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Having the right questions to ask a guy can make all of your conversations fun, engaging, and interesting. Everybody knows the feeling of an awkward silence – but do you know how easy it can be never to have those again?

If you want to feel confident and natural every time you're out socializing, using a few easily-memorized questions as a means of how to start a conversation with a guy is the perfect move. They open the door for smooth conversations that can make deep connections.

In fact, it's a little-known secret that people love people who ask questions. So take a page from business researchers, muster up your courage, and have the confidence that asking questions is a good thing.

We have everything you need to start asking guys great questions... Today!

Contents

best

Best

get to know him

To Know Him

Guy-You-Like

Guy You Like

your boyfriend

Your Boyfriend

fun to ask

Fun To Ask

funny

Funny

Interesting

Interesting

Random

Random

deep

Deep

How to pick - #How-to-pick

How To Pick

Downloadable list - #Downloadable-list

Downloadable/Printable List

More ways - #More-ways

More Ways

12 Best Questions To Ask A Guy

These powerful examples are the best questions to ask a guy, hands down. We've carefully selected only the top of the line, most successful questions to keep your connections fresh and interesting.

Here are the 12 best questions to ask a guy:

1. What do you value the most in a friendship?

It's true that a person's friendships say a lot about who they are – so this question secretly asks guys what they value most about themselves.

2. What’s your family like?

Everyone can agree that family is important, so asking about his family will reveal what is important in his life.

3. What is the most important political issue to you?

If you're feeling brave and up for an open discussion, this one always draws a good response that shows a guy's values.

4. If you could host a dinner party with four people, living or dead, who would you invite?

Questions like this give room for creative expansion and invite lots of follow-up questions as to why they chose those guests.

5. If you ever got a tattoo (or if you already have one and get another one), what would you get?

Tattoos are an incredibly personal thing and a great way to explore someone's deepest-held beliefs.

6. What’s the nicest thing someone has ever done for you?

How has someone else helped to make his world better?

7. What’s the biggest regret that you have in your life so far?

Tread lightly with this one, and you can open the door to heart-felt connections over what's not been perfect in your lives.

8. What is always worth the wait?

How patient is he, and for what things? Patience is a virtue, after all.

9. What would you immediately do differently if you knew no one would judge you?

Or, said another way, what do you keep yourself from doing because of being worried about how people would see you?

10. What do you wake up excited about?

What makes life worth living for him?

11. What’s your most embarrassing story?

Embarrassment can be an easier way to talk about potentially difficult feelings.

12. What is your dream vacation?

Once you ask this one, you can follow up on any answer by asking him to describe it in more detail.

10 Best Questions To Ask A Guy To Get To Know Him

Questions can be a great way to introduce yourself, and the right questions to ask a guy to get to know him can be used right off the bat – or saved for later in the conversation.

Here are the 10 best questions to ask a guy to get to know him:

13. What makes you insecure?

Our insecurities reveal a lot about our deeper character and how we deal with challenges.

14. Who are you closest to in your family?

Making connections to the people he knows best can bring you closer together.

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

A guy's passions will tell you about his drive and direction in life – and be a great way for him to share with you.

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

Is he more than meets the eye? What secret interests does he have?

17. What fad or trend do you hope comes back?

Nostalgia is a great conversation topic for people of similar age groups.

18. What’s something you like to do the old-fashioned way?

Camping? Shaving? What is better done without the conveniences of modern technology?

19. What childish thing do you still enjoy?

Preserving that childlike joy can be challenging, but definitely makes life more interesting.

20. What are your long-term goals?

A guy's goals will tell you what his motivations are. What makes him persevere in the face of difficulty?

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

Is he more of an outdoorsy type, or a stay-at-home guy?

22. What is your biggest fear?

A great follow up question is to ask him how that fear has changed his life, and whether he has ever confronted it.

12 Best Questions To Ask A Guy You Like

Are you feeling that spark of interest with a guy you're talking to? Knowing a few questions to ask a guy you like can be an amazing way to take the pressure off of yourself in that situation.

