56 Deep Questions to Ask a Guy to Build Attraction

deep questions to ask a guy

Ever wondered what deep questions to ask a guy to build attraction between the two of you?

Physical attraction is one thing, but how do you take things to the next level and build that all-important emotional connection?

Because it doesn’t just happen by magic.

Usually, one partner takes the lead in triggering emotional connection. And guess what? Women usually make the first move.

But how do you take a guy from that fun and flirty stage and smoothly transition into something deeper without it being obvious?

You ask him questions. But not just any questions.

These aren’t yes or no questions; they’re open-ended questions. Questions that will encourage him to open up and share personal things with you and talk about things he cares about.

These questions are designed to get him thinking, which will lead his attention back to you, and position you as a woman who understands him in a way that no one else does.

In 1997, psychologist Dr. Arthur Aron conducted a study called 36 questions to fall in love. Men and women who didn’t know each other were brought together and given a list of 36 personal questions to ask each other. At the end of the questions, they had to maintain eye contact for four minutes. Six months later, one of the couples got married!

So, asking the right questions can definitely help build attraction and a connection between two people, especially if your answers align with each other’s values and lifestyle choices.

Here are 56 deep questions to ask a guy and build that emotional connection.

1. What’s the last adventure you went on?

This is a fun way to get him to talk about places he’s traveled to and exciting experiences he’s had. What does adventure mean to him? What kind of places does he like to explore? Maybe you’ve both been somewhere that you loved.

2. What’s the one thing you are most passionate about?

Knowing someone’s job title will only tell you so much about them because many people haven’t yet figured out how to turn their passion into their work (or don’t want to).

This question will be a deep dive into his soul. What does he love more than anything else?

People light up when they talk about their passions.

3. What’s your greatest accomplishment so far?

Find out what he’s most proud of achieving in his life so far and why this matters to him so much. Celebrate his accomplishments with him, and show him there’s plenty of time to achieve bigger and better things.

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

This question will help you get a glimpse of what his day-to-day routine looks like. Is he up at the crack of dawn ready to face the day, or does he enjoy sleeping in and do his best work late at night? If you’re opposites, that’s not necessarily a bad thing.

5. What are your personal goals?

What does he want to achieve in his life? Is he currently working towards any of those goals, or are they in his future? Is he very goal orientated, or does he not have any goals?

6. If you were a superhero, what would your superpower be?

The superpower question is always a fun one to ask, and you can learn a lot from his answer. Is his superpower rooted purely in self-gain, or is it selfless and something that helps others?

7. How do you feel about your job/business?

You’ll find out if he loves his job or is solely in it for the money. If he doesn’t enjoy it, is he doing something to change that, or has he resigned to a life he doesn’t love?

And if he does love it, what does he love about it? And does it ever become all-consuming and encroach on his personal life?

8. What would you want to do if money wasn’t an issue?

This is up there with the best deep questions to ask a guy. Who doesn’t love talking about their fantasy life? You’ll find out the kind of life he dreams of living and why—a brilliant way to build an emotional bond.

9. When did you feel the happiest growing up?

When you ask a guy to tell you a story or memory from his childhood, it almost guarantees to elicit strong feelings within him. Chances are good that he’ll get really into it and share something profound with you that he hasn’t told many people.

10. If you could describe yourself with one word, which would it be?

It’s tough to ask anyone to summarise themselves in just one word, which is why this can be such a revealing question. Pay attention to whether he goes for a simple word or a complex one. How does he see himself, and do you think his word matches what you know about him so far?

11. What seemingly insignificant thing always makes your day better?

It’s the little things that matter most in life, but we often overlook them. We can focus on big dreams and goals too much and forget about all the small things that are already happening and make our lives beautiful.

This question will encourage him to practice gratitude and make him feel appreciative for what he already has—and he’ll remember that you made him feel this way.

12. What’s your zodiac sign? And do you think it describes you?

Horoscopes are fun to talk about because they’re pretty light-hearted but can reveal a lot about how we view ourselves and our world.

Bonus: if he asks, “do you mean my sun sign?” That means he’s into astrology and probably knows his whole birth chart. If you do too, this will be a lot of fun to share.

13. What’s your favorite book?

You’ll find out whether he enjoys reading much, and what kind of books he loves to read. Maybe he’s the kind of guy who always skips to the end to see how the story unfolds before committing to reading it. Maybe he never finishes books, which could extend to other things in his life. Or maybe he struggles with reading and is more of a movie guy.

14. What makes you a little bit embarrassed?

It’s great to find out what makes him secure before you’re confronted with it in a real-life situation. You’ll be prepared and know where it’s coming from and how to deal with it. This is why it’s another one of the great deep questions to ask a guy.

15. What is your most embarrassing memory?

Asking him to share his most embarrassing memory requires him to be totally vulnerable with you. Naturally, he might be hesitant or feel uncomfortable at first, depending on what he’s about to share. But if he does share his truth with you, this will build trust between the two of you and is a great step towards a deep attraction.

