350 Questions to Ask a Guy (He’ll Actually Like Answering)

Quick Usage Guide

• Start with easy conversation games, then move to being playful or flirty, and go further if everyone is comfortable.

• Always ask questions that can be answered with more than one word, like "Why?" and "Tell me more."

• Look out for signs that they are uncomfortable and don't cross any boundaries.If the answers are short, move on to a lighter topic.

• Save your favourites to: - turn something into a shareable card - create visual prompts - start a multimedia Q&A journal

Full list — 350 Questions to Ask a Guy (Categorized & Numbered)

Icebreakers & First-Meet Questions

1. Are you from around here, or did you grow up somewhere else?

2. What brought you to this city, college or company?

3. What has been the best part of your week so far?

4. Do you have any favourite local coffee shops or places to get lunch?

5. Are you an early bird or a night owl?

6. What music have you been enjoying recently?

7. Do you have any pets?

8. What do you like to do at the weekend?

9. What's your favourite season and why?

10. What was the last show or podcast you loved?

11. Do you prefer books or movies?Which one do you like best?

12. Have you found any fun hobbies recently?

13. What's your favourite comfort food?

14. Do you like to cook? What's your signature dish?

15. Are you someone who travels a lot, or someone who is more comfortable at home?

16. Tell us about one city you'd love to visit and why.

17. Do you collect anything?

18. What was your favourite game as a child?

19. Would you like coffee, tea or something else?

20. What sport do you enjoy watching or playing?

21. What have you learned recently that you didn't expect?

22. Do you prefer mountains, beach, or city breaks?

23. What's the best meal you've ever had?

24. Where do you go to relax when you need a break?

25. What app do you use most on your phone?

26. What small thing makes your day better?

27. What kind of movies do you watch a lot?

28. Do you prefer live concerts or a quiet night at home?

29. Do you like podcasts? Can you recommend any?

30. What was your childhood nickname (if you had one)?

31. Do you prefer museums or outdoor adventures?

32. What did you do on a whim recently?

33. Do you like to plan or do you prefer to just go with the flow?

34. What are you looking forward to in the near future?

35. If you had to choose, which local place would you show a visitor first?

36. Have you found any hidden gems in this city?

37. Do you like board games or video games?

38. What's the best free thing to do around here?

39. What random skill do you wish you had?

40. What's your favourite way to relax after work?

Flirty & Spicy Questions

1. What's your love language?

2. What's your best pick-up line?

3. Do you usually make the first move?

4. What kind of flirting do you like?

5. What would be your perfect date?

6. Do you like it when things are a bit slow or do you like to fall in love quickly?

7. What's your flirtiest quality?

8. What small thing makes you happy?

9. When was the last time you felt butterflies?

10. Do you feel bad about people seeing you and your partner together?

11. What makes you feel good right away?

12. Would you prefer a big romantic gesture or small, regular actions?

13. What's the boldest thing someone's ever said to you?

14. What would our first date look like if you planned it?

15. Who was your first crush?

16. Do you have a "type"?

17. What's your best relationship tip?

18. How do you show someone you like them without saying it?

19. Do you enjoy it when someone teases you?

20. What's a pet name you like that nobody else knows about?

21. When do you decide you like someone?

22. Would you rather whisper sweet nothings or send a cheeky text?

23. What's your favourite memory of feeling desired?

24. Do you think sparks are obvious or subtle?

25. What clothes make you feel most confident?

26. Have you ever been attracted to someone you didn't expect to be attracted to?

27. What's your favourite kind of kiss?(Answer in as simple or funny a way as you like.)

28. What would happen if we got stuck in an elevator together?

29. What would make you blush if you read that out loud?

30. Do you prefer holding hands or long hugs?

31. What signs show that someone is attracted to you, without saying a word?

32. What's the worst pick-up line you've heard?

