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180+ Interesting Questions To Ask A Guy And Start The Conversation

180+ Interesting Questions To Ask A Guy And Start The Conversation

Are you looking for some interesting questions to ask a guy? Do you need a good conversation starter that will keep the communication flowing for hours?

If you’re tired of the pointless small talk that leads nowhere, then you’ve come to the right place.

No one wants to be a participant in a boring chat that has nothing to offer. You talk about the weather until you cover all of the seasons. There’s nothing amusing about that.

Instead, you want to lead an engaging dialogue with a guy you like. You want to have fun with him while learning more about what he’s actually like.

You want to experience that feeling of time flying so fast, even though you’ve been talking for hours. That’s the kind of conversation you want to be a part of.

But sometimes, you run out of questions you can use as conversation starters. You’re all out of ideas on what to ask the guy next. So, you go round in circles, talking about the same things, repeating “how was your day” as if there’s nothing else to talk about.

That’s why you need to read through our list of super interesting questions you can ask a guy. There’s something for every stage of a relationship.

Whether you’re still getting to know each other or you’ve been together for a while, here you can find something that works for you. No more dry and monotonous conversations once you start incorporating these questions!

Interesting questions to ask a guy while still getting to know each other

The beginning of your journey together can be daunting. Also, it can be particularly difficult to find a way to keep the conversation fun when you don’t yet know much about each other.

You don’t want to ask him something too personal and scare him away before he even has a chance to get to know you better. But you also don’t want to hit him with the same old boring questions everyone keeps asking at the start of a relationship.

“What are your hobbies?” and “What do you do for fun?” aren’t really the kinds of generic topics you want to talk about.

Instead, you want something fun, engaging, and different. Something that lets him talk freely and at the same time enables you to learn a lot about him by the way he answers.

We’ve got exactly what you need right here. Try out some of these fun and interesting questions you can ask the guy you’re just starting to get to know.

1. What movie would you like your life to be more like?

2. Do you have a useless talent? Something only you can do even though there’s no point in it?

3. What’s something risky you did that paid off in the end?

4. Is there a movie you could watch till the end of your life?

5. Did you ever dream about building a tree house?

6. What’s something you used to love doing as a kid but now think it’s lame?

7. Is there something you would never do, even if someone paid you a million dollars?

8. What’s something you were worried about but it turned out fine in the end?

DONE! 180+ Interesting Questions To Ask A Guy And Start The Conversation

9. Is there something you’re tired hearing about?

10. What’s your field of expertise? Something you know a lot about and always want to learn more?

11. Do you think that there are any double standards that need to be ended?

12. What’s the one cause you would dedicate your life to if you had to choose?

13. What’s something people complain about all the time?

14. Do you think there’s one question you can ask anyone to find out a lot about them?

15. Is there something you thought to be silly but once you tried it, you changed your mind?

16. Who’s your favorite author?

17. Tell me your most fun experience! Something that made you stop for a second and realize that you’re having a great time.

18. What’s something you always have time for?

19. Tell me two things you would never spend your money on.

20. What was your favorite cartoon growing up?

21. If you had an opportunity to level up in life and improve something about yourself, what would you use your skill points for?

