50 Deep Questions To Ask Someone To Know Them Better

How well do you know that boy or girl? Especially those ones very close and dear to you. You probably know everything there is to know, but it would surprise you that there are things you still do not know or things you assumed about them which are not true.

To help you get closer to knowing more about whom they are beyond what you already know, we’ve compiled 50 great questions you can ask your friends. Most of these questions are personal, deep, and searching.

Deep Questions To Ask A Girl

When you have gotten comfortable around a girl, you can ask her any of these questions to find out something/s you never knew about her. These questions will reveal things about her to you personally; her answer/s can be hilarious for some, shocking to others, and even emotional for most. In all, you will end up knowing her a lot better than you thought you knew her.

  1. Who was your high school crush?

This question might catch her off guard if you both have never talked about your past crushes/relationships before. It should bring pleasant girly memories to her, and if you are observant enough, you can pick out a few things to playfully tease her about.

2. Who is your most embarrassing secret current crush?

Okay, so it’s the present. This might not be embarrassing to you but to her, admitting who her crush is might throw her off balance. No matter her response and how she feels about it, egg her on if you think she deserves the crush, and the crush deserves her too.

3. How many times have you made out with someone while drunk?

When people are drunk, science says a neurological and psychological regression goes on in their bodies. The higher the blood alcohol level of the body, the more one tends to let out one’s feeling, one of which is a drunk kiss which can culminate in making out.

4. How do you see me?

Look her in the eyes when asking this question and maintain the gaze as she answers or attempts to answer. If she has a crush on you, she might seem shy and fumble in her response. If she likes you as a friend, she shouldn’t feel shy for any reason but should confidently look you in the face and answer.

5. Would you relocate for love?

A survey conducted by Home.com reported that of the 5000 study sample, 1 out of 5 has relocated to be with their partner at one point or the other, and 70% of these “love moves” have been hugely successful.

6. What is the longest time you’ve ever gone without shaving your legs?

There is no rule on the intervals ladies should shave their legs; while some shave in a matter of days interval, others do theirs in weeks. It all depends on what works best for someone, and her answer to this question is what works best for her.

7. What’s surprising about you?

This is still a surprise till after the very moment she tells you. It might be a secrete she has hardly ever let someone in on or perhaps something that no one has noticed about her. No matter the answer, it seizes being a surprise the moment she tells you.

8. What or who would you sacrifice your life for?

It all depends on what or who she values most and holds dear, and this is something she wouldn’t tolerate anyone to mess with. It would be best if you accorded that person thing as much respect he/she has for it.

9. What was your first date like?

First dates are often memorable either for some excellent reasons or perhaps for some hard to forget embarrassing occurrence. No matter what her story is, remind her about the future, especially if you plan to ask her out on a date.

10. How do you feel about infidelity/cheating in relationships?

No one tolerates cheating even though both sexes cheat for various reasons. The effects of cheating are even more devastating to women as research has shown that it causes psychological damage to their health, feeling of rage, loss of sex drive, and damage to self-image.

11. What would you do for the person you love?

Some of the things girls do when they are in love include discussing her plans with you, asking for your advice or opinion on matters bothering her, be affectionate towards you, respect and encourage, sincerely compliment, believe and share in your interest, etc.

12. How Do You Know When You’re In Love?

When a girl is in love, she will often spend more time with her love interest, share her secrets, and even express her love for him. Of course, she will cut off others or reasonably reduce her association with other guys. After all, guys are naturally jealous lovers.

13. What ice-cream flavor is absolutely disgusting? 

Just don’t stop at finding out which ice cream flavor she doesn’t like; go further and find out her reason. Perhaps it has to do with a bad experience she had with it, which has stuck.

14. What questions would you ask if you were in a dating game show?

It can be a series of general knowledge, background, situational, unique first date questions, or even the romantic flirty questions, which hardly ever come last. I would expect her to ask you this question the moment you are done answering.

