70 Questions to Ask a Guy

The best questions to ask a guy give him something to talk about beyond "good" or "fine": a story, an opinion, a plan. Below are 70 of them: to get to know him, fun and random, questions for a guy you like, for a first date and for texting, and a set of deeper questions for when you are already talking for hours.

Duoo Games 4 min

70 Questions to Ask a Guy
In this article
  1. A few tips first
  2. Questions to get to know him
  3. Fun and random questions to ask a guy
  4. Questions to ask a guy you like
  5. Questions to ask a guy on a first date
  6. Questions to ask a guy over text
  7. Deeper questions to ask a guy
  8. Turn it into a game

A few tips first

  • Ask about things he likes. People talk more about what they care about.
  • Swap answers. Share your own answer to every question you ask.
  • Let quiet moments happen. He may need a second to think. Don’t fill it with the next question.

Questions to get to know him

  1. What do you do when you have a free weekend?
  2. What is something you are really into right now?
  3. What did you want to be when you were a kid?
  4. Where is the best place you have ever traveled?
  5. Who is your oldest friend, and how did you meet?
  6. What is a sport or game you have always loved?
  7. What is your favorite thing to cook?
  8. What is something you are working on getting better at?
  9. Which band or artist have you listened to the most this year?
  10. What is a movie you can quote way too much of?
  11. What does a perfect morning look like for you?
  12. What is your family like?

Fun and random questions to ask a guy

  1. What is the most useless skill you have?
  2. What would you do with a million dollars and one week?
  3. Which video game or movie world would you live in?
  4. What is the dumbest way you have ever hurt yourself?
  5. What is a food you refuse to eat?
  6. If you could be famous for one thing, what would it be?
  7. Which superhero do you think is overrated?
  8. What is the worst purchase you have ever made?
  9. What is the best meal you have ever had?
  10. If you had to compete in the Olympics, which sport would you pick?
  11. What is a conspiracy theory you secretly kind of like?
  12. What is the funniest thing your friends tease you about?

Questions to ask a guy you like

  1. What was the best part of your week?
  2. What is your idea of a great night out?
  3. What is something you have always wanted to try?
  4. What is a compliment you got that stuck with you?
  5. What are you most excited about right now?
  6. What is a small thing that makes you happy?
  7. If we went on a trip tomorrow, where should we go?
  8. What is a song you have had on repeat?
  9. What is something people usually don’t guess about you?
  10. What is the best date you have ever been on?
  11. What is one thing you want to do before the end of the year?

Questions to ask a guy on a first date

  1. What do you like most about your job?
  2. What is a trip you would love to take?
  3. How did you end up living where you live?
  4. What do your friends rely on you for?
  5. What is the last thing you learned that excited you?
  6. What is your favorite way to spend a Friday night?
  7. What is a hobby you would like to get into?
  8. What is something that always makes you laugh?
  9. Which restaurant around here is underrated?
  10. What is a family tradition you like?

Questions to ask a guy over text

  1. What are you up to tonight?
  2. What was the best part of your day?
  3. Recommend me a song.
  4. What did you have for lunch?
  5. Best and worst part of your day, go.
  6. What is the best thing you’ve watched lately?
  7. What are your plans this weekend?
  8. If you could be anywhere right now, where would you be?
  9. What’s the most random thing you saw today?
  10. What is the view from where you are right now?

Deeper questions to ask a guy

  1. What is something you are proud of that you don’t talk about much?
  2. Who taught you the most about how to live?
  3. What is a fear you have that might surprise people?
  4. What does success mean to you?
  5. What is a mistake that taught you something?
  6. What kind of day leaves you completely recharged?
  7. What is something you would like to change about yourself?
  8. How do you deal with a bad day?
  9. What is a goal you have not told many people?
  10. What is the best advice your dad, mom or someone older gave you?
  11. What makes a friendship last for you?
  12. What would you do if you knew nobody would judge you?
  13. Which place feels the most like home to you?
  14. Who do you go to when things are hard?
  15. What do you want your life to look like in ten years?

Turn it into a game

If a question list feels too formal, make it a game: try Two Truths and a Lie, this or that questions or the 21 questions game.

Duoo is an iPhone and iPad app with question games for two or more players, including Would You Rather, Never Have I Ever and Who’s Most Likely To. It works offline on one phone. It is free to download, and a subscription with a free trial unlocks every game and category.

More lists: questions to ask your boyfriend, questions to ask a girl, questions to ask to get to know someone and questions to ask friends.

Save these lists for later

Screenshot them for game night or save them to Pinterest.

7 Questions to Get to Know Him – Questions to Ask a Guy Save
7 Fun & Random Questions to Ask a Guy Save
7 Questions to Ask a Guy You Like Save
7 Questions to Ask a Guy on a First Date Save
7 Questions to Ask a Guy Over Text Save
7 Deeper Questions to Ask a Guy Save

Questions

What should I ask a guy to get to know him? +

Ask about what he spends his time on and why: "What do you do when you have a free weekend?", "What is something you are really into right now?" or "What did you want to be when you were a kid?" Follow up on whatever he gets excited about.

What are good questions to ask a guy you like? +

Light, personal questions work best: "What was the best part of your week?", "What is something you have always wanted to try?" or "What is your idea of a great night out?" They show interest without putting him on the spot.

How do I keep a conversation going with a guy? +

Ask open questions, share your own answer, and pick up on details he mentions. If he says he went hiking, ask where and what the best part was. Conversations die from switching topics, not from a lack of questions.

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