153 Interesting Questions to Ask a Guy to Spark Intimate Discussions

Do you want to start a conversation with a guy but are stuck for interesting questions to ask him? Regarding relationships, having meaningful conversations with your partner is key.

Whether you are in the early stages of getting to know him or have been together for years, finding interesting questions to ask a guy can help keep the conversation going.

To help get the ball rolling, here are 150+ interesting questions to ask a guy that can spark intimate discussions between the two of you.

These questions range from lighthearted topics about his hobbies and interests, to more serious questions about his values, beliefs, and goals in life.

Interesting Questions to Ask a Guy to Keep Conversation Going

If you’re looking for interesting topics to discuss or need inspiration for questions to ask your boyfriend, this list will provide you with many ideas. Here is a list of interesting questions to ask a guy:

1. When you need to unwind, where do you like to go?

2. Do you prefer to work out at the gym or at home?

3. Can you tell me about the last time you cried? And why did you cry?

4. Do you like to go camping or clubbing? Do you prefer my company for this?

5. What are your greatest fears? Is it a big deal for you?

6. Can you tell me about the nicest thing you’ve ever done for a woman?

7. What is the most thoughtful thing a woman has done for you?

8. What is your biggest dating obstacle? And why?

9. How can a woman gain your trust?

10. How many people have you seriously dated?

11. Have you ever dated someone your family hated?

12. Have you ever had a friend betray you?

13. What was one time you really stepped out of your comfort zone?

14. What makes you smile no matter what?

15. Give me three words that best describe who you are.

16. What is your ideal date type? And who do you prefer?

17. What is the most exciting vacation you’ve ever experienced? Do you want to experience it again?

18. Tell us about a country you’d like to visit.

19. What are some foods you would never eat? And why do you hate it?

20. What do you consider to be your most attractive physical feature?

21. What is it about me that you admire the most? And why?

22. What would you do if you could change jobs right now? Or are you satisfied with your current job?

23. What is your earliest memory of childhood? Can you tell the story of it?

24. What is one item that consistently irritates you? And why?

25. What do you believe to be your most great achievement to date?

26. What do you like best about where you live?

27. What is one feature about your current location that you truly hate?

28. Do you have a favorite Starbucks order?

29. What would you acquire if you could only get one present?

30. Would you rather get a present, gift cards, or cash?

31. Do you consider yourself to be an introvert or an extrovert?

32. If you could go back in time and change one thing about your life, what would it be?

Interesting Questions to Ask a Guy to Know Him Better

If you’re interested in getting to know someone better, asking interesting questions is a great way to start. Here will list some of the most interesting questions you can ask a guy to get to know him better.

Would you rather have someone act hostile to your face or pretend that they like you?

1. What is your star sign?

2. What is your favorite color?

3. What is your favorite decade of music?

4. If you could invite one artist to your wedding, who would it be?

5. Is there a fictional character you’d want to be more like?

6. What three words best describe you?

7. How does a rainy day make you feel?

8. Would you consider dumpster diving?

9. Would you say you’re closer to your parents or grandparents?

10. What is your favorite local restaurant/cafe?

11. Do you try to support local businesses over large corporations if you have a choice?

12. What really pumps you up and gets you going?

13. What’s one thing you do regularly and would never skip?

14. What are your thoughts on thrifting?

15. What is your biggest guilty pleasure?

16. What is your fashion taste?

17. Do you enjoy spending time alone?

18. Do you consider yourself a gamer?

19. What’s your favorite type of exercise?

20. Who is your favorite athlete?

21. Which college did you go to?

22. What were your majors in school?

23. Did you ever cheat on an exam?

24. What career path are you pursuing?

25. Were you excited to start working when you were finishing school?

26. Do you prefer games in which you cooperate or play against one another?

27. What was your first car?

Interesting Questions to Ask a Guy You Like

Here are some flirty and fun questions to ask a guy that will keep him engaged and interested in getting to know you better.

