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21 Questions to Ask a Guy! (ASK IF YOU DARE!!)

My friend Jeremy is one of those guys who just loves to ask questions to people! I appreciate it about him. Most people live in a world where there’s blank and awkward silence. Truly—most people hate that! So when it comes to starting conversations—Jeremy know’s what is up! That’s why when he asked me, “Ryan, I need some advice—what are 21 questions to ask a guy to get to know him better?” I thought, well, I love that game! And I can help!

21 questions is a classic game that almost anyone can play. The point of the game is to enable two players to engage in conversation starters. These questions are exchanged back and forth between Player A and Player B. Each question is asked twice (once to each player). When you veer away from the questions—don’t worry—the entire point of the game is to engage in fun conversation topics and typically… take you away from asking more questions.

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21 questions to ask a guy: What’s one thing you value about yourself!?

21 Questions to Ask a Guy (If You DARE!)

Questions to ask during game play! Ask a few for a great conversation starter! Have fun!

21 Questions About Life

Fun questions to ask about life!

  1. Who is your best friend in life?
  2. What’s your biggest regret about your life so far?
  3. What did you think of me when you first met me? What was your first impression?
  4. Would you ever tell the waiter if you were having terrible service at a restaurant?
  5. Did you ever build a tree house when you were a kid?
  6. What’s the weirdest thing that you’ve ever done in life so far?
  7. What is your fun way to spend Sundays? (Hint: Idea list is here!)
  8. Don’t lie—what’s your favorite song that is embarrassing to tell?
  9. Which type of foods are your favorite foods (sweet, savory, salty, or other?)
  10. The last concert you went to was which one?
  11. If you had a time machine, where would you travel to and why?
  12. Who was your favorite cartoon character when you were growing up?
  13. The last TV show you binge-watched, GO!
  14. Worst thing about malls, go!
  15. What was the last cringeworthy outfit that you ever wore?
  16. Biggest fear in life… GO!
  17. Do you believe gender roles are real?
  18. What was the last spontaneous thing that you ever did with friends?
  19. What’s the worst lie you ever told your parents?
  20. Have you ever been in trouble with the police?
  21. How many pet peeves do you have? (Hint: PET PEEVES LIST HERE!)

Related: Random questions to ask a guy

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Ones to Ask About Family

It’s all about family! Questions about a particular family member or your family as a whole!

  1. When’s the last time someone made the joke ‘pretty good story’ to you when you told a not-so-funny story?
  2. What’s your earliest memory as a child/baby?
  3. What are some of your favorite movies to watch with your family members?
  4. Don’t lie—best gift you’ve ever gotten from a sibling!
  5. Favorite character that your mom/dad acts out when they’re trying to be funny!
  6. What’s an embarrassing thing that your family does that you don’t want people to know about?
  7. Weirdest dream you’ve ever had about your family… GO!
  8. Did you ever tell your mom/dad about your first kiss?
  9. Which fictional character do you think best describes your mom/dad?
  10. Do you know which celebrity crush your mom/dad has?
  11. What do you think your family would tell you about being in a healthy relationship?
  12. Favorite food to eat with your family, go!
  13. Favorite movie to watch on a Sunday with your family, GO!
  14. Did your mom/dad ever make fun of you for having your first serious relationship?
  15. What happens when your family walks up to a homeless person? Do they give them money or walk away?
  16. Does your mom/dad ever ask you deep questions about life or are they surface people?
  17. If your mom/dad had to tell you something about your younger-self, what do you think they would say?
  18. Who did you go to when you were heart broken as a teen: your mom or dad?
  19. Who is more fun—your siblings or your parents?
  20. Does your family like to have a low key holiday or do they travel?
  21. What’s one Christmas tradition that your family can’t go one year without doing?
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21 questions to ask a guy: Make sure he’s the one! Ask away!

Bucket List 21 Questions to Ask

Do these before you CROAK! This is a big deal!

  1. What is your ideal dream job?
  2. What activity/sport do you want to do before you pass away?
  3. Place you want to travel to before you go!
  4. One thing that you want to do before you pass away, GO!
  5. How much money do you wish to have before you pass away?
  6. How many kids do you want to have before you go?
  7. What would be the name of your first grandchild (if you had to pick)?
  8. Don’t lie—what are the values that you want your family to have when you’re older?
  9. Would you ever want to go sky diving before you pass away?
  10. What’s one bucket list item that you are embarrassed to tell people?
  11. Do you have a list of things that you want to do before you leave this Earth?
  12. Would you want to get closer to God before you decide to go?
  13. What’s one thing that you wish you didn’t do in life?
  14. How much money do you wish you could donate before you go?
  15. What’s going to be in your last will?
  16. If you were to record a video that’s played at your funeral, what would the video say?
  17. Would you want to be buried or be cremated?
  18. Do you want your name to get passed down to all of your kids?
  19. Would you ever go on a hot air balloon ride before you go?
  20. Is building a home for yourself on your list of things to do in life?
  21. Would you ever go back to school to get another degree before you go?

See also: Questions to ask a guy over text

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21 questions to ask a guy: Ask him about love and life!

Relationship 21 Questions to Use

If you have a love interest in this guy!

  1. Most cringeworthy outfit you’ve seen in public—GO!
  2. Favorite season of the year, GO!
  3. When was the last time you were in a long-term relationship?
  4. Would you ever get into a long-distance relationship?
  5. Do you believe in platonic soulmates?
  6. Do you think that we are secretly meant to be together based on our Zodiac signs?
  7. Is it possible that ‘love languages’ are a real thing?
  8. What’s one piece of advice on Instagram that you think is complete crap?
  9. What does your ABSOLUTE perfect date look like (with any person you’re with)?
  10. Do you believe in love at first sight?
  11. Is it possible the relationships are not for everyone?
  12. Are you a pet love? (I am a pet lover! But not everyone is!)
  13. Do you remember the name of your first crush?
  14. Who was the celebrity that inspired your ideal woman?
  15. Would you rather get to know someone on a deeper level or get to know someone on the surface?
  16. What’s one question that you ask to get to know the girl you like?
  17. What does your DREAM woman look like?
  18. If you had to describe the relationship you and your wife will have—what does it look like?
  19. Did past relationships ever leave you bruised? If so, why—what happened?
  20. What is the most interesting way that you can think of to spend the day together?
  21. What’s the WORST date you’ve ever been on—describe it to me!

Related: Flirty questions to ask a guy (complete list right here)

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Random and Funny Questions to Ask

When you want to get to know someone on an intimate level, but also laugh!

  1. Do you think feet are pretty?
  2. What’s one body part that you just can’t stand?
  3. Would you be willing to let someone clip their toe nails in front of you?
  4. Do you like the word “MOIST!?”
  5. Have you ever been fired from a job? If so, what happened?
  6. When was the last time that you farted in public?
  7. Who would you say that you look the most like?
  8. Has anyone ever told you that you looked like an embarrassing celebrity?
  9. What’s the WORST song that you really like?
  10. What is the WORST movie that you really like?
  11. Do you like plays and broadway?
  12. When was the last time that someone made fun of you?
  13. Have you ever tripped and fallen in public? If so, what happened?
  14. Which celebrity were you really into as a kid?
  15. How many times have you picked your nose in public?
  16. What’s the worst nickname you ever got as a child?
  17. Do you ever do something embarrassing in the car and think no body is watching? If so, what is it?
  18. Were you a good kid or a bad kid when growing up?
  19. Is there ever a time when two people can cheat on each other?
  20. Do you think that all relationships should be platonic?
  21. What’s one part of your body that is really TICKLISH!?

See also: Dirty questions to ask a guy

Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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