59 Fun Questions To Ask A Guy – Make conversations interesting!

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Having all sorts of fun questions to ask a guy gives you everything a gal could need to break the ice, show interest in a guy you like, get closer with someone special, and much more.

Curiosity can be an incredibly attractive trait, so knowing what questions to ask a guy can immediately make you that much more interesting.

In a lot of ways, being a good conversation partner starts by being willing to listen, so asking questions is a powerful way to get the ball rolling with just about anyone.

Ready to get started? Take a look at our hand-selected list of fun questions to ask a guy, and you’ll never run out of options for making every conversation more fun and interesting.

Contents

11 Best Fun Questions To Ask A Guy

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These are your go-to questions, the cream of the crop for when you really want to make a fun impression on a guy. Try them out anytime you’re feeling curious about a guy, and you’ll see just how powerful they can be for making connections.

Here are the 11 best fun questions to ask a guy:

1. Where are some unusual places you’ve been to?

Tap into his flair for adventure with this question, and you just might find yourself going on one together soon.

2. What’s something you really resent paying for?

Buyer’s remorse is a common thing for just about everyone.

3. What is something that is always worth the wait?

Is he more easy-going and composed, or a bit on the impatient side? Either way, everyone has something that they’re willing to wait for.

4. What is the best way to end a long day?

Almost everybody has a “third place” — where you go between work and home. Whether it’s a bar, coffee shop, or the gym can say a lot about what sort of guy he is (and if you might be compatible).

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5. If you’re lost, do you ask for directions?

At its core, this question asks about whether he is humble enough to ask for help.

6. Do you believe that what you don’t know won’t hurt you?

Or, said another way, does he believe that “ignorance is bliss”?

7. What’s one thing you’re super passionate about?

Our passions make life interesting — both our own, as well as the lives of those around us. Asking him to share his passions with you can be an amazing way to connect on shared interests.

8. Do you prefer making plans or following along with what someone else planned?

This question asks whether he is more of a leader or a follower. Which do you prefer?

9. Can you honestly say you love what you do everyday?

If not, what could he do to change that?

10. What are the top three things on your bucket list?

A bucket list is a great indicator of someone’s biggest dreams, and this question will show you his life goals.

11. Who would you cast to play you in the movie of your life?

Does he see himself more as a tough-guy type, or the shy and sensitive sort?

8 Fun Questions To Ask A Guy To Get To Know Him

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When something about him really catches your attention, that’s the perfect time to pull out these questions to ask a guy to get to know him. A little bit more intimate, these questions inquire more deeply and specifically so you can see how compatible the two of you are as friends… or something more.

Here are the 8 best fun questions to ask a guy to get to know him:

12. What makes you smile when you get up in the morning?

You can find out whether there’s common ground for your happiness with this question, because everyone should have something in their day that makes them happy, whether it’s a perfect cup of coffee or being woken up by a beloved pet.

13. What’s one thing that defines who you are?

What we identify with can shape the whole course of our lives. Do his defining characteristics make him more or less attractive to you?

14. If there was only one cookie left, would you give it up for me?

Flirty and playful, this question is a quick way to see just how into you he might be… without coming across too strongly.

15. As a kid, what did you want to be when you grew up?

Of course things change as we grow older, but that doesn’t mean we let go of the fond memories of our first dreams as a kid; this one taps into those special memories.

via: Unsplash / Jordan Whitt

16. What’s one thing people would never know about you just by looking at you?

If he’s willing to reveal even a small secret to you about himself, that’s a definite sign of interest.

17. What has been your hardest physical challenge?

Most guys have had to endure some sort of physical hardship in their life, sometimes by choice and sometimes not. Ask this question to connect on what sort of challenges he’s overcome in his life.

18. What never fails to make you laugh?

Humor connects people, so knowing the answer to this question can give you even more ways to get to know each other.

19. What was your first cell phone?

This one is an absolute throwback! And a great way to bring up pleasant feelings of nostalgia.

7 Fun Questions To Ask A Guy You Like

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So, you’re definitely interested in him — now you need some questions to ask a guy you like. Keep it fun, flirty, and just a little bit on the more personal side to make sure he knows you’re interested in him.