Here are the 12 best questions to ask a guy you like:

23. What's the most spontaneous thing you've ever done?

Getting him started talking about spontaneous things can lead to the two of you finding your own spontaneous adventure together.

24. If you had to relive one hour of your life on repeat, what hour would it be?

This question lets you know what makes him happiest.

25. What are you looking for in a relationship?

If the feeling of interest is mutual, use this question to get straight to the point!

26. How do you handle conflict in a relationship?

It's inevitable that fights happen, and how someone handles them shows a lot about their level of maturity.

27. Are You a Night Person or a Day Person?

Whether you're both night owls or early birds can be an indicator of compatibility.

28. Do You Know Any Magic Tricks?

Bonus points if you can have him teach you the trick!

29. What is your favorite food?

The classic saying that "the way to a man's heart is through his stomach" still holds true.

30. Have you ever tried online dating?

If he has, does he have any good stories from it?

31. If you could go back in time, what’s one piece of advice you’d give to your younger self?

Everybody has regrets, so this question asks what he would like to have done differently in his life.

32. Who or what has changed your life?

Asking him about how he became who he is can bring you closer together.

33. What is on your bucket list?

Then, can the two of you check one of those items off together?

34. What is your biggest strength?

What does he think his best attributes are? Bonus follow-up: Ask what his biggest weakness is, too.

6 Questions To Ask Your Boyfriend

If you're already happily in a relationship, that doesn't mean you should stop getting to know each other even better. Making a conscious effort to have great questions to ask your boyfriend can keep the relationship fresh and interesting.

Here are the 6 best questions to ask your boyfriend:

35. What about us do you think works well together? How do we balance each other out?

Reflecting on both of your positive qualities can be a powerful way to reconnect.

36. If you had one word to describe our love what would it be?

Get right to the point with a strong reminder of how much you care for each other.

37. What’s your biggest fear for this relationship?

Talking about your fears together can bring you closer together and prepare you for a future together.

38. What’s one difference between us that you absolutely love?

Celebrating your differences is just as important as enjoying your similarities.

39. What music do you like that you wish you listened to more?

Why not listen to that music more as a way to spend time together?

40. How do you think we both have changed since we first started dating?

Have those changes been for the better? Are you both growing as people?

6 Best Fun Questions To Ask A Guy

Keep things lighthearted and cheerful with these fun questions to ask a guy, and you can be sure that he'll think of you as a fun and exciting person.

Here are the 6 best fun questions to ask a guy:

41. What is your most hilarious childhood experience?

Just about everyone has a story of being funny and ridiculous as a kid.

42. Do you consider yourself a nice or a naughty person?

Afterwards, you can tease them about being on Santa's list.

43. What are you curious about?

Curiosity compels us to explore the world – a great way to encourage his creative side.

44. What is a superstition that you have?

Superstitions are a common connection between pro athletes and housewives, and a great topic to gently poke fun at.

45. What is one thing you don't know how to do, but wish you did?

After he answers, look up whether you could take a class on it together!

46. Why is there an expiration date on sour cream?

Say this one with your best poker face, then wait for the laughs.

5 Best Funny Questions To Ask A Guy

Getting a laugh out of him can be as easy as having great funny questions to ask a guy. You can practice your timing and stage presence with these funny questions.

Here are the 5 best funny questions to ask a guy:

47. Who or where would you haunt if you were a ghost?

If you've got forever in the afterlife, you might as well make it interesting.

48. If you could change a body part, what would it be?

This highly suggestive question can lead to some good laughs if it's not taken too seriously.

49. If animals could talk, which would be the rudest?

Afterwards, give your best impressions of rude animal voices.

50. What is the best pick-up line you know?

Make him entertain you with this question!

51. What songs are on your zombie killing soundtrack?

Bonus points if you can play Call of Duty together to that soundtrack.

7 Best Interesting Questions To Ask A Guy

Thought-provoking, interesting questions to ask a guy can take any conversation into new territory.

