Why does anyone date or enter a relationship? Is it just sex? Of course not (well, maybe for some people but not most!).
For most, a relationship is about getting to know someone on a deeper level!
A huge problem many women face is their man won’t open his heart . He’s committed but refuses to “let her in,” get emotional and be “raw and real.”
You can only do this by truly getting to the heart of who a person is. This article is going to give you questions to ask your boyfriend so that you can reach his heart.
You’ll get all types of questions. These range from deep, personal questions to funny questions. You can pick and choose the ones you like that you think would make sense for you to ask your boyfriend.
I am going to give you everything you need to get even a guarded man opening up and spilling his heart to you.
Take The Quiz: Is He Losing Interest?
Trust me. Questions can be a way to open his heart and get to know him in a way that makes your heart melt. Your heart will melt when you see that your boyfriend is a human being underneath the male bravado and false pretenses of “being a man.”
Yes, gender stereotypes and social norms have shifted dramatically in terms of “equality,” but men still feel pressure to “be tough” and not express how they feel . This is why your questions will open the floodgates to his heart.
Also remember… not all men are the same. What works with one man might not work with your boyfriend. You know him and should be looking at these questions and assess whether they align with his nature or not.
This article is organized with the best questions first. These include a psychological explanation behind why they work. Then later you can find deep questions, personal questions, childhood/upbringing/past questions, philosophical questions (view on the world, life, etc.), romantic questions, emotional questions, sexual questions and fun questions.
Watch The Video: The Best Questions To Ask A Guy (And Why They Work So Well)
Best Questions: Top 13 Questions
#1: What’s something surprising about you that no one would guess?
The word “surprising” is a key part of why this question is so important. It means he doesn’t have to feel awkward about bringing up something that might be “out of character.” You’re giving him permission to drop his “social role” he plays most of the time.
He plays this “role” of who he is to the outside world… most men do. But most men don’t take “mask” off until they meet someone special. Let him reveal parts of himself slowly and he will get comfortable with you; more comfortable than he is right now. When he feels comfortable he will reveal more and more.
#2: What’s your best memory in life?
The purpose of this is to get to know his past to understand his present. In other words, understand what experiences have shaped him and molded him into the man he is today. This might even make you feel more understanding when he exhibits a tendency you do not like. And this might give you a better appreciation for who he is. And if you have an appreciation for who he is, guess what? He feels this appreciation. And most men desperately want to be appreciated.
#3: Last time you felt fully free to be yourself?
All men want to be seen for who they are and loved for how they are not who they think you want them to be.
#4: Has a song ever made you cry? If so, which one?
This opens up an important topic: emotions. Specifically, expression of emotions. If he is comfortable telling you this, do not go overboard and start asking follow up questions. Just listen to his answer and be aware of the fact that expressing something this vulnerable is not always easy… especially for men. Yes, being vulnerable is not easy for anyone but it’s typically harder for men who are historically expected to be “strong.” If he has cried from a song this gives you insight into his nature. It means he is certainly emotional and sensitive, which is a positive trait (since sensitivity is what men often try to avoid because it’s perceived as weak… but a lack of sensitivity makes a man unable to fully engage in an emotionally fulfilling relationship). So, if he is able to experience this kind of emotion there is a good chance he can feel deeply.
#5: Are you “ocd” at all? Or, do you have any strange tendencies?
This opens the door for you to discover his weird quirks. For example, does he wash his hands all the time? Does he have any peculiar things he needs to be neat? Or need to have his space organized in a specific fashion? Or is he messy and chaotic? All important things to know!
#6: Best lesson you’ve learned in life?
His answer will show you what he values. If his lesson is something like, “don’t do this, or you will get screwed…” it means he leans toward a more victim mentality. But if he mentions something where he emphasizes personal responsibility or a consideration for others (such as… always be fair to others never judge a book by its cover) it shows he might be a more “evolved” person in terms of having a tendency to consider others not just himself.
#7: What was your childhood like?
If he mentions his parents or anything for that matter, just listen. Hear him. If he mentions painful memories, listen. If he mentions happy memories, listen. Letting him talk will take him to different places and start remembering different things. This will make him open him to you even more than he expected! And if he opens up to you more than he expected to, he will tell himself, “woah! I feel comfortable with her!”
#8: Do think you are good at standing up for yourself?
If he says, “no I am too nice” or “yes, of course!” both answers can tell you a lot. If he believes he is too nice he probably has some kind of resentment that he has not stood up for himself. And if he says of course, he might feel he has to put on a tough guy act.
#9: Biggest fear?
His biggest fear will give you major insight into what keeps him up at night. This is at the center of a man’s heart. His biggest fear is going to be what drives him to keep pushing in the world. He might not admit his true fear but what he says will give you an indicator of what he thinks should be his biggest fear.
#10: What makes you angriest?
Remember… asking a man about anger is not something that you will want to judge him for. Instead, listen with an open heart and mind. Anger often masks sadness and frustration. So don’t judge him just listen and see what his “hot buttons” are.
#11: What is your favorite animal/pet?
I judge people if they hate animals. But it’s not likely that he will reveal this to you if he does. But still, if you find out he is an animal lover it’s a good sign of his genuine, good nature.
#12: What’s your most embarrassing moment? I will tell you mine if you tell me yours. I’ll even go first.