15. Are you easily offended?

It can also the rephrased as, are you hot-tempered? If she responds in the affirmative, don’t be too hard on her, as she can work to improve.

Deep Questions To Ask A Guy

Between boys and girls, researchers opine that girls are more emotionally expressive than boys, and this has been the societal norm for a very long time. Be that as it may, it does not mean that most guys will keep mum when you ask them deeply personal questions. While some might be cautious about their response, others might let it all out and even become emotional in the process. Below are questions to help you find out which part your guy is on.

16. What do you think about men cooking?

Gone are the days when it is said that the kitchen is a woman’s world. These days, it’s a man’s world too, and even more so, many men are eking out a living working in kitchens.

17. What do you cook or bake the best?

Don’t just as to know, dare him by asking him to cook or bake the meal for you then you can truly judge how good or so good the cooking/baking is. Compliment him afterward. Guys like it when they show off their cooking skills and get applause for it.

17. What was the name of the first person you ever had a crush on? Why did you like them?

Most guys often start having crushes as teens at the time puberty sets in. But for some, this might come when they are way quite young before puberty.

18. What’s the weirdest thing that turns you On?

It might be something he has a fetish for, which ordinarily might be bizarre to you. You probably wouldn’t have known this if you didn’t ask. What’s yours?

19. What’s your most embarrassing sex story?

It might be embarrassing yet hilarious at the same same time. So for either or both reasons, he has kept it to himself all this while.

20. What makes you feel super loved?

Just like girls, guys need love and affection even though they tend to hide this and act all manly most of the time. But deep in their mind, they crave that tender-loving hug, kissing, and showing of affection from their partner.

21. Are you more into looks or brains?

Different strokes for different folks. It is brains over beauty to some guys, while to others, it is beauty over brains. No matter the answer he gives you, don’t stop there. Try and find out why he has a preference for one over the other.

22. What did your past relationship teach you?

It could make or mar his perception of relationships depending on all that transpired in the relationship and his perception of them.

23. When was the last time you slept outdoors?

It could be after an all-night party or perhaps something less adventurous like losing his keys. Ask him this question like you are investigating him and also find out his reason. Was it worth it?

24. What task would you really fail at doing?

Most guys wouldn’t admit that they aren’t good at doing something. If he does admit, he has likely tried doing it many times without much success. Just see if there is a way you can help him succeed at it; he will be grateful.

25. When was the last time you cried, and what made you cry?

It is given that girls cry more often than boys do, but when boys do cry, they are at their weakest and sometimes helpless.

26. Are relationships meant to last forever?

Relationships that are mutually beneficial to both partners will last a very long time. But one which thrives on the expense of one of the partners will end not too long after it started.

27. What are you most passionate about?

It could be his job or his hubby or a career he intends to pursue. Encourage him in it if he’s already doing well thereof or offer some advice and/or encouragement in areas where he needs it.

28. What is the greatest struggle you’ve overcome?

Life happens to us in various ways, and we all face different struggles as we journey through life. This question might make him remember some of the things he failed at or even his biggest triumphs so far.

29. Are you religious or spiritual?

Is there really a difference between being religious and being spiritual? Yes, there is. Being religious means having a firm belief in a set of organized beliefs and practices associated with a particular religion, while being spiritual means having a fulfilled sense of peace and purpose.

30. What’s your philosophy in life?

One’s life philosophy is a set of guiding principles that the person lives by. It cuts across things as little as what you say, how you act, and how you relate with other people.

Deep Questions To Ask Anyone To Know Them On A Deeper Level

More often than not, it is not enough to know just the basics about someone, especially when you are genuinely interested in the person. Finding out some deep and personal things about the person can redefine how you see him or her, give you a better perspective on who they truly are and perhaps, improve your relationship with such a person. The questions below are perfectly apt to get you through.

31. What is the one thing you regret having done or not done in your life?

When he/she has answered this question, find out why he/she regrets it if it is not obvious already. Mind you; this might be the person’s secrete, so be sure to keep it as such unless he/she says otherwise.