Here are the 7 best interesting questions to ask a guy:

52. What is the worst advice you have ever received?

How did that advice play out?

53. What have you always wanted to try?

Then, how can you encourage him to try that thing?

54. If you had to spend $10,000 today, how would you spend it?

Money can't buy happiness, but it's certainly more difficult to be sad in a $10,000 hot tub.

55. What’s one thing you feel like people don’t appreciate enough about you?

This question secretly asks what he thinks his best qualities are.

56. What does your perfect day look like?

The two of you can brainstorm how to make that day happen together.

57. Have you ever liked someone and never told them?

Is it true that it's "better to have loved and lost, than never loved at all?"

58. What’s the nicest compliment you’ve ever received?

Guys don't often receive compliments, so this one can bring up great memories.

6 Best Random Questions To Ask A Guy

These random questions to ask a guy are perfect when you're not sure where the conversation is going, but want to keep talking.

Here are the 6 best random questions to ask a guy:

59. If you started a business, what type of business would it be?

Does he have an entrepreneurial side?

60. If you could learn the answer to one question about your future, what would it be?

What is he most curious about the outcome of?

61. What, if anything, is too serious to be joked about?

Is anything "off limits"? What are the boundaries of his humor?

62. What’s the craziest thing a boss has ever asked you to do?

Work life can get very strange, indeed.

63. What was your first favorite movie, as a child?

Then, can you find that movie to watch together?

64. What’s a recurring dream you have?

Dreams have been a source of curiosity for millennia. What does he think the dream means, too?

7 Best Deep Questions To Ask A Guy

Deep questions to ask a guy bridge the gap between surface-level politeness and the possibility of genuine connection. They're especially good to ask when you feel the start of a great connection, and want to see where it might go.

Here are the 7 best deep questions to ask a guy:

65. What was your favorite place to go as a child and why did you love it there?

Getting into talks about childhood memories can bring up deep connections to time and place.

66. When you think about the future, what do you imagine?

How does the future he's imagining line up with yours? How is it similar and different?

67. Who was your first girlfriend?

What memories does he have from this young love?

68. What are your biggest weaknesses?

How someone handles their life's challenges says a lot about their true character.

69. Do you believe in reincarnation?

The religious world might be divided on this topic, but when someone believes in it, they feel strongly about it.

70. What thing about the future scares you the most?

Sharing fears can be a powerful way of coming together over shared vulnerabilities.

71. Do you wish you were raised differently?

Any question that asks about the past, and childhood in particular, can be a powerful way to inquire deeply about his life.

How To Pick The Best Questions To Ask A Guy

Picking the best questions to ask a guy can be simple and easy with these three steps.

Here is how to pick the best questions to ask a guy:

1. Check out your setting

Consider where you're at, what other people you're with, and how much time you have to talk before deciding on the best questions to ask.

In other words, the best questions for an intimate date at a coffee shop will be totally different from the best questions to ask at a loud, crowded concert.

2. Make it personal

Be sure to introduce yourself before you start asking questions.

Then, use his name when you're asking the questions – it makes it feel personal and genuine.

3. Trust your intuition

Maybe most important of all... Don't overthink it! 

When you trust your heart, things will flow more smoothly and naturally, which are both qualities of great conversations.

Downloadable and Printable List of Questions to Ask a Guy

Here is a downloadable and printable List of questions to a guy (right click the image and select Save Image As...) :

More Great Ways To Talk to Guys

Having specific guides can help with any challenges you might face.

So if you need more than just great questions to ask a guy,

We've got you covered:

  1. Ready to take the next big step? Here's how to ask a guy out.
  2. Want to show that you're interested in him? Check out how to flirt with a guy.
  3. Wondering how often you should be in contact? Our should I text him guide has all the answers!

In Conclusion

With all of these great questions to ask a guy, you'll never be at a loss for how to start a conversation with a guy, or how to keep that conversation fun, interesting, and engaging.

No matter what your reason for reading, we hope that you'll use this great information to get out there and start practicing!