Here are the 7 best fun questions to ask a guy you like:

20. What lessons have you learned from your relationships?

Save this one for when you can tell that he’s interested in you, too: It can lead to deep, meaningful conversations about what both of you really want out of a relationship.

21. What are some of your ideas for how two people can keep a relationship strong over time?

If you really like him, it’s important to start thinking about whether the two of you might have a future together — and that requires strong skills for keeping a relationship strong and healthy.

22. If I asked you to cook me dinner, what would you make me?

Being a good cook can be very attractive; does he want to show off for you?

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23. Who has been the biggest influence in your life?

The people we look up to help guide and shape our lives, so knowing who his biggest influence is can tell you a lot about the deeper parts of his character.

24. What’s one thing about the opposite sex that you’re attracted to?

When you ask this one, if he replies with something that’s related to you, it’s an obvious sign of interest… and an invitation to continue getting to know each other even more.

25. Would you date two girls on the same day?

Questions like this help you to know whether you’re on the same page. Do you both want committed relationships, or is this more of a casual dating sort of vibe?

26. Have you ever been jealous?

Let’s face it: jealousy can happen to all of us. It’s important to know whether the two of you match up on how strongly you feel about jealousy.

9 Fun But Also Funny Questions To Ask A Guy

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Sometimes the mood is just right to stay away from the serious stuff, and embrace your comedic side with some fun but also funny questions to ask a guy.

Here are the best 9 fun but also funny questions to ask a guy:

27. What’s one silly, little-kid item that you still have somewhere hidden in your room?

Asking about his mischievous, childish side can open the door to all sorts of fun and funny conversations.

28. Have you ever farted in an elevator?

I mean, I’m pretty sure everyone has… So this one is more asking whether he’ll admit to it!

29. What do you automatically think of when you smell coffee?

Smell and memory are intimately linked, so even just asking this question is a surefire way to spark some interesting memories.

30. Have you ever watched Twilight?

Twilight is such a love-it-or-hate-it movie that just about everyone has strong opinions on it — which can lead to fun and funny joking about the whole thing.

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31. Can you make pancakes?

Random and quirky, sure — but it also gives you an idea of whether you might end up cooking for each other some day.

32. When was the last time you used YOLO as an excuse to do something?

“You Only Live Once” can be a call to throw caution to the wind and do whatever hilarious thing comes to mind first.

33. Have you ever put on makeup?

Bonus points if you ask to see pictures of it!

34. What is your grossest habit?

If he’s willing to share this, be sure and give him a little bit of teasing for just how gross it is!

35. If there were only one condiment in the world, what would you like it to be?

Mustard, mayo, and ketchup might have to battle it out to see what his favorite is.

8 Fun Interesting Questions To Ask A Guy

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One of the best ways to make sure that guys will want to keep talking to you is to come off as fun and interesting with the questions you ask. You can use our curated list of interesting questions to ask a guy to make sure that you’ll never be accused of being boring.

Here are the 8 best fun interesting questions to ask a guy:

36. Where would you like to move?

Travel is one of life’s most fun and interesting pursuits, and can provide insight into what he likes doing most.

37. What’s is one thing that you’re proud of?

It’s a question that gives him an opportunity to boast a little, and also show off his good side.

38. How many phones have you broken or lost?

This gives you two a chance to cringe together at who is more of a klutz.

39. What’s your go-to alcoholic drink?

Ask this one if you want a great excuse to go out for a drink together.

40. Have you ever been to a palm reader?

And if so, did you believe what they told you?

via: Unsplash / Kristina Flour

41. Have you ever made a decision that changed your entire life? If so, what was it?

This conversation can be deep, and really tell you a lot about whether he is willing to take responsibility for his life.

42. What fictional character do you relate to the most?

Choosing a character will always show more of how he sees himself, even in non-obvious ways.

43. What is your love language?

There are 5 of them — do you know yours?

7 Fun Random Questions To Ask A Guy

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Sometimes you just need to throw caution to the wind and go for the most random questions to ask a guy. Whatever happens next, it’s guaranteed to be interesting!

