Deep Questions To Ask A Guy (To Reach His Heart)

Deep Questions To Ask A Guy (To Reach His Heart)

Knowing deep questions to ask a guy can be what makes your relationship go to the next level and ultimately succeed.

Deep Questions To Ask A Guy Are Not “Fun”

Warning: these questions are not meant to be fun or to be lighthearted. These are mostly serious or heavy topics that are meant to strike up a conversation that gets past the surface level information, far beyond the superficial and into the heart of who the person is.

These questions are designed to get you guys to know each other in a more profound, personal and genuine way. The way this works is you will ask these questions but also share your own answers to highly personal questions as the conversation goes on.

These are the types of questions you ask when you feel your needing a little extra from the conversation and want to get past the basics.

MORE: 50 Great Questions To Ask A Guy

Knowing A Person Beyond The Mask They Wear To Society Creates True Love

Deep questions are the mechanism by which you will get to know him for the person he is, the man behind the mask he wears to society.

Take The Quiz: Is He Losing Interest?

What makes a difference between a guy thinking you are his soulmate versus him losing interest is whether you truly know and understand who he is. If you don’t know a guy on a deep level, he will lose interest.

Click here to take our quick (and shockingly accurate) “Is He Losing Interest” Quiz right now and find out if he’s really losing interest in you…

The knowledge of who your partner truly is really is the key to any real relationship. When you fall in love, or out of love for that matter, it’s generally because you have reached the core of that person and have a perfect portrait of exactly who they are on the inside.

Some nice guys can be extremely rude and vindictive in reality, while on the opposite end, some guys who come off as hot tempered and mean are actually some of the kindest souls.

Deep Communication Is Key

In order to find out who someone truly is, obviously there has to be communication, but it must be deep communication; meaningful questions that are asked and answered.

If I’m planning on marrying or breaking up with a girl, it’s not because of her favorite color! It’s because of how I know her from the inside out.

But how do we really get to know someone?

If you’re in a relationship and haven’t really gotten to the “good stuff” yet in your conversations, these questions will be great starters to get things a little more serious, and most importantly, will give you much better insight into the psyche of your partner.

MORE: 110 Questions to Ask your Boyfriend

Being A Good Listener Is As Important As Questions You Ask

Deep questions will lead to deep answers, which should solidify your relationship in a positive way. Just always remember to listen and to gauge the reaction of your partner. Be very attentive to how you think they are feeling or reciprocating!

Being Slightly Uncomfortable Is Normal

Some stuff is just plain uncomfortable to talk about, but that is the point of these questions! Everyone has an external version of themselves that they present to the world. It is about getting to the internal side of that person.

Obviously if someone doesn’t want to go into something traumatic, don’t push it. Some people will simply just clam up about a topic, and nothing will change that.

Acknowledgment Is The Secret To Him Opening Up

I suggest that if there is something deep about a guy you really want to know and he’s not reciprocating, explain and acknowledge that you know how uncomfortable it must be and apologize- maybe even give a personal anecdote to break the tension and make him feel safe.

With true care and interest and taking small steps you can finally crack that guarded shell and tough exterior. Obviously, some people are much more secure with sharing personal information than others, so take it slow if you need to, and tread softly.

Surprisingly enough, from my own experience, when I get asked something I’m really not too keen on answering, I’ll get awkward and definitely a little edgy, but the second I see a kind face, and a look of zero judgment from my response, it is like a weight being lifted off my chest.

Its amazingly refreshing to have someone you can be totally honest and candid with, and it’s imperative to have that type of trust if you want to have a working relationship.

Being a great listener is a must. You must show you care and are actually interested in what they’re saying. We only want to open ourselves up when we feel the other person is really taking notes on what we’re saying and giving genuine, well thought out responses to what’s being told.

Remember… the questions are not meant to scare someone away, they are meant to discover who that person really is, and if you guys naturally fit together like peas in a pod.

MORE: 40 Personal Questions to Ask A Guy

Being judgmental is the worst possible thing you can be when asking deep personal questions, so even if some answers surprise you, stay cool! Realize you now know something that you can take a mental note of, and put inside your mental rolodex of that person’s attributes… and start to build a real “profile” of that person and who they are.

Remember, as I’ve stated before, we are all humans! We all make mistakes, have insecurities, and different beliefs. No one is perfect!

These are some great deep topics with questions that relate to each of them that will inevitable bring you to a much closer, deeper connection!

Existential Deep Questions To Ask A Guy:

Do you believe aliens exist?

Is there a god in your mind?

Do you believe in any sort of religion?

Why or why not?

How do you measure your life’s value?

What is the human race’s biggest screw up?

Is one life enough to complete all of our goals, and live out all of dreams?

Are people truly all equal?

Do you think certain people deserve pain and punishment?

What’s one thing we all take for granted?

Can people truly change themselves?

Why are some people kind, while others are mean and vindictive… maybe even evil?

Does humanity need to be saved?

Meaning of Life

Do we really have control over our lives?

Is it fate or destiny that controls us?

Is life fair?

Thomas Jefferson once said “the art of life is the art of avoiding pain”- do you agree with him?