22. What’s the most boring sport you’re not into at all?

23. Is there a game you always lose at?

24. Is there something you enjoy doing but others see it as too feminine?

25. What’s the weirdest food you loved eating as a child?

26. What’s one skill you would love to master?

27. Where would you move to if you could?

28. What’s one of your earliest memories you can recall?

29. If your house was on fire, what’s one thing you would want to save from the flames?

30. Do you have a weird flavor combination you enjoy?

31. Where have you traveled so far and what does your dream vacation look like?

32. What’s the worst thing you ever tried?

33. Have you ever experienced paranormal activity?

34. Is there a fun experience you had but won’t ever do again?

35. What’s the funniest joke you know?

36. Do you have a creative outlet?

37. What’s your “back in my day” story?

38. What’s your favorite part of the day?

39. If you had to be certain age for the rest of your life, what age would you choose and why?

40. Would you ever travel to the foreign country on your own?

41. What’s the most attractive trait a woman can have?

42. What three words would you use to describe yourself?

43. What is something that says a lot about the person you’re dating?

44. What did you want to be when you were a kid?

45. If you could travel back in time, which historical period would you choose?

DONE! 180+ Interesting Questions To Ask A Guy And Start The Conversation

46. What’s your comfort meal after a rough day?

47. Do you believe in love at first sight?

48. What’s your favorite holiday?

49. Is there something you hate about technology?

50. What’s the worst job you ever had?

51. What do you think – are you an extrovert or introvert?

52. What would you never allow someone else to do to you?

53. Where do you wish to see yourself in a year’s time?

54. Do you think that your zodiac sign accurately describes you?

55. What’s your preference: a good book or a good movie?

56. When was the last time you laughed so much your stomach hurt?

57. What type of person are you: ten minutes late or ten minutes early?

58. Do you play by the rules or do you believe that rules are made to be broken?

59. Do you go with the flow or do you need to organize your time first?

60. How well do you work under pressure?

61. Do you believe in karma?

62. What’s something that always makes you laugh?

63. How do you think others would describe you?

64. If you could live anywhere in the world, where would you want to go?

65. What’s something that makes you feel relaxed, even though you’re highly tense?

66. What item could you never live without?

67. What’s your biggest pet peeve?

Interesting questions to ask a guy if you’ve been dating for a while

If you’ve been dating for a while, you may start to feel like you’re running out of topics. As if you’ve already covered all the conversations you could have.

But don’t worry, as there’s always something to talk about. You may think that you’ve heard it all, but trust me, there are many more things you can learn about your partner.

Here are some interesting questions you can ask a guy, even if you feel like you know everything about him.

They’re suitable for couples who have been together for a while and know a lot about each other. Since their relationship is already strong, they tend to be more open about serious questions that are usually avoided at the very beginning of a relationship.

Here’s what you could ask him to jazz up your regular chats.

1. What’s the most stressful situation you had to go through in your life?

2. What three events affected you the most and shaped you into who you are today?

3. What’s your greatest achievement? Something you’re proud of?

4. Is there anyone you met throughout your life who left a great impression on you?

5. What story from your life will you always keep retelling to your children and even grandchildren?

6. What does friendship mean to you and do you have a friend you can trust with your life?

7. What’s the best decision you made that started off as the wrong one?

DONE! 180+ Interesting Questions To Ask A Guy And Start The Conversation

8. What is something someone did for you that made your life better?

9. What should a real man be like? Do you think that society sets the bar way too high?

10. What do you suck at so bad, to the point you’ve given up on it completely?

11. What always makes you angry even though there’s no particular reason for it?

12. Is there something that annoys you when others are doing it but you occasionally do it as well?

13. What’s your most useful skill?

14. What random compliment have you received that’s still stuck in your memory?

15. What do you believe we all should be doing on a daily basis that would improve our lives for the better?

16. Do you ever judge people even though you know it’s wrong?

17. What’s the worst injury you’ve ever gotten?

18. Have you ever gone through something that ended up being worse than you imagined it to be?

19. What simple thing makes you unexpectedly happy?

20. Is there a motto that keeps you going?

21. What does the exact opposite of you look like?

22. What piece of advice you would give everyone because it can change their life?

23. What’s one good thing you learned this year that will stay in your memory forever?

24. What wrong assumption do people have about you?

25. Do you have a role model?

26. What’s your favorite thing about being in a relationship?

27. What pick-up line has never worked for you?

28. Is there something that makes you smile, even on your bad days?

29. What’s the nicest thing you’ve ever done for someone?

30. What’s your favorite place to go to, to clear out your thoughts?

31. Do you see yourself as a parent?

32. What’s the biggest trouble you’ve found yourself in?

33. How do you know that it’s the right time for a woman you’re dating to meet your family?

34. Are you a competitive person?

35. What song always reignites an old memory?

36. Is there something you always wanted to do with your girlfriend but you never had a chance to do it?

37. How do you act when you like a woman a lot?

38. What does a healthy relationship look like from your point of view?

39. What would you tell to your younger self?

40. What advice do you always give to friends who are going through a breakup?

41. What’s something you always procrastinate on?

42. How would you describe me to someone who doesn’t know me?

43. Do you have a New Year’s resolution you always make yet always fail to achieve?

44. How many serious relationships have you had?

45. What do you expect from your partner?

46. Do you believe in soulmates?

47. Do you follow your head or your heart when making decisions?

48. Do you believe that love can overcome all obstacles?

49. What’s one thing no one knows about you?

50. Is there anything you’re superstitious about even though you know it’s irrational?

51. If you had three wishes, what would they be?

52. Do you have a dream that keeps repeating itself, over and over again?

53. How do you figure out if you can trust someone?

54. What have you learned about yourself from past relationships?

Interesting questions to ask a guy to deepen the bond

Sometimes, you’re desperately looking for some interesting, thought-provoking questions you can ask a guy when you’re trying to strengthen the bond between the two of you.