Being upfront about your own embarrassing moment is key here. If you initiate and tell something truly embarrassing you set the tone of the conversation. He will reveal the same level you reveal. If you go for it and expose something intense that he probably did not expect, he will most likely do the same!
#13: Do you know that I would never judge you?
This creates a safe space for him to open up. Judgment is deadly. If you make him feel judged, even a tiny bit, he will never open up to you or feel truly close to you. If you say and mean this, it makes it possible for him to actually let you “know him.”
Fun Questions To Ask Your Boyfriend:
- What is your favorite video game?
- What is your favorite movie?
- What is your favorite song?
- When do you feel happiest?
- Favorite song to dance to?
- What’s your idea of a perfect day?
- What’s your favorite scary movie?
- Are women insane?
- Have you ever played Battlefield?
Deep Questions To Ask Your Boyfriend:
- What is your relationship with your father like?
- Do you want to be a father (if he is not one already, obviously)
- What is the most important aspect of life?
- Does money matter to you and why?
- Would you be happy if you found out you could live forever?
- What do you think happens after we die?
- How often do you cry?
- Do you think you are an emotional person?
- What keeps you up at night?
- Do you have a hero?
- Do you want to be a hero?
- How often do you think of your past?
- Is the future something that scares you?
- Are you afraid of getting old?
- Do you think about your past often?
Personal Questions To Ask Your Boyfriend:
- Last time you cried?
- Do you feel like your life is meaningful?
- If you could change one thing from your past, what would it be?
- Biggest lie you ever told?
- Have you ever stolen?
- Have you ever stolen another man’s girlfriend?
- Ever cheated on someone?
- Ever thought you were in love but realized it wasn’t love?
- Sickest thought you’ve had?
- Weirdest experience of your life?
- Most scared you’ve ever felt?
- Darkest lie you’ve told?
- Do you like being in charge or do you like people helping you?
- What’s your greatest fear?
- Who is your greatest enemy?
- Do you want children? (Assuming he doesn’t have children)
- What’s your #1 dream in life?
- Name 5 things you like about yourself.
- Name 5 things you dislike.
- How often do you judge others?
- Do you enjoy being silly?
- Have you ever felt truly understood?
- Do you feel warm butterflies ever when we cuddle?
- What made you realize you truly were in love with me?
- What did you think of me when you first met me?
- Am I different than you first expected?
- Do you believe in soul mates?
- Do you think astrology is crazy or real?
Questions About His Childhood / Upbringing / Past:
- Proudest moment?
- Most ashamed you have ever been in your life?
- What was your childhood like?
- Did you have a close relationship with your father/mother?
- Do you have any major regrets and if so why?
- How did you spend your time off school as a kid?
- Did you go to church or celebrate any religious ceremonies?
- Were your parents strict?
- Do you think you would do anything differently than your parent when raising a child?
- Worst childhood memory?
- What were you like in high school?
- Did you enjoy school?
- What did you want to be when you “grew up?”
Philosophical Questions (view on the world, life, etc.):
- Is love real?
- Does life even have a purpose?
- Do you believe in God?
- Do you think we are living in the Matrix?
- Do you believe evil exists?
- Have you ever felt the presence of a paranormal spirit?
- Do you think a heaven exists?
- If you died tomorrow where would you go, in your opinion?
- What is your weirdest paranormal experience?
- Do you feel strongly about any political party?
- Can you ever truly know someone?
- Do you believe in reincarnation?
- Do you think sociopaths exist?
- If you found out you were going to die tomorrow, what would you do?
Sexual Questions To Ask Your Boyfriend:
- Weirdest “fetish?”
- Most turned on you have ever been?
- Worst sexual experience?
- Weirdest sexual experience?
- Have you ever pretended to be turned on when you weren’t?
- Biggest turn off?
- Have you ever known a woman faked an “O” but did not tell her?
- Do you think it’s weird for a woman to be in control?
- Do you enjoy being in control?
- What is your biggest turn on, ever?
- Wildest fantasy?
- Do you ever “do yourself” alone?
- Do you enjoy porn?
- What kind of porn do you like?
- Does it matter to you that porn is clearly fake?
- Do you think women overestimate how much men value sex?
How Do You Feel When He Opens Up?
OK, now you have a great list that you can use. But is there anything else you need to know? Yes.
Does it make you feel warm and fuzzy when he opens up to you? But you feel awkward or uncomfortable with “emotional” conversations so you dance around topics and never go beneath the surface?
Forget about how you feel when he opens up and focus on him and how he feels. If you want him to open up for your own personal benefit this will rob him of the experience of opening his heart to you. Trust me on this one.
Now, one point to note is… if he is reluctant to answer these questions and seems closed off, he might be losing interest. Take this quiz to diagnose whether this is taking hold in your relationship (do this before it’s too late; he’s still your boyfriend now, so trust me… you want to figure this out before he ends it.)
Take the quiz: Is He Losing Interest?
I know it might sound weird and confusing but it’s actually simple: men don’t want to open up unless you actually want them to. If you want him to open up because it will make you feel better or make you feel like he is connecting to you, forget about it.
He will feel this energy and shut down emotionally.
If you want him to open up…
Realize that how you ask questions is as important as the actual question you’re asking.
If you have a judgmental vibe, no question you ask will be helpful and will only be hurtful.
Don’t judge. Let him talk. Let him be.
And you will see a new man in front of you.