16. What’s a random hobby you’ve always wanted to try but never have?

Maybe you can try it together on your next date!

17. Has anything ever happened to you that you can’t explain?

This is one of the deeper questions to ask a guy on this list. It’s venturing into fate and destiny and a higher source that we cannot see or explain.

18. Are you a cat person or a dog person?

This question works on so many levels. It’s playful, and it really will tell you a lot about each other. Cats and dogs are very different animals, and most people love one and hate the other!

19. What do you expect from a loving relationship?

old couple kissing

Confused about deep questions to ask a guy? Ask him to share what he wants and needs from a romantic relationship. It’s good to know early on so you can see whether you’ll be able to offer that to him.

20. What are you most grateful for in your life?

Another beautiful question to get him in a zone of gratitude and appreciation for all that’s good in his world. Plus, you’ll get a glimpse of the things he values most.

21. What would your Shark Tank idea be?

Men’s Health asked many people what the best first date question was they’d ever received. One woman said someone asked her what her Shark Tank idea would be. She loved the question because it was unexpected and a great way to see into the inner workings of someone’s mind.

22. If you could live anywhere in the world, where would it be?

Is he more of a country-side, small-town kind of guy or an urban city lover? Would he love nothing more than living on a beach on a tropical island somewhere remote, or does he want to feel the hustle and bustle of the streets and nightlife around him?

This will tell you where his head is at for the future.

23. What’s a personal rule you have that you never break?

Who knows what he’ll share with you? This question leaves things wide open, and it gives you an insight into his morals.

24. What’s the one thing you’d most like me to know about you?

What does he specifically want you to know about him? His answer will likely show you what he believes to be important to you or your future relationship.

25. What is something you believe that most people don’t?

Maybe it’s God or ghosts or aliens. Maybe he’s super into conspiracy theories. Or maybe he believes in reincarnation.

26. If you were writing a book about your life, what would the title be?

Who knows, maybe he is actually writing a book, or maybe he has already published a book! Or maybe you have.

27. Tell me what your perfect day looks like

This is one of those deep questions to ask a guy that will show you the kind of life he wants to live and what’s important to him.

Is he a simple kind of guy who loves a hot cup of coffee in the morning while he reads the paper? Does he enjoy a daily walk by the beach and enjoy nothing more than spending time with his loved ones? Or does he want to spend most of the day working and building his empire?

28. Favorite food of all time?

Another super fun question to ask, because who doesn’t love talking about food!

If he’s relatively healthy and conscious about his body and appearance, you’ll probably get a healthy answer. Or maybe he’ll share his guilty pleasure with you that he saves for special occasions.

If you get a fancy answer, chances are he enjoys cooking, in which case you can tell him you would love him to cook for you!

29. What’s the most romantic thing you’ve ever done for a woman?

deep questions to ask a guy

Romance isn’t everything, and I always believe it’s best to focus on partnership. But I know that women love to be woo-ed. So, let him share with you his best moves. If he tops them with you, you know he likes you.

30. What is your best friend like?

His best friend might be a guy or a woman, his brother or sister, or even his mum or dad. This is a beautiful way to get him to open up about someone he loves and what friendship means to him.

31. What’s the biggest life lesson you have learned?

This question is likely to get him to share a story with you when he learned this lesson and why it has shaped his life in such a big way.

32. What’s something you’re bad at?

Opening up about what you suck at requires you to let your guard down. Plus, it’s funny!

Are you both terrible cooks who end up burning pasta?

Are you someone who struggles to receive compliments and will always deflect them?

Has he had a gym pass for the past year and been in once?

Is he able to laugh at himself when he shares this with you? Is he able to let you in?

33. What’s the most significant love lesson you have learned?

Has he learned anything from his past relationships? Has he had a serious relationship at all? And how has this changed how he approaches relationships today?

34. Who has had the most significant impact on your life?

His answer to this question will tell you a lot about a person who likely means a lot to him, someone he respects and admires greatly.

35. What is something you have never told anyone else?

We all have secrets, and this question will require him to be vulnerable and open up with you. It’s a great way to build trust and a strong bond between the two of you, which is precisely what you want.

36. Was there ever a time I crossed the line or hurt you?

couple in love

This isn’t a question for too early on in your relationship. But once you’ve spent enough time together and have deepened your connection, this question is a great way to trigger an emotional response.

It gives him a chance to share his side of something and talk about his feelings. Plus, it gives you a chance to apologize for hurting him.

37. Would you say you’re an introvert or an extrovert?

Depending on how long you’ve been seeing this guy, you might have a good idea of which one he is. But the character he projects might be different from his real character at heart.

38. What do you find attractive in a woman?

Everyone finds different things attractive in a potential partner that go beyond the physical. This is one of the more fun, light-hearted questions to ask a guy but will still help you understand what he values most in a woman.