You want him to feel like he can trust you and share personal details with you. But then again, you don’t want to be too nosey and ask him something he’ll be uncomfortable to answer.

These questions are a perfect balance between the two, and you can use them to create a stronger connection between you and your partner.

1. What’s your biggest insecurity?

2. What’s something you hate with all your guts?

3. What’s something you daydream about all the time?

4. Is there something you need to get off your chest?

5. Is there a movie that made you cry?

6. What’s something we all should experience at least once in our lives?

7. What are the two things you’re most passionate about?

8. Do you believe there’s some things you have to experience in order to learn how to appreciate them?

9. What have you really wanted to do for a long time but still haven’t done it?

10. If you could pack your things and leave the city to have a fresh start, would you be willing to do it?

11. Have you ever felt as if you don’t belong anywhere?

12. What’s something you regret doing?

13. What’s the most important thing you’ve done in your life?

14. Do you remember your most embarrassing moment?

15. What’s your favorite compliment you always feel happy to receive?

16. Is there something you’ve never told anyone?

DONE! 180+ Interesting Questions To Ask A Guy And Start The Conversation

17. What do you like the most about me?

18. What’s something you’re afraid of?

19. If you could relive one moment in your life, which one would it be?

20. Have you ever been betrayed by a close friend?

21. Are you closer with your mom or dad?

22. Is there something that happened to you unexpectedly and you hated it at first, but then it proved to be the best thing in your life?

23. Who’s the most important person in your life?

24. What’s the most meaningful gift you’ve ever received?

25. Is there something that always takes you back in time?

26. What makes you stay positive, even when everything around you is falling apart?

27. Have you ever been cheated on, and if so, how did it made you feel?

28. Have you ever broken someone’s heart?

29. How do you deal with people you don’t like yet have to keep seeing on a daily basis?

30. What’s your biggest regret?

31. What’s something you often take for granted?

32. What’s your guilty pleasure?

33. Do you remember any particular moment when you stepped out of your comfort zone and had the time of your life?

34. What are your goals for the future?

35. Did you have a happy childhood?

36. What are your expectations from a romantic relationship?

37. What’s the worst thing you’ve ever done?

38. Have you ever done something brave that still makes you proud to this day?

39. What was the happiest day of your life?

40. Do you think there’s something that’s worth the wait?

41. Do you believe in destiny and that everything happens for a reason?

42. Is there something you would do right away if you knew that no one would judge you?

43. If you had to wake up one day and not feel fear, what would you do first?

44. If you could make one wish and know it would come true, what would you wish for?

45. What was the most difficult period of your life?

46. Is there a mistake you made in the past that you’ve promised never to make again?

47. What’s something you do that makes you feel alive?

48. What’s the biggest lie you ever told someone?

49. Is there something you always look forward to?

DONE! 180+ Interesting Questions To Ask A Guy And Start The Conversation

50. Is there anything standing in the way of achieving your goals?

51. Is there an opportunity you didn’t take and now you regret that decision?

52. Do you have a memory that you would love to erase from your mind?

53. Have you ever told a lie and it backfired on you?

54. What are you most grateful for?

55. Who’s that one person you go to every time you need advice?

56. Have you ever been in love?

57. What’s the best thing about your life right now?

58. If you could change anything about your past, what would it be?

59. Have you ever lost someone who means a lot to you?

60. What scares you the most about your future?

61. Have you ever succeeded at something you never thought you could? How did it feel?

62. Who in your family are you the most similar to?

63. What’s one thing you want to accomplish before you die?

I hope this was helpful and you were able to find plenty of interesting questions to ask your guy. As long as there’s no awkward silence and the conversation is moving forward, you’re golden.

And I’m sure that these questions will turn all those quiet moments into ones filled with nonstop chatter.

Good luck with your relationship and I hope that things will turn out even better than you planned them to! Fingers crossed it all works out great!

180+ Interesting Questions To Ask A Guy And Start The Conversation