Does everyone have a unique purpose on this earth?

We all feel we are “meant” to do something, that we are “here for a reason” and have purpose… is this true, or is it an inherent genetic delusion to keep us motivated and positive?

Does it disturb you that one day in the future, after you die, someone will be the last person to ever think about you?

With the knowledge of the size of the universe that we can prove, and a population of almost 8 billion, how valuable is human life on an empirical scale?

MORE: How To Never Run Out of Things To Say On a Date

Deep Questions To Ask A Guy About Death:

Do you believe in any sort of life after death?

Do you believe people will be punished for their sins?

Do you think we will be rewarded for our charity?

How long do you think you’ll be remembered?

Who do you think would show up at your funeral?

What would you have inscribed on your tombstone?

Who would receive benefits from your will?

What will people say about you in your obituary?

Have you ever had a close experience with death?

Have you ever had some close to you die?

Are you afraid of death?

Who would you feel justified in killing?

Would you die for a cause?

Deep Questions To Ask A Guy About The Future of Our Planet:

Is technology ruining us or saving us?

Do you think there is a possibility of a apocalypse, or some sort of dystopia that will happen in the near future?

Do you believe Thomas Malthus was correct and that overpopulation will eat the world’s resources dry and be our ultimate demise?

Do you think humans will ever have to permanently leave earth?

Is the world depicted in George Orwell’s “1984” a possibility?

What kind of technology do you think will exist a thousand years from now?

What will be the next mode of popular transportation?

Do you think countries will remain separate or will one day a new “one world” order exist?

Do you think technology will be able to keep up with the problems of humanity; Ie. such as depleting oil resources?

Do you think at some point we will all be one race?

When do you think we will find extraterrestrial life, if we do, and how do you think that will impact humanity?

Will we ever come to a true conclusion of why we are here?

Will we ever have every answer in the universe?

Will we have the technology one day to live forever?

Do you think virtual reality will ever be able to mimic reality so perfectly that we could not tell the difference?

Is something like “The Matrix” a possibility?

Will we find cures for all diseases?

“Personal” Deep Questions To Ask A Guy:

What’s your best childhood memory?

What is the most important event that ever happened in your life?

Biggest fear?

Biggest regret?

Happiest you have ever felt?

Saddest you have ever felt?

Most alone you have ever felt?

Biggest fear that you conquered or had to overcome?

Have you ever felt hopeless or like you want to give up in life?

Have you ever been in serious trouble with the law?

Have you ever struggled with substance abuse?

What’s the most embarrassing experience of your life?

Do you have any prejudices for certain things or people?

Do you hate anything?

Do you have any obsessions?

What was your first sexual experience?

Do you have any phobias?

So, there you go! These are some fantastic, really hard-hitting questions that will definitely move you forward from small talk to real self-disclosure and discussing genuine emotions. Just remember as I’ve said before, these are very serious questions that can be a little difficult to ask or answer.

Deep questions are absolutely imperative to have a true understanding of one another and can absolutely strengthen your love and connection with your significant other.

They may be awkward, but I feel there are more than necessary.

Take it easy, and let the questions and conversations flow naturally, and be sure to pay attention and make it a totally comfortable, safe situation.

The safe space you create will be good but what if he still emotionally withdraws, shuts down and pulls away?

Well, there are 2 big turning points every woman experiences in her relationships with men and they determine if you end up in a happy relationship or if it all ends in heartbreak.

So pay attention because the next step to take is vitally important. At some point he’s going to ask himself if you are the woman he wants to commit himself to for the long term…

Do you know how men determine if a woman is girlfriend material (the type of woman he commits himself to) or if he sees you as just a fling? If not, you need to read this next: The #1 Thing Men Desire In A Woman…

And the second big problem many women face: Do you feel he might be losing interest, going cold emotionally or pulling away? If so, then you need to read this right now or risk losing him forever: If He’s Pulling Away, Do This…

More reading:

20 Questions to Ask a Guy You Like to Get Closer

225+ Amazing Questions to Ask a Guy: The Ultimate List

40 Personal Questions to Ask a Guy

36 Deep Questions to Ask Your Significant Other

Want to find out if he’s really losing interest? Click here to take our quick (and shockingly accurate) “Is He Losing Interest” Quiz right now and find out if he’s really losing interest in you…

Take The Quiz: Is He Losing Interest?

30 comments… add one
  • china May 17, 2018, 5:12 pm

    the key to any real relationship to last is knowing who your partner really is. these deep questions can help if you want your relationship with your man to succeed.

  • emilia May 16, 2018, 6:29 pm

    i am looking forward to asking my boyfriend these questions and i am sure i will still discover a ton about him. these questions can really bond us for life.

  • ava May 15, 2018, 9:31 pm

    i always find myself on the hunt to find the things my husband and i have in common and these deep questions will help me a lot.

  • jessica May 14, 2018, 7:56 pm

    asking your guy deep questions is a good way to understand him better and also spend some time with him in a pleasant way. this is the only list i need to learn my man’s views.

  • chrissy May 10, 2018, 7:25 pm

    these are amazing questions that will make my man fall in love with me even more. asking him these deep questions will help me uncover his mind and can also bring up a discussion to make our relationship grow stronger.

