60 Random Questions to Ask a Guy (Best List)

💡 The Best List of Random Questions to Ask a Guy

Last update: 2021-05-12

Inside this article

  1. Random Questions
  2. Flirty Questions
  3. Funny Questions
  4. Keep the Conversation Going
  5. Deep Questions
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The best list of random questions to ask a guy.

Asking questions to a guy can be a great way to interact with them. Either you're a love interest. A friend. A family member. Or a colleague. Whatever your relationship with them, asking random questions to a guy can start conversations and pique curiosity. Often, leading to more in-depth conversations that take you two to new places.

Get to know someone better by asking conversation questions. Use this list of random questions to ask a guy in order to garner ideas about what you could ask. Have fun and start an interesting conversation!

What is a Conversation Starter?

A conversation starter is a question that's asked to someone else in order to start conversations. These questions are often unique. Or relatable. And help to encourage further discussion beyond the initial question. The main reason why they are called "conversation starters" is that each answer normally leads to further talking points and discussion. For example, a question about relationships can often lead to two people discussing values or morals in life.

Random Questions to Ask a Guy

The best list of random questions to ask a guy. Have fun, ask these interesting questions/conversation starters, and see where they go!

Random Questions to Ask a Guy You Like

These will surely get interesting answers!

  1. Would you rather go on a date with your best friend or turn your love interest into your best friend?
  2. If you had a million dollars, how would you spend it on me?
  3. What's your most interesting character as a guy?
  4. What do you think about the culture of men these days?
  5. If you could be any fictional character in a book or movie, who would it be and why?
  6. Presume you had to describe life in one word, what would you use and why?
  7. Assume you had to describe the meaning of love in one word, what word would it be?
  8. If you represented Earth while meeting aliens for the first time, what would you say?
  9. Why is the divorce rate in the United States so high?
  10. What do you think about new music releases right now?
  11. What's on your current Spotify Discover Weekly playlist?
  12. What was the last playlist you created?
  13. What's the last thing you watched on YouTube?
  14. Go into your search history, what's the last thing you looked up on Google?
  15. What's the craziest thing you've done with a crush?
  16. If you could live on another planet, which planet would you choose?

Flirty Random Questions to Ask a Guy

  1. Where is your favorite place to make out?
  2. Would you rather go out on the town during a date or have a long walk and talk?
  3. Do you appreciate talking on the phone or talking over text all day?
  4. What's something that guys should always do for their girl?
  5. If you could look like any celebrity, who would it be and why?
  6. Do you believe that men and women should have defined roles in the household?
  7. What's the worst date you've ever been on?
  8. What's the craziest thing you've done with a loved one?
  9. What weird activity would you want us to do on our second date?
  10. What's your least favorite thing to do with a girl in a relationship?
  11. What's your favorite game to play on the weekends?
  12. What would you like, for me to kiss you on your neck or on your hand?
  13. What's one thing that really turns you on about your crush?
  14. If you had all the money in the world, how would you spend it?
  15. What's one thing you've done with an ex-relationship that you aren't proud of?
  16. What is the funniest thing you've ever done on a date?

Funny Questions to Ask a Guy (Random)

  1. If you could be any food, what food would it be and why?
  2. Do you think that more apes will turn into humans in the future?
  3. Would you rather lead the relationship or had someone else lead the relationship?
  4. Who is one person in this world that you would marry, kill, and kiss?
  5. What's a funny story that you have about your life right now?
  6. What's something funny that you've done with your friends?
  7. Have you ever passed gas in front of a girlfriend?
  8. Have you ever had to use the bathroom for a long time on a first date?
  9. Did you ever ditch a date?
  10. Personal question: how long do you spend getting ready in the morning?
  11. Why did the idea of "beta males" become a thing in our society?
  12. Who is a person that you'd like to marry right now?
  13. What's one thing that you need to put in your bathroom drawer?
  14. What's the most embarrassing thing that your mom ever caught you doing?
  15. Who would win in a deathmatch, God or the Devil?
  16. What personal questions should someone avoid asking a new friend?

To Keep the Conversation Going

  1. What are your plans for this weekend?
  2. If you could choose to do anything this month, what would it be?
  3. Do you play any sports with your friends on the weekends?
  4. What movie or TV show are you going to watch tonight?
  5. If you were to go to a book store, what type of books would you be getting?
  6. When you're in a line at the grocery store, what magazine do you normally buy?
  7. When you're checking out at the grocery store, what snack do you normally get?
  8. What's your favorite unhealthy food snack?
  9. What is your favorite healthy food snack to have at night?
  10. Where do you see your friend's lives going in the next 5-years?
  11. If you had one friend go to prison, who do you think it would be?
  12. What would you rather be watching, hockey or football?
  13. Are you going to be watching any sports drafts this weekend?
  14. What's your favorite thing to bet on?
  15. If you had to play one game in Las Vegas right now, what game would it be?
  16. What's your biggest pet peeve about women in today's culture?

Random Deep Questions to Ask

  1. Is it weird that Adam and Eve were technically brother and sister?
  2. What do you think the implications of pornography are on society?
  3. Where do you think our culture is going?
  4. Do you think OnlyFans is good for our society and culture?
  5. How often do you pray to God?
  6. When you think about who God is, who do you believe you are talking to?
  7. Should we use the word "maybe" in our lives? Or only "yes" and "no?"
  8. If you could ask God anything about life, what would you want to know?
  9. Presume a fortune teller had to tell you the answers of the universe, what do you hope she/he would say?
  10. If you had to change something about your self-image, what would it be?
  11. Do you consider yourself a confident person or a secure person?
  12. What are your personal goals in life?
  13. What's something on your bucket list that you absolutely have to do before you die?
  14. Who was the last person you were in a relationship with and why didn't it work?
  15. Is categorized religion good for our culture and society?
  16. Who is someone in your life that you always consult when you have problems or issues?

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