1. Is it important to you that people remember your birthday?

2. Do you ever feel like there’s nothing left to do in life?

3. Would you say you’re good at managing money?

4. Have you ever doubted your own sanity?

5. Did you ever talk back to your parents when you were a kid?

6. Have you ever participated in a ritual or a ceremony of any kind?

7. Have you ever physically hurt anyone?

8. What is your greatest personal value?

9. Have you ever written a published piece of work?

10. What is the most unhealthy habit you have?

11. Have you ever experienced some sort of abuse?

12. What is one thing you can never compromise on when it comes to relationships?

13. Have you ever had a sequence of things going wrong for you?

14. Do you think tertiary education is necessary?

15. What is your favorite music genre?

16. Would you like to have kids? If so, how many?

17. What is your greatest fear?

18. Where do you see yourself in five years?

19. How do you measure or define success?

20. Are you religious?

21. Is it easy for you to make friends?

22. Do you think any job/profession is beneath you? If so, what is it?

23. Have you ever bullied someone?

24. Are you proud of your family?

25. Do you ever feel like your family is trying to pull you down?

26. Have you ever argued with your significant other in public?

27. Has anyone in your family been directly affected by war?

Interesting Questions to Ask a Guy on a Date

If you’re looking for a fun and romantic way to get the conversation going on your next date, why not try asking some interesting questions? These are the question you can ask a guy on date:

1. Do you speak any other languages?

2. What’s your favorite video game?

3. What was the last movie you saw in theaters?

4. What network is your favorite show on?

5. What’s your favorite way to relax?

6. What’s one food that you could eat every day for the rest of your life?

7. Do you have a favorite cartoon?

8. Do you know how to juggle?

9. What’s a scene from a movie that you wish you could recreate in real life?

10. How many plants do you have in your apartment?

11. What’s the weirdest thing you’ve ever done to impress a potential love interest?

12. What’s the weirdest dream you’ve ever had?

13. What do you think has better material, Hulu or Netflix?

14. What’s one thing you’ve never been good at?

15. What’s your favorite fast food restaurant?

16. What’s your favorite food of all time?

17. What’s your mother’s name?

18. Where are you from?

19. What’s one website that you visit every day (email doesn’t count)?

20. Do you prefer the mountains to the ocean? Or the other way around?

21. What’s your favorite song?

22. Did you play sports as a kid?

23. What do you think your best quality is?

24. What about your worst?

25. Do you prefer going out or staying in on Saturday nights?

26. What subject did your favorite teacher from high school teach?

27. Do you prefer a good movie or a good book?

28. Do you have any useless skills?

29. What food grosses you out?

30. Do you like old films?

31. Would you ever vacation in the same place twice?

32. Can you teach me to make your favorite ethnic food?

33. Are you a mountain or a beach person?

34. What are the things you spend the most money on?

Interesting Questions to Ask a Guy Over Text

Texting is a great way to ask these questions without feeling awkward or uncomfortable. You can follow our interesting questions to ask a guy list to make a good time over the text.

1. What’s the worst text you’ve ever sent by accident?

2. Who is your celebrity crush?

3. Which animal would you like if you could be one?

4. If you could be a superhero, who would you be?

5. What are your hidden talents?

6. What word would you use to describe yourself if you had to choose only one?

7. What has been your most memorable life experience to date?

8. What is your favorite movie of all time?

9. How do you usually spend your weekends?

10. What is the most important thing you’ve learned in life?

11. What’s the most embarrassing thing you’ve ever said or done in front of someone you liked?

12. What’s the last concert you went to?

13. What food do you usually enjoy eating?

14. What was the most meaningful gift you’ve ever gotten?

15. What is your favorite childhood memory?

16. What weird smell do you find particularly appealing?

17. What are some things you wish you had known when you were younger?

18. How do you deal with people who annoy you for no apparent reason?

19. Where would you live if you could live anywhere in the world?

20. What kinds of stuff makes you laugh the hardest?

21. Do you believe in love at first sight?

22. What is the most amusing thing that anyone might spend money on or purchase on the internet?

23. What’s the weirdest thing that happened to you this week?

24. What is your pet peeve?

25. Do you like pets?

26. When was your last relationship?

27. Where is your dream travel destination?

28. What movie did you watch over and over when you were a kid?

29. When you break up with someone, how do you do it?

30. If one of my friends flirted with you, would you tell me?

31. Have you ever broken the law?

32. Do you have a mentor? What is the most important lesson they taught you?

33. Do you believe people should only date within their socio-economic status

Final Thoughts

Asking interesting questions to a guy can spark meaningful conversations that help you develop a deeper connection.

It is important to remember that effective communication is essential for a healthy relationship between boyfriend and girlfriend.

The more questions you ask, the more insight you gain into his thoughts and feelings. With these 150+ interesting questions to ask a guy, you will certainly find some to lead to intimate discussions.

Hopefully, this article has helped you discover new conversation topics with the guy in your life.

So, please consider writing us about your thoughts by commenting below.