  • diphta May 9, 2018, 5:18 pm

    these questions are perfect! my boyfriend enjoys talking about deep topics so i am going to ask him these tonight. appreciate you sharing.

  • toni May 9, 2018, 9:43 am

    these are actually very nice. i like them and i will definitely use them with my man. thanks for your help and advices.

  • andrea May 7, 2018, 5:06 pm

    i will bookmark this page and will grab my boyfriend to start real conversation about big topics. i will share this one to my friends so they could deepen their relationships with their guys too.

  • nicki May 3, 2018, 3:23 pm

    a success of a relationship really depends on each other. if you want to avoid a big heartache, learn to get to know your guy by asking him deep questions.

  • aubrey May 2, 2018, 8:36 pm

    these are all great questions to ask. but make sure you and the guy you’re with are comfortable with each other. deep questions aren’t for those who aren’t really into the kind of relationship you’re in or what you plan on having.

  • carolina May 1, 2018, 2:32 pm

    some girls think they already know everything about their man after months or years of being together, but there is actually a lot that needs to be discovered like what shaped them or their personality and life changing events.

  • emily April 30, 2018, 10:43 pm

    wow, i love this and just what i need right now! thank you for sharing these thoughts, i’m ready to try asking them to my boyfriend to get a sense of what the future hold for us.

  • gigi April 27, 2018, 1:24 pm

    i want to be more closer to my boyfriend and asking him deep questions can help me. these questions can also test how compatible we are. he might ask me right back and i am prepared to answer.

  • ayesha April 26, 2018, 7:02 pm

    most of the time, men are really difficult to read and reach. it’s always a good idea to talk to him and both have a great conversation. these deep questions are so awesome, you will have the best time!

  • sofia April 25, 2018, 2:02 pm

    guys are really different from girls. they do not reveal their inner self easily. the deep questions in this article are perfect if you want to reach your guy’s heart but it is very important to build intimacy with him first before you ask him questions.

  • krystal April 24, 2018, 7:35 pm

    being with a man is not always fun and chill. if you want your relationship to grow, make sure you build up on your communication. these deep questions will help you get the right things to talk about.

  • paula April 23, 2018, 2:46 pm

    a lot of couples don’t really get to know each other on a deep level at the beginning of their relationship. thanks for sharing this wonderful article. it is really a must read. these questions will absolutely start the conversation that very few couples ever have with each other.

  • ivory April 20, 2018, 5:28 pm

    this type of deep questions is usually for those who really seek a serious and more personal conversation. if you want to know your man in a deeper sense, these questions are definitely going to be the best you can ask. make sure you’re into the moment and also open to share your thoughts.

  • rose April 19, 2018, 2:26 pm

    asking your guy these deep questions will definitely help you understand him better. it can also help make a more honest connection between you and your partner. thank you so much for posting this article that will let us see our partner’s true self and personality.

  • andrea April 18, 2018, 3:37 pm

    talking about the meaning of life can give you sense of what the future with your man looks like. if he’s all about fun and parties and all might as well think twice. well, only if you are looking for something serious.

  • mary April 17, 2018, 2:12 pm

    i can’t wait to try asking my guy these deep questions and use the information i gather to build direct connection with him. thanks for sharing this very helpful article.

  • khloe April 16, 2018, 3:19 pm

    if you want to win a man’s heart, make him feel that you really understand him in a way that no one else does and one way to do that is by asking him deep questions.

  • hailey April 13, 2018, 1:20 pm

    trying to reach a man’s heart is never easy at first but once you get comfortable with your man, it will be lot of fun. try asking these questions when you think the timing is right, these deep questions are not always welcome given different circumstances.

  • karylle April 12, 2018, 2:38 pm

    i really want to get to know my guy on a deep level, but i don’t know how to start. i am so glad i came across this fantastic article. thank you for sharing the right questions that will help me uncover my guy’s true self and personality.

  • mariah April 11, 2018, 5:32 pm

    there are really those times when you need to get a little bit serious with the type of conversation you have with your partner. and for reaching out to him to a deeper level, these ideas are the best!

  • melania April 10, 2018, 2:25 pm

    i wanted to get my guy talking about personal stuff and this is the only list i’ll need. the questions are fantastic and i am sure he will them interesting.

  • melissa April 9, 2018, 3:02 pm

    asking your guy deep questions is one way to test your intellectual compatibility. i love my boyfriend and i want our relationship to develop and i think this article can help . thank you so much for sharing.

  • maxine April 6, 2018, 1:45 pm

    if you want to get really personal with a guy, asking him about the meaning of life and his purpose. this way, you can gauge how much of a priority you will be to him and you would mean to him now and in the future.

  • viola April 5, 2018, 12:14 pm

    a good communication in a relationship is key. i’m glad that there are so many awesome sites like yours nowadays provide what we need in strengthening those relationships. i really appreciate these tips! thanks!

  • cindy April 4, 2018, 2:57 pm

    if you want your relationship to succeed, you and your partner must be open with each other so what i can say is, knowing how you can communicate well with each other is necessary. both should be good listeners.

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