How do you know what to ask a guy when you want him to open his heart to you in a way he never has before? Getting a guy to answer “normal” questions is one thing… but getting him to open up and truly spill his heart is different.

If you want general questions to ask a guy, this will give you safe questions to ask in any situation.

To open a man’s heart and make him open up to you, you need to consider what questions to ask. I have a list of the best personal questions to ask a guy so that he opens up, reveal information he would never tell anyone else and feel you are a woman who stands out from the rest. In other words, he will see you as “special,” one of a kind, the woman who he trusts.


Men don’t trust easily.

Deep Questions to Ask A Guy: How to Get Him To Open Up

How do you make a man open up and feel warm and fuzzy when he talks to you? These kinds of questions don’t get discussed enough. Why? Partly because men don’t In fact, most men want to date without having to open up. Most men fear opening up and don’t want to seem weird or “weak.”

I have specific personal questions you can ask your boyfriend or a guy you like that will make him feel comfortable talking about an otherwise uncomfortable subject matter with you.

It will make him feel like he can open up to you when you bring up a topic to him that he normally does not talk about and yet somehow feels OK discussing with you.

This feeling will be unique to him. Men are not as used to being open in the way women are; not trying to stereotype. I am a woman, and I know that yes, I am guarded and not always comfortable with my emotions, but men are generally even less comfortable and less used to feeling comfortable.

So when you are a woman who can make him feel truly comfortable and open it will make you stand out in his eyes.

Further Reading: 21 Intriguing Questions to Ask a Guy You Like



Deep Questions to Ask A Guy: How to Get Him To Open Up

  • Don’t be too sudden with how “deep” you take things
  • Don’t be too persistent in terms of him opening up (as in do not demand he open up; allow him to be free with his expression)
  • Don’t assume anything or blame and attack if he says something you don’t like

These “golden rules” will help you relate to him and show you a path where he is going to be as comfortable opening up with you as possible.

I am going to give you some intense, heartfelt questions to ask in ONE situation. What situation? If you already know him and he is comfortable with you. If he is not comfortable with you, these questions will make him shut down and not feel open around you. But if you know him well and ask them without any sort of judgment, they will make him open up in a way that will shock you.

  • How often do you cry?
  • Do you ever have nightmares?
  • What’s the most traumatic thing you have been through?
  • Are you a hopeless romantic?
  • Do you think love is actually real?
  • Do you think it is fair that some people die young even though they are good people?
  • Do you believe God exists?
  • What is your biggest fear?
  • How often do you think about death?
  • Have you ever wanted to die?
  • What is your biggest regret?
  • Does anything haunt you?
  • Tell me something… what is a secret about you that no one else knows?
  • How often do you think about your past?
  • What is your #1 proudest moment of your life?

Further Reading: Good Questions to Ask Your Boyfriend


Give Him A Safe Space

Deep Questions to Ask A Guy: How to Get Him To Open Up

The above list is so personal he might be resistant to your questions at first. But if you let him have a “safe space” to open up, this will change his entire perspective on you. He will open his heart to you in a way he never has to anyone else before.

When he answers these questions, let him speak. Don’t jump in with your opinions. Just let the words flow out of him. Let him be himself—his full self—and don’t be judgmental at all.

When a man trusts you enough to be this open, amazing things happen.

He will definitely think you are “rare,” the kind of woman he can open up to… unlike the countless others who seem to judge him and not care about what he has to say. This is huge when it comes to opening up… men get shut down when they

So let yourself be his “sanctuary” from the cold, cruel world he fights so hard to deal with.

And let me know how these questions go—I am rooting for you!!!

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