50 Interesting Questions to Ask a Guy

By on November 18, 2015

There was a study done that proved you can fall in love simply by getting intimate with someone and looking them in the eye. And by intimate I mean by asking questions; revealing things we don’t always reveal when first meeting someone.

When you first start dating someone, you no doubt want to build up that feeling of intimacy and enjoy it as the butterflies start flying around in your belly and theirs. You also want to keep the intimacy building once you’ve gotten to know someone – don’t get lazy. Always strive to find out what’s going on in their heart and soul.

Lastly, sometimes you need to get a conversation going with a date and asking questions lead to that. Don’t over do it – it’s not an interrogation. Just simply ask questions that lead to new topics to talk about. Remember to tease, flirt and challenge them a bit as well!


1. What’s a really good day you’ve had lately?

This is a great question to find out what makes him happy on a day-to-day basis. It also opens up to discussions about what your day-to-day lives look like, what you like about it and what you’d want to change.

2. Name three things you’re the most grateful for right now.

What makes someone grateful is often what makes someone happy, which is helpful to know when dating someone. Gratefulness also tells you a lot about a person’s ability to appreciate life. Some appreciate the smallest of things, some won’t be happy until they’re a millionaire.

3. If you could change one or two things about your life right now, what would it be?


Understanding someone’s problems, or challenges, at the time helps you understand where they are at in life and if you are at the same place. It can also help you understand what they perceive as a problem. Some people easily overcome obstacles, others get stuck.

4. If you could go back in time to relive one moment/day of your life, what would it be?

This is an excellent way to find out what someone appreciates in life so you understand if you enjoy the same things. It’s also intriguing – you get to know a little bit about your date’s past; what shaped them.

5. If you could go into a magic machine right now and it would take you to anywhere in the world in a couple of seconds, where would you go?

Hopefully he will tell you he will take you to some romantic spot on the Earth, but if it happens to be to go on a tour of NASA, at least you know that’s what tickles his fancy…

6. If you could take me anywhere, where would it be?

If he didn’t catch on with question number five, then this might be the cue he needs to tell you about a place he’d take you to. Depending on where you are at in your relationship the answer might greatly vary – in the beginning when dating someone he might be happy just to take them to a fancy restaurant. If this is several months into dating a guy he might prefer to take you on some mind blowing romantic date in Paris, or show you a place that truly matters to him.

7. What are the accomplishments you are the most proud of in your life?

Will definitively reveal where his priorities are at – some are happy to have made a million dollars, others are happy to have donated a million dollars.

8. If you could do one thing for the world, what would it be?

This will probably answer whether he would prioritize going green, world peace, or getting rid of hunger. Whilst each is a note cause, you will find out what fires him up; what he’s truly passionate about.

9. What cause would you like to contribute to, or are you already contributing to?

This shows what he cares about in life, as well as, hopefully, his generous and kind side.

10. If you could do anything for a day, what would it be?

Would he raise money for a charity, for his own business, travel to some exotic destination, eliminate poverty, or take a trip to the moon? Again, it will tell you a lot about his personality.

11. Where do you see yourself five years from now?

This is the classic job interview question, but it will tell you where he’s heading in life. Especially helpful if you’re looking to settle down with someone, or find out if they want to go to college!

12. Where do you see yourself ten years from now?

A bit further perspective of what he wants to achieve in life. Will also tell you what’s really important to him and if he has goals he’s willing to fight for.

13. What’s your favorite drink?

Always helpful to know! Plus, if you both happen to be into food and drink, this can lead to interesting conversations about recipes, bars, etc.

14. What are your favorite kinds of foods?

This is like question 13, only referring to food instead. Great to know if you plan to invite him over for a meal, or take him out to a restaurant.

15. If you were showing a tourist around your town and wanted to give them an extraordinary experiences, which places would you take them to?

Will tell you what his favorite spots in town are! Good to know if you are planning a date. Will also tell you what he appreciates in life.

16. Do believe in anything supernatural?

Now this may get you into a discussion about both Gods and ghosts.

17. Do you believe in karma?

Again, this goes into a spiritual realm. Most people find if they date someone they want to have fairly similar spiritual values.

18. If you wrote a book (or had someone write it for you), what would it be about?

Shows you what they think it would be important for the world to know…or be entertained by (presumably what entertains them).

19. If you were a superhero, what powers would you have?

Would they be able to create food out of thin air, or stop criminals with some wicked talent?

20. What’s a pet peeve of yours?

This one often makes you laugh – we all have some habit or other that’s a little bit wacko.


21. If you were President for a day, what would you change?

Now here’s their chance to impress you with how amazingly well they’d run the country! And what they find important for a good country for that matter.

