Skip to Content

21 Questions To Ask A Guy: In Person or Over Text

Try 21 questions to ask a guy if you want to get to know someone better or alternatively if you are already in a committed relationship and want to dive further into the deep and meaningfuls together. This is such a fun game as you really can know your date partner on a deeper, more intimate level. These questions are equally quite fun in a group of friends.

If you think gee I would really like to know X but don’t know the right way to go about asking – put your question as one of 21 questions, make it a fun game and he will be none the wiser – trust me!

How to play 21 questions with a guy?

What I love most about this game is how simple and easy it is. Simply, make a list of the 21 questions you would like to know about your SO and they will do the same about you.

It might be questions to get to know them better on an intimate level or just really PG rated questions to see if the two of you are a good match! You might like to ask questions about his family, his previous relationships or just random fun questions about life – the choice is entirely yours.

Plus after you ask these questions you might get a really good sign if he’s interested (or not).

Thinking of questions can be pretty hard. So we have done the hard work for you (there really is no excuses for date night!) and made a list of 21 fun questions to ask a guy (by category!)


21 questions to ask a guy

When scrolling through this list and copying the 21 questions you like the best, the biggest tip I can give you is select the questions in accordance with the stage of your relationship. You don’t want to weird the other person out if it is just your second date and you want a full list and details of past relationships – Eeekk.

Questions for your Crush

Here are some great questions that you might want to ask to get to know your crush better:

  1. Who is your celebrity crush?
  2. What’s the best gift you’ve ever received and who was it from?
  3. What is your favorite thing about your career?
  4. Have you been into any serious relationship before?
  5. When in life have you been most nervous?
  6. What is your idea of a perfect date?
  7. Where is your favorite place in the world?
  8. What’s your zodiac sign?
  9. What is your favorite word?
  10. Tell me your three biggest pet peeves?
  11. What was your first impression of me when we met?
  12. If you were to start a family somewhere in the world, where would it be?
  13. When did you have your first kiss?
  14. What breaks your heart?
  15. What motivates you to work hard? 
  16. What are you passionate about?
  17. What is your best hobby?
  18. Who is your hero?
  19. Where have you traveled to before?
  20. What’s the most spontaneous thing you’ve ever done?
  21. What really makes you angry?

Flirty Questions to ask a guy

Here are some flirty questions to ask a guy during the game of 21 questions. If you want more inspiration, you can check out our dedicated post on flirty questions to ask a guy – there are 153 questions on that list!

  1. What would you say are the aspects that draw you to me?
  2. Name 3 of my body parts that you like the most?
  3. What color do you think would look best on me?
  4. Do you believe in love at first sight?
  5. Do you see me falling for you?
  6. Who was your teacher crush?
  7. Describe your ideal relationship?
  8. What do you think is the best pick up line?
  9. If I was a flower, what kind of flower would I be?
  10. What is something that you think sets me apart from other people?
  11. What famous actress do you think I’m most like?
  12. Do you like my outfit?
  13. What is your biggest turn off?
  14. Do you have a secret fantasy?
  15. Do you believe in having a soul mate?
  16. What is your favourite romantic movie?
  17. Do you believe in fate or destiny?
  18. What do you think is my favorite food?
  19. If we were to go on another date, where would you take me?
  20. What is refreshing about me?
  21. Do you often have dreams?

If you prefer a “Question Game” that does the hard work for you, here some of our favorites you could pick up:

Random Things you Might Wanna Know

We all love to know a random thing or two about the person we are dating. Here are some random things you might wanna know that you might like to add into your list of 21 questions.

  1. If You Had Three Wishes, What Would You Wish For?
  2. What’s The Most Beautiful Place You’ve Ever Seen?
  3. Do you believe in ghosts?
  4. Would you rather be covered in fur or covered in scales?
  5. Would you rather live in a tree house or in a cave?
  6. Have you ever worn makeup?
  7. Would you describe yourself as a good cook?
  8. What fictional character do you have a crush on?
  9. Do you prefer boxers or briefs?
  10. Would you rather be a rich person with no friends or a poor person with many friends?
  11. What’s The Strangest Thing In Your Refrigerator?
  12. If you could trade places with one person for a day, who would it be?
  13. Would you rather be royalty 1,000 years ago or an average person today?
  14. What Would You Rather Have: Love Or Money?
  15. Would you rather fly a kite or hike a mountain?
  16. What Was Your Best Memory Of High School?
  17. Tell us about your best performed prank?
  18. Do you think babies are cute?
  19. Would you rather be rich or famous?
  20. If you go to a restaurant and have terrible service, is it ever OK not to tip?
  21. What’s Your Favorite TV Show? 

Deep Questions to ask a guy

Want to get to know the person on a much, much deeper level. Here are the best deep questions to ask a guy to get to know him better. We would recommend saying this questions for a little further on in the relationship say date 5 or 6?

  1. Would you rather die before or after your partner?
  2. Would you rather find love or be successful career wise?
  3. If you see a homeless person asking for money, do you give them any?
  4. What is one behavior you never tolerate?
  5. What would the perfect you be like?
  6. What was the most awkward conversation you ever had with someone?
  7. Would you rather have an obsessed girlfriend or a hot, cheating one?
  8. Would you prefer a huge mansion in a poor area or a small cosy apartment in a rich area?
  9. What non-politician do you wish would run for office?
  10. What stops people from understanding themselves?
  11. What do you consider a wasted life?
  12. What was your favorite age growing up?
  13. What is a controversial opinion do you have?
  14. Do you think we will ever have a definitive answer for what is the meaning of life?
  15. Have you ever cheated on your S.O.?
  16. Is poverty an inevitable byproduct of human society?
  17. What song speaks to your soul?
  18. What event would you rather die than live through?
  19. After a bad day, would you rather hug your Mom or Dad?
  20. Would you rather sacrifice having kids if it meant meeting your true love?
  21. What do you consider your greatest success?

21 questions to ask a boy

If you are under say 16 and are on a teen date, you might need some PG questions. Here are the best questions to ask a boy you like:

  1. What was your favourite movie ever?
  2. What was the last book you read?
  3. Do you believe in aliens?
  4. What is your star sign?
  5. What is the best gift you’ve ever given someone?
  6. Would you rather spend the day inside or outside?
  7. Do you shower at night or in the morning?
  8. What’s the most cringeworthy outfit you’ve ever worn?
  9. What was the last show you binge-watched?
  10. What’s the best trip you’ve ever been on?
  11. Do you believe in Karma?
  12. What do you wish you were really good at?
  13. What’s your favorite type of music and why?
  14. If you were a dog, what kind of dog would you be?
  15. Would you rather watch a comedy movie or a horror movie?
  16. If you were an incredibly talented rapper, what would you want to rap about?
  17. What is the weirdest thing about your family?
  18. What’s the last concert you went to?
  19. If you had to rename yourself, what name would you choose?
  20. What are your hobbies?
  21. What is your favorite animated movie and why?

More Conversation Starters?

If you liked these questions you might also like to check out:



  • MC Miller

    MC Miller is a travel blogger and writer who has travelled America extensively and abroad to over 80 countries. He founded Couple Travel The World in 2017. Since then, he has spent over 6 years on the road as a full time travel couple. When he not traveling he likes to spend quality time with his partner Bett, planning our their next date or romantic getaway!

    View all posts