180 Intriguing Questions to Ask a Guy To Deepen Your Connection

Once you get us started, we’ll probably talk your ears off about all the things we love (like English soccer, for me). Stereotypically speaking, however, I’ll admit that we guys aren’t always the best at speaking up about ourselves, our histories, and our emotions. This means that getting a conversation started with a guy can be a challenge—sorry!—but there are a lot of fun, funny, and functional questions you can ask us that we’ll enjoy answering.

These kinds of questions for guys can help to get us warmed up and get the chatty ball rolling over dinner, coffee, or at work. Soon enough, you’ll know everything about us, from our favorite TV shows to what food we’d be happy to eat every single day, where we dream of visiting, and, more importantly, how we like to show and receive love.

We’ve got a slew of great questions to ask guys—from flirty questions for the guy you think is cute to questions that will help you get closer to your bestie as well as plenty of ice breakers to crack open your partner and some questions for learning more about your male co-workers, and just about every other scenario imaginable, too! Here are 180 questions to ask guys to get the conversation started and keep it going strong whenever you hit a lull.

Questions for Guys about Love, Dating, and Relationships

1. How do you flirt?

2. Are you comfortable making the first move?

3. What does love look, mean and feel like to you?

4. What’s your type?

5. What are you like as a partner?

6. What’s the best relationship advice you’ve ever heard?

7. How do you show love?

8. How do you like to receive love?

9. What’s your most successful pick-up line?

10. What’s the worst pick-up line you’ve ever heard (whether you used it or not)?

11. Have you ever been in love?

12. What’s the longest relationship you’ve had (and what made it last that long)?

13. What's your ideal first date?

14. What's your biggest turn-off?

15. What's your brightest relationship red flag?

16. What would you do if someone cheated on you?

17. How do you know when to introduce a new partner to your family?

18. What kind of relationship are you looking for?

19. What part of my body are you most interested in?

20. What is the one personality trait that's the most important to you in a partner?

21. Where is the strangest place you've ever kissed?

22. What’s the most unusual place you’ve taken a date?

23. Describe the most romantic vacation you’d like to take with me.

24. How would you describe me in only three words?

25. Have you been able to stay friendly with any of your exes?

26. How does it make you feel when people flirt with you?

27. What would you cook me for dinner?

28. How do you make the first move?

29. Do you believe in soul mates or love at first sight?

30. What's your definition of a healthy relationship?

31. How did your last relationship end?

32. Would you hold me if I’m afraid during a scary movie?

33. What question do you always ask on a first date?

34. What’s your favorite way to ask someone out?

35. When will you finally ask me out?

36. What do you think is the key to a successful, long-term relationship?

37. What are three words that describe you as a romantic partner?

38. What's the kindest thing you've ever done for a partner?

39. What's the nicest thing a partner has ever done for you?

40. What would be your pet name or cute nickname you’d give me?

Funny Questions for Guys

1. If you could only wear one color for the rest of your life, what would it be?

2. What is the funniest movie you have ever seen?

3. Which actor would play you in a movie about your life?

4. Who would play me in that same movie?

5. Everyone knows that potatoes are the most versatile food, what’s your favorite way to enjoy them?

6. How are you going to survive a zombie apocalypse?

7. What’s your most unusual habit?

8. Which dinosaur is your favorite?

9. Not including a wish for more wishes, if you had three wishes, what would they be?

10. What’s the most useless invention of all time?

11. What's the grossest thing you've ever eaten?

12. What’s the funniest name for a WiFi network you’ve ever seen?

13. Are you afraid of clowns?

14. Who’s more annoying, a mime or a magician?

Questions to Ask Guys over Text Message

1. How was your day?

2. What’s the best thing that’s happened to you this week?

3. What’s your favorite gif?

4. What emoji makes you think of me?

5. What are the last five emojis you used?

6. How would you describe me to your friends over text?

7. How would you describe me to your family in a text message?

8. Do you like texting or talking on the phone?

9. What are your favorite kinds of conversations?

10. What three words sum you up perfectly?

11. What is the most radical opinion you have?

Personal Questions for Guys

1. When was the last time you cried?

2. What makes you emotional?

3. What's something you struggle with?

4. What does "being a man" mean to you?

5. What are you most proud of?

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

7. Do you have any regrets?

8. What's your favorite part of your own body?

9. What's the best part of your average day?

10. Do you like to take naps?

11. What’s your favorite recipe/thing to cook?

12. What’s something most people don’t know about you?

13. What would be the title of your memoir?

14. How do you define being a “good” person?

15. What are you most proud of?