33. Would you rather plan a surprise or be surprised?

34. Would you be the one to start, or wait for someone else to make the first move?

35. Do you like being chased or doing the chasing?

36. Where is your favourite place to enjoy a romantic moment?

37. What does romance smell like?

38. What makes you feel weak?

39. Do you like mysteries?Why or why not?

40. If you could tell me something quietly, what would it be?

Texting-Friendly Questions

1. How was your day?

2. What's one small thing you can do today to feel better?

3. What are you craving right now?

4. What song are you listening to over and over again?

5. If you could only bring three things with you on a trip, which three things would you choose?

6. Which emoji best describes you today?

7. What made you laugh out loud recently?

8. What's your favourite recipe?

9. Cats or dogs?Why?

10. What is one strange fact you know?

11. What did you enjoy most about your weekend?

12. What songs would you put on a playlist for me?

13. Do you prefer to call or text?

14. What's the most useless app on your phone?

15. What's one photo on your phone that always makes you smile?

16. What are you proud of doing recently?

17. Are you someone who always replies straight away, or someone who always says they'll reply later?

18. What show should I start watching?

19. Do you want a coffee or a cocktail tonight?(Just an example)

20. What do you want to try this month?

21. If you could teleport anywhere right now, where would you go?

22. What's your favourite comfort movie?

23. Which emoji best describes our conversation right now?

24. What would you tell your younger self every morning?

25. What makes your day better?

26. What was the strangest thing that happened in your dreams?

27. What are you currently enjoying?

28. If you sent me a photo of your view now, what would it show?

29. What do you want to learn this year?

30. What would your ideal Saturday morning look like?

Funny / Lighthearted Questions

1. Is it cereal soup?Why or why not?

2. Is a hot dog a sandwich?Now you can defend your answer.

3. What's the worst song you love in secret?

4. If you could be an animal for a day, which one would you choose?

5. What's the worst fashion mistake you've ever made and which you regret?

6. If your life had a theme song, what would it be?

7. What's the silliest thing you've Googled recently?

8. What's the funniest nickname you've ever been given?

9. Would you rather teleport or fly (but slowly)?

10. What would your superhero name be?

11. If you could erase one colour from existence, which one would it be?

12. What conspiracy theory do you think is true?

13. Which made-up world would you actually live in?

14. What's the worst thing to put on a buy-one-get-one-free sale?

15. If you had to wear one costume every day for a year, which would you choose?

16. What's your most ridiculous life hack?

17. Which food would make the ice cream flavour you like the least?

18. If you had to tell the story of your life, who would you choose to be the main character?

19. What's the funniest thing you've seen someone do in public?

20. If you were a pizza topping, which would you be?

21. What talent do you have that doesn't really help you?

22. What's the funniest prank you've ever pulled?

23. Which emoji do you use too often?

24. What smells do you like that make you feel good?

25. If you could make a rule that everyone had to follow for a day, what would it be?

26. What was your worst cooking disaster?

27. What would your plan be if there was a zombie apocalypse?

28. What's the funniest autocorrect error you've seen?

29. If you could be on any game show, which one would you choose?

30. What's the strangest gift you've ever received?

31. If your pet could talk, what would they say?

32. Which two famous people would you send to a desert island with?

33. What is the strangest food combination you like to try?

34. If you had to hum your favourite song right now, what would it be?

35. What's the worst pick-up line you've heard?

36. If you could delete one fashion trend, which would it be?

37. What's the most ridiculous thing you've ever pretended to know?

38. If your phone could talk, what would it say?

39. If you could choose any kitchen tool to use as a weapon in a funny movie, which one would it be?

40. What's the best Wi-Fi name you've seen?

Personal & Getting-to-Know (Moderate Depth)