Does he describe you? Or does he describe someone radically different from you?

39. What’s the most spontaneous thing you’ve ever done?

Is he a spontaneous person, or does he live his life in more of an organized and planned way? Has he ever done something unexpected? Or does he struggle to let go and live outside of the box?

40. If you could go back and tell yourself one thing, what would it be?

This is one of the deep questions to ask a guy to get him to open up about his regrets. Does he have any? What did it take him longer to learn than he would have liked? And how would he have lived his life differently back then, knowing what he knows now?

We’ve all made mistakes in the past, but this will tell you how he feels about his.

41. Are women equal to men?

deep questions to ask a guy

Such an important (and serious) question to ask a guy. You don’t want to end up in a relationship with a guy only to find out that he expects you to stay at home and cook and clean while he goes out to work. Or to have to listen to him making sexist and chauvinist comments.

If he’s a secure new age guy, he’ll believe in gender equality. Don’t waste your time with anyone who doesn’t.

42. What are your pet peeves?

This is one of the deep questions to ask a guy to help you and him on multiple levels. You’ll find out what bugs him the most, and then you can reflect on that and see if you have any of those habits. If you do, and you know you’re not likely to change anytime soon, be open about it.

43. When was the last time you cried, and why did you?

Men are taught from a young age that to be a “man” means to be strong and “masculine” at ALL times. Crying is definitely not seen as manly, and therefore must be avoided at all costs. Unfortunately, most men are still wired this way. So when we do cry, it’s usually a pretty big deal.

44. What is something you are really good at?

Everyone loves a chance to brag a little about themselves and remind themselves of what they’re great at. This question will give your guy a chance to do just that. Plus, you’re showing him you want to know more about who he is.

45. Do you believe in a higher power?

Is he religious, more of a spiritual kind of guy, or an atheist? What led him to his current views, and how strongly do they influence his life? And how do your own beliefs align with his?

46. How do you express your feelings for someone?

Asking this question will help you learn more about how he interacts with women he likes. This will give you a big clue as to where you currently stand with him!

47. What’s the best thing about being in a relationship?

You’ll find out what he values most about being in a relationship, plus what he has learned over the years from his past relationships. It might be something simple like cozy nights in or being best friends with someone you’re also in love with.

48. What’s your biggest fear?

We all have our fears, and most of them tend to be irrational. Are his irrational, or are they the result of a bad experience in the past? You might get a generic answer like spiders or heights or something a little deeper.

49. Where is the craziest place you have ever had sex?

Men usually like it when women talk openly about sex, and this is a great question to show them that you’re comfortable with it. Plus, the conversation can get pretty sexy. This is one of the more playful, deep questions to ask a guy and can help lighten the mood if the conversation gets too heavy.

50. What do you expect from your partner?

What does this man need and want from you in a relationship? Is it loyalty, respect, support, or something else? What are the things that are most important to him? A really important question to ask any guy you date.

51. Have you been in love before?

The older the guy is, the higher the chances he has been in love. Although he may have thought he was in love, then realized afterward that it wasn’t quite the full package.

52. Have you ever gotten your heart broken?

Again, the older he is, the chances are he has had his heartbroken—at least once. This gives him another opportunity to let his guard down and open up to you about being hurt.

53. Are you still friends with your exes?

An important question to ask because if he is still friends with his exes, that means you’re probably going to have to see him with them at some point if you continue dating. Are you okay with that? Would you get too jealous or suspicious?

54. Do you want to get married someday?

married couple photo

If marriage is important to you or something you definitely don’t want to do, you must see where his head is at. Does he see marriage in his future? Are you both on the same page?

55. Do you want children?

It’s hard to believe, but some couples never end up having this talk. Finally, one day one partner will say that they want children, and they’ll be shocked and devastated by the news that their partner doesn’t want to be a parent. Avoid this from happening and get this question out there sooner rather than later.

56. What is your favorite memory with me?

This is a fun question to ask because it gets him thinking about you and what he likes about you. Get him to describe his memory in as much detail as possible for maximum emotional impact!

Conclusion: There are so many deep questions to ask a guy to build attraction!

If you’re ready to start building on your physical attraction and take things to the next level, these questions are guaranteed to do just that. And if you’re looking for some extra help, we’ve got you covered.

I’d love to know if you’ve ever asked a date any of these questions and what happened? Did it help build an emotional connection between the two of you?

Let me know in the comment below, ladies.

deep questions to ask a guy

Also, if you’d like to join me on a brand new webinar to learn “why men flake, avoid commitment and consistently ghost until they meet a woman who’s following these 7 simple steps”, then register here (it’s 100% free).

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Adam LoDolce

Love Strategist

My true passion in life is transforming your love life by giving you specific tools and techniques that you can use to attract long lasting love. I got started when...Read Adam's Story

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