fun questions to ask a guy

Here’s why you’re looking for questions to ask a guy you like:

You know you really like this guy.

You want to get closer to him or just have a good conversation.


What to do when you run out of things to talk about?

And what can you ask over text, to keep a conversation going with the guy you like?

Fun questions can be the perfect ice breakers and conversation-starters and are guaranteed to make you two smile and have a good laugh together.

Here are 88 fun questions to ask a guy, in any situation.

These questions can be more than just fun, they can unlock some secrets, they can tell you a lot about your crush, and they can strengthen your bond faster than you’ve ever imagined.

(Not sure if he is serious about you? Here’s how to find out now)


Fun Questions to Ask a Guy (In Person)

questions to ask your crush

The secret to having a great conversation is to ask open questions (as opposed to yes/no questions) and to answer them yourself after your crush has answered.

Just one of these questions can lead to a good 30 minute conversation, full of smiles and giggles, which will instantly get you closer to your crush.

1. What would you do if you could be invisible for one whole day?

2. What’s the funniest way a girl has asked you out?

3. What was your first date (ever) like?

(Read: How to Write the Best Online Dating Profile)

4. What’s the worst lie you ever told? Did you get caught?

(Read: Why Men Lie to Women)

5. If you could change anything about you or your life, what would you change now?

6. If you could change one thing in your past, what would you change?

7. If you could change your name to anything in the world, what would you change it to?

8. If you could take a girl to anyplace in the world, where would it be?

9. What body part would you change on yourself if you could?

10. If your house was on fire and you could only save one thing, what would it be?

11. Can you fake any accent? If yes, would you show me?

12. What is the best sports stadium/arena you have been to?

13. What’s the last thing you argued with your parents about?

14. Are you planning on studying after Year 12?

15. Do you ever eat food that’s been dropped on the floor?

(Btw, if you have no clue whether this guy is into you at all, here’s how to know if he likes you.)

Fun Questions to Ask Over Text

text questions to ask a guy you like

When you try to talk to a guy through text, asking him questions like “what’s your celebrity crush and why” is a big no-no.

Starting a conversation over text, in a manner that would seem natural, has to start with “current affairs” (the latest news, reality show happenings etc).

(See how to flirt with him over text HERE)

Text is not the place to ask him how many times he checks himself out naked in the mirror every day.

1. What’s your favorite sport and sports person?

2. What’s the weirdest text you’ve ever received from a girl?

3. Tell me the truth…how many selfies do you have on your phone?

4. What’s your favorite store you like to go to?

5. What’s your least favorite class/teacher?

6. What do you do when you’re bored?

7. I’ve just finished doing…(this and that). What are you up to?

8. Did you ever get dumped over text?

9. If you find 0 on the floor right now, what would you do with it?

10. What’s your favorite reality show?

11. Do you think you could give up technology for a week?

12. What’s the most-played song on your iPod?

13. What’s the lamest joke you’ve ever heard?

14. Would you prefer a day at the beach or a movie marathon?

Fun Question to Ask on a Date

fun questions to ask a guy on a date

I always advise to not get into “heavy” conversations on the first few dates. Resist the temptation to ask a guy about his past relationships, what his ex like is, and what’s his favorite porn.

Keep it casual, funny and light. Here are some fun questions to ask a guy on a date:

1. If you could be a woman for one day, what would you do in that day’s time?

2. If you could commit any crime and get away with it, what would it be?

3. If your life was turned into a movie, what actor would play you?

4. Do you have any enemies?

5. If you could be any super hero, who would it be?

6. If you could travel through time and meet yourself when you were a kid, what would you say?

7. Are you happy being single?

8. Would you rather have true love or win the lottery?

9. What’s your idea of a perfect day? / If today was the last day of your life, how would you spend it?

10. Would you rather be smart and ugly or dumb and beautiful?

11. Ever had a rumor spread about you?

12. What movie deserves a sequel?

13. If you could lock up one person in a mental institution, who would it be?

14. What would you refuse to do for one million dollars?

15. If fat, calories, cholesterol, etc were not an issue, what two foods would you feast on?

16. Can you cook?

17. What household chore have you never done?

18. Who is your most admired athlete of all-time?

19. What animal or insect disgusts you the most?

20. Are you a nice drunk or a nasty drunk?

21. If you could be a member of any TV-sitcom family, which would it be?

22. If you had to dispose of a dead body, how would you do it?

23. Where is the farthest place you ever traveled in a car?

24. What was the first job you ever had?

25. Have you ever cheated on a test?

26. Can you touch your nose with your tongue?

27. What radio station do you turn to when you are in the car?

28. Have you ever been punched in the face? Why?

29. Have you ever broken a bone? How?

30. What is your most visited website?

31. Have you ever been on a diet?

32. If you could work for anyone you choose, who would it be?

33.  Are you closer to your dad or your mom? Why?

34. Who was your first crush?

35. What’s the meanest thing you’ve ever done to someone to get back at them?

36. Do you save money or spend it?

37. What makes you really sleepy?

38. What is the nicest thing someone else has done for you?

39. What would you do if you didn’t like your mate’s new girlfriend?

40. What’s at the top of your post-school bucket list?

Be sure to check out my post about the worst dating mistakes women make, and how to avoid them.

Flirty/Intimate Questions to Ask a Guy

flirty questions to ask a guy

These questions are appropriate only if you’re already dating the guy, or you feel comfortable enough around him.

1. What is the worst thing that somebody has walked in on you doing?

2. What is your biggest turn on?

3. What’s the craziest place you ever had sex?

4. Have you ever cheated on your partner? Did this person ever find out, and if so, what happened?

5. How often do you examine your naked self in the mirror?

6. Name a place on your body where you are most ticklish?

7. Would you kiss a girl on the first date?

8. Ever tried online dating? Worst experience?

9. How would you feel if your girlfriend had a guy best friend?

10. If you had to make out with a friend of the same sex to save the world from aliens, whom would you pick?

11. If you had to explain about the birds and the bees to a child, let me hear how you’d go about explaining it to them?

12. What is the one thing a woman should never do?

13. What is the first thing you do when you get out of bed?

14. What’s under your bed?

15. What do you wear to bed?

16. Would you consider yourself obsessed with anything/anyone?

17. Have you ever been stood up?

18. Have you ever broken someone’s heart?

19. Ever been in love with 2 people at the same time?

20. What is the best compliment you have ever received?

21. Who would you want to be tied to for 24 hours?

This concludes my ultimate list of fun question to ask a guy.

Did you know?

One of the best ways to flirt with a guy over text is to play the classic game of embarrassment – Truth or Dare!

Here’s my list of 81 flirty truth or dare questions for texting – enjoy!

I hope you find them useful and if you have any other ideas for questions, please share them with me…

And, if your next step is getting your crush to fall for you head over hills, here’s how to do it.

I’m sure I left out a few great questions, what are your ideas for questions? Share with me in the comments..

Rooting for ya,


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