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95 Random Questions for Fun Conversations

We love when people have fun conversations so we brainstormed a list of random questions to ask a guy, a girl or your crush.   


Make date night more fun by creating a game out of these questions. Having great conversation starters handy when you are texting each other or when having a date night.


What are some random questions to ask?


We split our questions to ask into different categories, but they can mostly be mixed and matched. 


Read through them and make a list of your favorite ones to use for the next time you are together or chatting online.


random questions infographic

Funny random questions


  1. Do you yell at the TV? When people are being stupid or when watching sports or both?


  1. If you have any sisters or brothers, what was the meanest thing that you have ever done to them?


  1. What was the craziest thing that you did as a kid?


  1. Where would you like to live if you could live anywhere in the world?


  1. What is something that is really out of your comfort zone?


  1. Would you ever eat bugs?


  1. What kind of fantasy house would you like to live in? Tree house? Maybe a houseboat or modern mansion in the Hollywood hills? Etc.


  1. Would you ever go bungee jumping or rock climbing?


  1. Do you get upset when you lose at a sport or competition?


  1. What was the worst meal that you ever made or eaten?


random questions to ask a guy


  1. Did you ever belong to a secret club?


  1. Did you ever play a prank on someone that got you in trouble?


  1. What was the stupidest thing that you ever stole from someone?


  1. What horror movie really freaked you out as a kid? What about now?


  1. Would you rather time travel to the past or to the future?


  1. What alcoholic drink don’t you drink anymore because you got sick from it?


  1. What really stupid movie always makes you laugh?


  1. Tell the truth, you really like those cute pet videos right?


    19. Imagine you are able to influence people to do or act in a certain way, what would be your first instinct to have them do?


  1. Would you be embarrassed if someone looked at your Google search results?


random questions to ask over text infographic


Random questions to ask a girl 


  1. What is your favorite fine dining restaurant? What do you like to order?


  1. What items would you grab if you had to leave your home for an emergency?


  1. Have you ever collected anything? Do you still?


  1. What makes you unique?


  1. Do you like to receive flowers? What are your favorites?


  1. Was there any time that you were almost arrested?


  1. What social media apps do you love the most?


  1. How often are you on your phone?


  1. What sports do you enjoy the most to either watch or participate?


  1. Are you a competitive person?


   31. What were your favorite classes in school or college?


  1. Have you ever taken classes just for fun?


  1. What do you miss the most right now?


  1. What languages do you speak?


  1. Did you ever make a Tic Tok video?


  1. Have you ever been backstage at a concert? Who did you meet?


  1. What is your favorite sweet treat?


  1. Did you ever think that you were born in the wrong era?


  1. What was the most memorable vacation that you have taken? Who did you take it with?


  1. What makes you jealous?


  1. Who in your life do you always make time for?


  1. Have you ever spied on someone?


random questions to ask your crush


Random questions to ask a guy 


  1. Name a stupid guy thing that you and your friends do or have done?


  1. What have you done that you are most proud of?


  1. What is your most prized possession?


  1. Did you have fun when you were a kid?


  1. Did you ever bully anyone?


  1. How adventurous are you when you travel?


  1. Are you a Mr. Fix it?


  1. What was the last thing that you fixed and how did that go?


  1. Are you close with your mom? And dad?


  1. What movie can you watch over and over again?


  1. What apps on your phone are you on the most?


  1. What would you consider an epic road trip?


  1. Have you ever seen a tornado?


  1. What in your life has scared you the most?


  1. Would you rather have a bird or a snake as a pet?


  1. Have you ever taken a train trip? If not, would you like to travel that way?


  1. What trait do you hate about yourself?


   61.What do you think is your best quality?


21 random questions to ask over text infographic


Random questions about life 


  1. What are the most important things on your bucket list?


  1. What is the best part of your day?


  1. What is the hardest part of being isolated?


  1. What is the last random act of kindness that you did for someone?


  1. How are you in high pressure situations?


  1. Name a quote that has meaning for you.


  1. Who do you look up to as a mentor?


  1. What do you fear the most?


  1. What was one of the best experiences of your life?


  1. What was one of the hardest experiences or your life?


  1. What was the last thing that made you very anxious?


funny random questions to ask



Random questions to ask your boyfriend 


  1. What does it mean to you to be successful?


  1. Have you stalked an ex on social media?


  1. What useful skill do you have? Impress me…


  1. If you could start your life over, what would you do? And where would you go?


  1. What sport are you best at?


  1. Have you ever broken any bones?


  1. Do you like to gamble? If yes, what are your games of choice?


  1. What part of politics do you hate the most?


  1. If you could only eat 3 foods for a year, what would you choose?


Random questions to ask your crush


  1. What fruit do you hate?


  1. What do you tend to lose the most often?


  1. Do you believe in horoscopes?


  1. What lesson did you learn about being in isolation?


  1. How would you feel if you HAD to become a vegetarian?


  1. Are you a romantic?


  1. What do you like to enjoy the most when you are in nature?


   90. Have you ever gone camping? Tent or cabin?


  1. What is something that you find really interesting?


   92 Do you judge people?


  1. Are you a planner or are you more of a spontaneous person?


  1. What noise drives you nuts?


  1. Do you think that you generally have good or bad luck?


21 fun random questions infographic


Conclusion random questions to ask


We have lots of fun questions to ask for all different situations. So have fun and take your pick!

Now more than ever, people are taking their time to get to know someone.


 If you want to find or keep a relationship strong, you have to connect with them. Take the time to get to know them better, even if you have been together for a while. 


There is always something new to learn, so might as well have fun with our conversation starters and random questions to ask.


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36 Questions to Fall in Love

Questions to Ask your Crush that are Flirty, Funny & Cute

 21 Questions to Ask a Guy to Start a Conversation

110 Good Questions to Ask to Increase Intimacy

Funny Would you Rather Questions to ask Couples and Friends

What are the Best Date Night Questions?

13 First Date Conversation Starters + What Not to Say on a First Date

73 First Date Questions That lead to Insightful Conversations

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