1. What is your favourite memory from when you were a child?

2. Who had the greatest influence on you growing up?

3. What are the most important values you try to live by?

4. What are you proud of achieving?

5. Have you ever changed your mind a lot about something important?

6. How do you usually deal with stress?

7. What makes you feel truly understood?

8. Is there something you have experienced in your life but you don't talk about with many people?

9. What are the most important things for you in a strong friendship?

10. Did you have a teacher who had a big effect on your life?How?

11. What does success look like for you?

12. What do you think you'll be doing in five years?

13. Did you get the job you wanted as a child?If not, what changed?

14. What does "family" mean to you?

15. Have you ever failed at something that taught you more than success did?

16. Which time in your past do you miss the most?

17. How do you balance having enough money and enjoying yourself?

18. Do you have any spiritual or mental-health practices?

19. What are you working on to grow as a person?

20. How important is your physical health?

21. What would you give up to be more comfortable?

22. What's the bravest thing you've ever done?

23. What lesson from your parents did you take on board?

24. Is there a book that changed how you think?

25. Which childhood fear have you outgrown?

26. Do you make decisions based on logic or on your feelings?

27. What do you think people like most about you?

28. What would you spend your time on if you had no money?

29. If you wrote a memoir, which chapter would you put first?

30. What makes a friendship meaningful?

31. Has a misunderstanding ever made you grow as a person?

32. How did you deal with the worst thing that happened to you?

33. What does an apology that is sincere look like?

34. Which of your traits do you feel most grateful for?

35. What would you tell your younger self today?

36. How can you tell the difference between forgiveness and forgetting?

37. Who do you most often ask for advice?

38. What values would you want to pass on to future generations?

39. What makes you stop trusting someone straight away?

40. Do you ask for help or do things by yourself?

41. What kind of person do you want people to remember you as?

42. What makes a long relationship work?

43. Is there a principle you live by that few people know?

44. What makes your life worthwhile?

45. Would you move to another country for a better job?

46. Which do you prefer: being needed or being cherished?

47. What personal problem do you want to solve?

48. What small thing makes you really happy?

49. Where did you first make a close friend?

50. What three skills do you want to improve?

Random & Hypothetical

1. If you could have one superpower, what would it be?

2. If you could choose, which historical era would you like to live in?

3. If you had to eat one food for a whole month, which food would it be?

4. Would you upload your memories to the cloud if you could?

5. If you could change one thing that had happened in the past, what would it be?

6. Would you be happy living humbly for five years to achieve a dream later?

7. Who from history would you invite to dinner?

8. If you could only feel one emotion, which would it be?

9. Would you change careers completely tomorrow if you could?

10. What hobby would you like to turn into a full-time job?

11. Would you give up social media for a year for something big?

12. Which made-up world would you live in?

13. Can you travel through time to the past or the future? And why would you want to?

14. Would you like to know the date of your death?Why or why not?

15. If you had a million dollars today, what would you do first?

16. If you could, which language do you think you could learn the most quickly?

17. Would you give up stability to make art?

18. If you could make one unusual thing legal all over the world, what would it be?

19. If you could spend one day of your life again and again, which day would you choose?

20. Would you be able to retire early if you had enough money?

21. If you could instantly master a skill, what would it be?

22. What would you do if you didn't have a phone for a week?

23. Would you give up on your dreams for someone you love?Why or why not?

24. Where would you like to wake up tomorrow, anywhere in the world?

25. How much privacy would you give up to be famous?

26. Would you live in space for a while?Why or why not?

27. If you could change one law, which would it be?

28. If you could choose a new name for yourself, what name would you pick?

29. Would you do something nice that no one would ever know about?

30. If you could remove one global problem overnight, which would it be?

31. Would you be friends with an advanced AI?Why or why not?

32. If you wrote a book, what would it be called?

33. If you could save any endangered animal, which would you choose?

34. Would you live under the ocean if you could?

35. If you could live in three countries, which would you choose?

36. Would you press a button that taught you everything instantly?

37. Would you swap one memory for one million dollars?Why?

38. If you could fix one human weakness, which would it be?

39. If you could invite three people (alive or dead) to dinner, who would you invite?

40. Would you accept a challenge that could change the world?

Deep & Meaningful

1. Deep and meaningful, from 241 to 290.

2. Which failure taught you the most?

3. What is something you never told your parents but wish you could?

4. What does happiness mean to you?

5. What do you fear most in a relationship?

6. How do people actually start to trust each other?

7. When you feel lonely, what do you do?

8. Is there a memory you wish you could forget?

9. Do you feel like you are living your true self right now?

10. How do you deal with past hurts?

11. What action feels like a betrayal to you?

12. When did you last change a deep belief and why?

13. What did you learn from your low point?

14. How do you personally experience forgiveness?

15. When do you think someone should give up on a long-term goal?

16. What does taking responsibility look like to you?

17. What quality do you think is most rare in people?

18. Is there something you keep putting off that matters?