22. What’s the one dish you absolutely rock cooking?

What’s their signature dish? The one they’ll cook you to impress?

23. Have you ever had such a vivid dream you still remember it to this day?

A look into his subconscious…

24. Do you believe in personal development?

Are they always working to improve themselves, learn and grow, or are they pretty happy with their habits and don’t care to expand their mind?

25. What’s the most romantic thing you ever heard of?

Will definitively tell you more about what they consider romantic!

26. What’s one love quote you’ve heard that struck you as true?

Will give you a nice insight into how they view love. And, potentially, what would make them happy in a relationship.

27. What’s one thing you always think of when people say “I couldn’t live without this”?

This will tell you about one of his favorite things in life, be it baseball or his mom’s cookies.

28. Who are some people you truly admire?

What people admire in others is often what they strive to achieve for themselves.

29. Who would you invite to a dinner party if you could invite anyone, dead or alive?

This will likely tell you a lot about the guy’s interests, passions, ideals and dreams.

30. What would be your ideal date night?

Listen close – you may one day have to plan this date…

31. Do you believe in marriage?

Not necessarily a question for a first date, but definitively something you can ask when discussing relationships and how you view them.

32. What would you say are three ingredients for a good relationship with a woman?

This will tell you a lot about what kind of relationship he envisions for himself. Though remember – what he dreams of is not necessarily what he will give.

33. What would you say are three ingredients for a good relationship with a friend?

Is he a man who believes in honesty and kindness, or support and loyalty?

34. What are things someone can do to make you feel good?

Does he get happy when someone cooks for him, or holds his hand?

35. What do you think is the reason why some people are still happily married when they’re 93?

Again, this refers back to the things he believes constitute a great relationship. It will likely also show you how experienced he is in that field. If he doesn’t have much experience, he might think love without action goes a long way.

36. What do you find really attractive in a woman?

Now, you don’t want to go and become someone you are not – he already finds you attractive or he wouldn’t be on a date with you. However, if he’s someone who just can’t resist a short skirt, or a long hug, you might want to supply those at some point just to bring a smile to his face!

37. Is there any one place on Earth you’d love to go to and visit, or live in?

Does he dream of exploring the white sands of foreign beaches, archeological digs, spiritual temples, or the bar scene in an exotic city?

38. What’s the sexiest thing a woman can do?

Now we’re getting into the hot topics…

39. Do you believe in love at first sight?

Most people confuse love at first sight with a great relationship at first sight…but let’s not talk about my opinions on this, you’re sure to want to know his!

40. What’s one thing that’s kept you awake at night?

Is it the invention he’s working on? Or the bad thing he did? Or maybe the thought of you?

41. Do you have any one dream you feel you truly need to achieve?

Great to know if you have dreams that complement each other. And if you admire him for his dreams. If you intend to date him in the long run it’s really important you believe in him and admire what he is looking to achieve in the world.

42. Would you rather take trip to the bottom of the sea or to space?

Simply an interesting question.

43. What’s one of your favorite memories from childhood?

What are the things that influenced him positively growing up?


44. What’s one of your worst memories form childhood?

What are the events that shaped him negatively, or ignited him to become a better person as he learnt from the hardship?

45. Who is one person yo trust absolutely and why?

What makes him trust someone?

46. What should one do to make you feel good?

Does he feel good from hugs and caresses, or kind words?

47. What do you think is one of the most important things to learn in life?

Will give you a clue to what he values in life.

48. What is one thing that’s inspired you to become a better person?

Always intriguing to find out what inspires someone.

49. Name one book, movie or TV show that changed your life.

Again, it will clue you into his personality and the things in life that have shaped him.

50. Don’t tell me what they are, but do you have any secrets that you really don’t want the world to know?

Is he secretive? Or does he have something to hide?

If you want to find out more about the experiment that revealed that strangers can build feelings for each other rapidly by asking each other intimate questions, you can check it out here. And remember – questions aren’t just for first dates. To keep a relationship alive you have to keep exploring one another, both by asking questions and by doing new things together, so that you grow together. Stagnation is the death of most relationships, so focus on keeping things alive and interesting. Routines are great, if they are good ones, as is doing something unexpected.

One thing to bring with you as well is this – we all change from day to day. Explore the person you love every day. Look them in the eye to find out how they are feeling and who they are today. There’s nothing more romantic than someone looking you in the eye, searching your soul.

1507760_10152392614860079_8379465670289960282_n copy 2By Maria Montgomery – Maria is a freelance writer, director and social entrepreneur. She’s also the spokesperson for The Little Angels Community Center and an avid blogger. You can find her somewhere between Cape Town, London and L.A., where you will most likely find her in the hills, looking out over the city she loves. @OhMyMontgomery

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