Here are the 7 best fun random questions to ask a guy:

44. What’s your favorite word?

No wrong answers on this one!

45. What annoys you the most?

Everyone has a pet peeve, so you can be sure that he’ll have a good answer for this one.

46. What unusual thing do you like to do in your time off?

Because underwater basket weaving is a thing, you know.

47. Do you own a suit?

A great follow-up is to ask them “when was the last time you wore it?”

via: Unsplash / Ruthson Zimmerman

48. Do you have a green thumb?

Is he an expert gardener, or barely able to keep a houseplant alive?

49. What was the last thing you searched for on your phone?

… And incognito windows count, too!

50. What’s the craziest thing you’ve done while under the influence of alcohol?

Because everybody has one of those stories!

9 Fun But Deep Questions To Ask A Guy

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When you’re really feeling that spark of connection, that’s the perfect time to look for deep questions to ask a guy. The more time you spend together asking these sort of questions, the deeper your vulnerability and connection to each other can grow.

Here are the 9 best fun but deep questions to ask a guy:

51. What’s one mistake you wish you could redo?

Everybody makes mistakes, so this question always gives the two of you common ground to have a conversation about.

52. Are women equal to men?

The gender divide can be a huge deal, and this question gets right to the heart of how he feels about women in general.

53. What do you think is the biggest problem in the world today?

Their answer will tell you a lot about what’s most important to them.

54. What goal do you think humanity is not focused enough on achieving?

Human potential is amazing — some say limitless. What does he think is the biggest priority for people everywhere?

55. Is there something that you would not allow someone to know about you?

This powerful, direct question lets you know whether his life is an open book, or whether he is the secretive type.

via: Unsplash / Debby Hudson

56. What are your personal goals?

Personal goals are a sign of responsibility and commitment to self-improvement, two very desirable characteristics in a guy.

57. How do you tip?

The way a guy treats servers and bartenders says a lot about how he treats people of all economic backgrounds.

58. If you had to lose one of your five senses, which would you give up and why?

A great follow-up question: Which sense would you absolutely not give up, and why?

59. What helps you stay positive when everything seems to be going wrong?

Tough times really show peoples’ deeper character.

How To Pick The Best fun Questions To Ask A Guy

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Still a little confused as to how to pick the best fun questions to ask a guy? Try these four simple steps:

Step #1: Have a Variety of Questions Ready-to-go

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Try it like this: Pick at least one question from each category, practice them a few times out loud, and you’ll be more likely to come up with the right question naturally.

Step #2: Consider the Context of Your Location

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It always helps to keep in mind where you’re at. Loud, funny questions aren’t any good for a library… But a loud club at 2 a.m. isn’t the best place for deep questions, either!

Step #3: Choose Something You’re Genuinely Curious About

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Sincerity goes such a long way in getting to know somebody — so listen to your intuition, and choose the questions that are most genuinely interesting to you.

Step #4: Personalize the Question

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When you’re thinking about how to phrase the question, try to include the person’s name, and maybe reference to how you think it applies to something you already know about them.

Downloadable List of Fun Questions To Ask A Guy

Here is a downloadable list of Fun Questions To Ask A Guy (right click the image and select Save Image As…):

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More Great Ways To Talk to Guys

Looking for even more great ways to talk to guys? This list is an awesome place to start, but it’s always a good idea to be prepared for anything.

We’ve got you covered:

1. 1. Feeling that special spark, but don’t quite know what to do next? Check out our article on how to ask a guy out.
   2. Or maybe you’ve got some good material here, but still don’t feel comfortable making the first move? Try out our page on how to start a conversation with a guy!
   3. Going strictly electronic with your questions? You’re definitely going to need to know how much communication is the right amount. Study up on should I text him, and you’ll get it just right.

In Conclusion

You have so many great, authentic, and fun questions to ask a guy now — so go with your gut, and you’ll figure out the perfect one for each situation!

No matter which of these options you choose, having plenty of questions to ask a guy will always leave you well-prepared for whatever comes up in conversation. Be yourself, do what comes naturally, and you’ll definitely find the success that you’re looking for.