19. What would you tell your future self in five years?

20. How do you think parents' roles are changing in today's world?

21. Do you believe in soulmates?Why or why not?

22. What are you most afraid to talk about?

23. What happens when we die?

24. Would you give up your comfort for a strong belief?For example?

25. How do you tell the difference between what you should do and what you want to do?

26. When you're in an argument, do you back off or stick up for yourself?

27. How does culture influence life choices?

28. If a relationship is imperfect, how can it be fixed?

29. What are the three most important qualities you look for in a friend?

30. What's the hardest part of changing as a person?

31. How do you tell the difference between being alone and feeling lonely?

32. If you could keep one memory forever, which would it be?

33. What are your main hopes and fears for the future?

34. What do you believe with absolute certainty?

35. Where does your self-worth come from?

36. Which of these problems do you worry about the most?

37. Have you ever given something up because you were afraid of losing it?

38. When is it right to let someone go?

39. What would you like your loved ones to say about you when they think of you in the future?

40. What would make your life meaningful and successful?

41. If you could say anything without getting into trouble, who would you tell and what would you say?

42. What small behaviour makes someone trustworthy?

43. Is being kind to yourself important to you?Why?

44. How do you decide if a relationship is worth your time?

45. How do you balance wanting to help and looking after yourself?

46. Do you make major life decisions based on reason or feeling?

47. Do you think people can really change?Why or why not?

48. What would you tell the next generation?

49. What's the best pace for you?

50. If you could talk to a past version of yourself, what would you say?

VIII. Romantic & Relationship Questions

1. What's the most romantic thing you can think of?

2. Do you think "love is easy, staying together is hard" — why or why not?

3. How do you like to receive love?(Please give some examples.)

4. What is the most important thing for you in a partner?

5. What's the best way to sort out an argument?

6. What's the most romantic thing you've ever done?

7. What are the three things that couples should plan together?

8. What do you think family life will be like in the future?

9. What's your favourite way to celebrate anniversaries?

10. Which memory of us do you love the most?

11. Do you think that in a relationship, both people need to give and take?

12. What strange things are charming, and what things are not OK?

13. Do you prefer to cool off after fights or talk immediately?

14. How does managing our time affect our relationship?

15. Are there any secrets that a partner should keep to themselves, or share with others?

16. What does marriage mean to you?

17. Do you want kids? How would you raise them?

18. How should couples handle money together?

19. What helps a relationship stay fresh?

20. When things get tough, where do you get the most support from?

21. Do you have rules about how you use social media when you're in a relationship?

22. What shows respect in everyday interactions?

23. Would you change your habits for someone you love?Which?

24. Are romantic secrets ever OK?Why?

25. How would you plan a special five-year celebration for us?

26. If we became distant, how would we stay close?

27. What tradition would you like us to start?

28. Do you think romantic rituals are important?

29. Have you ever done something for someone you love that you didn't expect to do?For example?

30. Which relationship moment was the most important for you?

Serious Compatibility Questions

1. What are the most important things for you in life right now (your job, your family, your partner, yourself)?

2. What things are really important to you when you're looking for a long-term partner?

3. Which do you prefer, city or countryside, for raising a family?

4. What's the best way for couples to share their money?

5. How important is religion/spirituality to you?

6. What are your thoughts on parenting and discipline?

7. How do you want your partner to interact with your family?

8. Would you move for your partner?When might this happen?

9. Do you want pets? How many and what kind?

10. How should household chores be divided?

11. Can you be friends with an ex?Why or why not?

12. What limits do you think should be placed on friendships between men and women?

13. Would you like to go out for dinner and a show?

14. What responsibilities would you share with a partner?

15. How much are you willing to compromise in the long term for the relationship?

16. What does marriage mean to you?

17. How much independence do you want in a partnership?

18. What are some long-term goals that partners should set together?

19. What are your expectations for a partner's health and fitness habits?

20. Which approach to resolving conflict works best for you?

For Boyfriends & Long-Term Partners

1. How have you changed since we got together?

2. What are you most excited about for our future?

3. Is there something you want to tell me but you haven't yet?

4. Which moment do you keep replaying in your head?

5. What are the three things you like about me?

6. How can we improve our communication now?

7. What do you think we should do if we don't agree?

8. What do you think I need to know about your needs?

9. What little things make us feel like a team?

10. In five years, what would you like us to remember about you?

Expert Notes & Authority Mentions

• The Gottman Institute is a place where people do research on how to have good conversations and how to make relationshipslast.

• American Psychological Association (APA): studies on conversation quality and social bonding.

• Harvard Health/Harvard Business Review: research on how talking about things can improve mental wellbeing.

Turn these into multi-media on TellSomething

• Interactive question cards (with text and images or videos)

• Question and answer journals for couples or friends (save the answers, and add photos and videos).

• Carousels that are ready to use on social media and PDFs that you can print out