32. What do you think about me?

You never can tell how someone sees you or interpret your actions till you ask them. If the response you got shocked you, you can clarify things to them to understand you better.

33. What do you often like talking about?

It could be about sports, politics, tech, medicine, food, travels or even films and books. Generally, people like talking about things they are passionate about.

34. Which parent has the most influence on you?

It’s a truism that mothers are the most dominant parent in the family, and even recent statistics have shown that 53% of Americans admit that their mother has the most influence on them.

35. Which of your parents do you like most?

This question calls for deep reflection because even though mothers are the most dominant parent in the family, they are not necessarily the most loved. Some people still have a preference for their less domineering fathers.

36. Is there something you wish you had said sorry for but never did?

Admitting one’s wrongdoing and apologizing is quite hard for some people to do, and more often than not, they end up regretting their actions afterward. Even so, admitting that they felt bad for not apologizing may even be more difficult.

37. Are you proud of what you’re doing with your heart and time right now?

Sometimes people find themselves doing something they aren’t happy doing, but they keep on doing it for some reason or the other. If it happens to be the person’s job, by all means, comfort him/her and suggest the possibilities of moving on to something better in the future.

38. Has anything/anyone ever saved your life before?

If someone has ever saved your life before, you will understand better what that feeling of gratitude is like. This question might get him/her emotional depending on the circumstances that surround the event.

39. Would you ever adopt a child?

More people opt for adoption these days than deciding to have their own child, unlike what it used to be in the past. So don’t just leave the question on a yes/no answer. Try and find out the reason/s behind his decision.

40. What’s your weirdest habit?

Some of the weirdest habits people have been reported to have include having conversations with themselves, measuring time with music, smelling books, eating nails, covering mirrors before going to bed, etc.

41. What was the best phase in your life?

There are 7 phases of human life: infancy, early childhood, middle childhood, adolescence, early adulthood, middle adulthood, and old age. Typically, most people tend to have the best phase of their life in their early adulthood, but there can still be exceptions.

41. What was the worst phase in your life?

This will most likely be that phase in someone’s life when he/she was at the lowest. No one likes sad memories, so you should move on from this question pretty fast unless otherwise.

43.  Is what you’re doing now what you always wanted to do growing up?

Childhood dreams, in reality, aren’t always what they were imagined to be, and even though some people end up pursuing other life interests than they imagined growing up, most still don’t regret their career path, as this survey stated.

44. Does the study of philosophy ever lead to answers or simply more questions?

Philosophy isn’t ordinarily about finding and giving answers to everything with a question, but it’s more about questioning everything and forming perspectives on them rather than answers.

45. How often do you lie?

Are there people who are completely honest in all they do; void of lies? It might be hard to find, even though this is not impossible. An average person reportedly lies about 1.65 times a day.

46. What’s the worst lie you’ve ever told?

Things people typically lie about include relationships, finances, job/profession, age, sexual partners, ethnic background, etc.

47. What inspires you the most?

It could be a challenge that fires the person up to be at his best or the need to keep to a promise made to a loved one.

48. What Do You Take For Granted?

People often take for granted what they don’t attach much importance to. But if his/her response is a reason for concern, you should probably stretch the conversation to find out why and advise better.

49. Are you living a meaningful life?

This question can’t be any blunt than it is already. The person you asked this question must have reflected on it personally and already has an answer at one point or the other. But if not, and no matter, you too can reflect over his/her life dreams and where the person is at.

50. Would you rather live a long and boring life or a short but unfilled life?

Everyone chooses to do with their lives what they think is best for them.


No matter how you thought you knew someone, there is still something new you can find out about them whenever you ask some thought-provoking questions. The questions above cut across all facets of life like personal philosophy, family life, belief system, career, relationship, etc. With every one of them, you will gain more insight into whom that boy or girl truly is.

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