives you?


  1. If you were handed 50k with the stipulation that it had to be spent in the next month, what would you buy?


  1. What drives you nuts about social media?


  1. What is one conspiracy theory that you think is likely real?


  1. What is the most annoying thing that you do that people complain about?


  1. If you reached your most sought after goal, how do you think you would feel after?


  1. Has this year changed the way that you see the world?


  1. What historical figure do you think you would be friends with?


  1. What do you see when you think of your future?


  1. If you were to start over, what career would you choose?


  1. What event in your life had a huge impact?


  1. Do the people in your family have the same political beliefs as you do?


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Fun questions to ask


  1. What do you think when someone describes themselves as religious?


  1. What will the world look like in 20 years?


  1. What place have you visited that filled you with awe?


  1. What was something meaningful that you have done within the last month?


  1. What are the top 3 things that are most important to you at this moment?


  1. On the days when you want to do no work at all, how do you spend your day?


  1. Do you think it was easier to live in the 50’s, 80’s or now? Why?


  1. What do you think are the most important qualities of a boss? Why?


  1. Every family has someone that gets into the most arguments, who is it in your family?


  1. Who in your extended family do you like to avoid? Why?


  1. What was the last live performance that you went to?


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interesting questions to ask infographic


What are interesting questions to ask a guy?


Our interesting questions to ask a guy can also be used for a girl. Most of the questions can be mixed and matched.


 Each of our interesting questions to ask will allow you to get to know him better. So often you may want to know his perspective on something but don’t want to just “blurt it out.” 


Asking fun questions is an easy way to get the answers while disguising it as just a fun game.


  1. Which superhero is the one that could beat all the other superheroes?


  1. What is your alcoholic drink of choice?


  1. Which sports would you like to see an extreme version of?


  1. What sport would be amazing if you added alcohol?


  1. What habit do you have that would be the hardest to give up?


  1. What was your happiest holiday memory?


  1. Were you ever really lucky? What happened to you?


  1. When you think of someone really interesting, who comes to mind?


  1. What guy do you admire? Why?


  1. What is the first thing that you notice about a woman?


  1. What type of music do you listen to the most?


  1. When was the last time that you had a lot of fun?


  1. If someone asked you to take them to your favorite local restaurants, where would you take them?


Interesting questions to ask a guy


  1. What social media platform do you spend the most amount of time on?


  1. What sound makes you cringe?


  1. What smell do you like that is not universally liked? Gas, mulch, fire…


  1. What is something that a partner has done for you that was really special?


  1. What sports do you watch and which sports do you play?


  1. What is your favorite comedy movie of all time?


  1. Have you ever been on a diet or do you have a workout routine?


  1. What makes you feel uncomfortable?


  1. Do you like being in charge?


  1. Other than your parents, who are you the closest to in your family?


  1. What is one thing that you enjoy doing that no one knows?


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interesting questions to ask a girl


What are interesting questions to ask a girl?


Our goal when using our interesting questions to ask a girl is for you to get into some fun and deep conversations.


These questions will make your in person or text conversations more interesting and allow you to really get to know them better.


  1. What shows or series made 2020 survivable?


  1. What song/songs did you like to sing (imagining you were the singer) when you were young?


  1. Do you feel more or less happy with how things are going in the world?


  1. What is the first thing that you are going to do when the virus worry has passed?


  1. What is your favorite flower and flower scent?


  1. Do you believe in luck?


  1. If you could travel anywhere in the world for a month, where would you go?


  1. What do you plan your vacations around? Sports, food, exploring?


  1. What has someone done for you that was really memorable?


  1. Do brands make a difference anymore?


  1. If so, what companies or brands are you loyal to?


  1. What is something that you have never told anyone?


  1. Do you have a signature scent?


  1. What is the first thing that you notice about a guy?


  1. Do you like to be in charge? Under what circumstances?


  1. What do you want to accomplish in the next 5 years?


  1. Who do you admire as a leader?


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Conclusion interesting questions to ask


If this year has taught anyone anything it’s that there are many ways to keep important people in your life. It may look different to each of us, but at its core, communication is the key.


We connect with each other over conversations whether that is in person or virtual.


 People change, priorities change and having interesting questions to ask helps to keep our conversations flowing.


 Asking interesting questions helps us to really know each other at different points in our lives. Enjoy all of our fun, flirty and interesting questions to ask for some really insightful conversations.


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