16. Are you or have you ever been addicted to anything?

17. What do you wish you had more time for?

18. If you had to give a 30-minute talk with no time to prepare, what would be the subject?

19. Do you snore?

20. What does your bedtime routine look like?

21. How do you sleep: back, side, stomach?

22. What's your favorite childhood memory?

23. What's the most important lesson you ever learned?

24. Who's been the biggest influence or inspiration in your life?

25. What does family mean to you?

26. When are you most happy?

27. What's your biggest goal or dream you're still working to achieve?

28. What's the best piece of advice you've ever received?

29. If you could instantly change one thing in the world, what would it be?

30. What cause do you care about the most?

31. How do you express yourself creatively?

32. What did you want to be when you grew up?

33. Who is the most important person in your life?

34. What's your biggest pet peeve?

35. If you could re-do one moment in your life, what would it be?

36. What's your favorite thing about your group of friends?

37. What was the last thing that made you cry?

38. What's the worst injury you've experienced?

39. What is something that never fails to make you smile?

40. What’s your favorite charity to donate to?

41. What’s the best aspect of your personality?

42. Who’s your emergency contact?

43. What does happiness mean to you?

44. What was the last brave thing that you did?

45. What’s your finest moment as a human being?

46. What is a moment that you bungled and how did you recover from it?

47. What’s your greatest fear and did you ever face it?

48. What do you hope your legacy is at the end of your life?

49. What would you change about your childhood?

50. Where or when do you feel the most safe?

51. How do you handle being angry, stressed, frustrated, or disappointed?

52. Who is your favorite member of your family?

53. What would you tell your younger self?

54. When was the last time you were really sad? What cheered you up?

Pop Culture Questions for Guys

1. What's your all-time favorite movie?

2. What was your favorite cartoon as a kid?

3. What do you geek out about the most?

4. What's the last movie you watched?

5. What movie are you most excited to see next?

6. What's your comfort TV show that you could binge-watch again and again?

7. What's your all-time favorite band or musical artist?

8. Who's in your Spotify Top 5 right now?

9. What social media site do you spend the most time on?

10. What are you reading these days?

11. What’s usually better, the book or the movie/tv show?

12. What book do you think should be turned into a movie or TV show?

13. Do you collect anything, like vinyl records or Pop figures?

14. Which Ted Lasso character is the most intriguing and why?

15. Who’s your favorite comic book character?

Icebreaker Questions for Guys

1. What's your favorite thing in your kitchen? Why?

2. What’s the funniest nickname you’ve ever been given?

3. If you could eat one food every day, what would it be?

4. What is your favorite place to visit?

5. If money were no object, where would you travel to right now?

6. If you won the lottery today what's the first thing you'd buy or do?

7. Do you have a favorite quote?

8. What are your hobbies?

9. What's one thing you would change about yourself?

10. Which superpower do you wish you had?

11. What's your favorite animal?

12. What do you like to do on a day off?

13. What's your favorite charitable or volunteer work to do?

14. Which is better, cats or dogs?

15. Which is better, a beach day or hike in a forest?

16. What's your favorite season?

17. Which sport is your favorite to watch?

18. If you could have dinner with three people, living or dead, who would they be?

19. If you were forced to enter a talent show, what would your talent be?

20. What's the purchase you regret the most, and why?

21. What's your favorite animal?

22. Which five countries are at the top of your travel bucket list?

23. Do you think zodiac signs accurately predict personalities?

24. Are you a competitive person?

25. What's one thing you think everyone should do or experience at least once in their life?

26. If you could meet any one of your heroes, which one would you choose?

27. Which movie villain do you think is misunderstood?

28. What’s your go-to coffee shop order?

29. What’s your favorite Halloween costume?

30. Aside from sliced bread, what do you think has been the most significant invention of all time?

31. Describe your perfect slice of pizza? Toppings, thin crust, etc.

32. Are you always hot or cold?

33. What’s your favorite piece of clothing you own?

34. What’s the first thing you do every single morning?

35. What’s the funniest joke you’ve ever heard?

36. What’s the best compliment you’ve ever received?

37. What’s the best compliment you’ve ever given?

38. What’s your guilty pleasure food?

39. What's your biggest phobia?

40. What would you never spend money on no matter how much money you had?

41. What do you love most about your favorite restaurant?

42. What’s your most prized possession?

43. What’s your order at the bar: beer, wine, shots, cocktail or mocktail?

44. What age has been your favorite so far? Why?

45. What was the most historic thing you witnessed or took part in?

46. What’s your favorite holiday? What do you love most about it?

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

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