Bringing your relationship to a deeper level has always been a tricky task. Especially if you have a boyfriend that is totally clammed up about talking about just about anything personal.
You’d be surprised to discover how many men are actually insecure when it comes to answering personal questions.
In the past, I definitely had some difficulty with how I thought I appeared and sounded towards women.
Now, after multiple relationships and different experiences with many types of women (shy girls, quiet girls, forward girls, girls who dance on tables, etc.)… as well as being asked and responding to just about every question possible, I’ve become very comfortable discussing my personal thoughts, etc.
At this point, I’m completely comfortable striking up and having any kind of conversation with just about anyone to get to the heart of the person. In fact, it doesn’t even cross my mind anymore.
The issue is, there is no such thing as a real relationship without really knowing someone.
So how in the world do you go from small talk, to really getting to know someone in order to make a more emotional and honest connection?
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Well, this article is organized into specific categories so that you know exactly what to say in every “level” of connection.
You will find mild personal questions that are “safe” to ask and won’t offend anyone unless they’re insane, mild questions for when you are getting to know somebody, high level questions for when you know somebody well and want to go deeper, and finally, super personal questions for when you’re either in a relationship or seriously pursuing one.
- Starting Out Personal Questions
- Medium Level
- High Level
- Super Personal (Maximum Level)
Quite simply, coming from a man’s perspective, emotions can be awkward for men.
I know that growing up, crying, for me, was a “no no…” and so was any sort of complaint relative to pain or emotion.
For example, when I struggled with depression, I had to “get over it” while my sisters saw a slew of doctors and therapists.
The honest truth is that once a guy sees there is no judgment from you he will get more and more comfortable. And if he starts sharing very personal stories with you and sees that you don’t look at him strangely, he will share more. And as this process continues, he will become more and more comfortable with you until he actually shows his “full self.”
I’m going to give you some personal questions you can throw out there to elevate your relationship, as well as crack his tough, guarded exterior.
Use whichever questions you see fit. Some are obviously a little more serious than others, but nonetheless…
I recommend, starting small- don’t scare him off. A, what I would call a “premature personal question” can be a deadly mistake, it can even come off as intimidating, or rude. This is very important.
Categories of Questions
As I mentioned, the article is organized into categories. This is because of what I just mentioned… how important starting off small is.
Icebreaker Personal Questions To Ask a Guy:
- Where are you from?
- Do you have any siblings?
- If from somewhere different than you, what was it like growing up there?
- What does/ did your father or mother do for work?
- Do you have any interesting family members?
- What do you do for work/ aspire to be?
- Where do you want to be in 5 years?
- Have you had any crazy girlfriends/ relationship experiences in the past?
- Do you have a favorite band/ type of music and why?
- What’s your favorite hobby?
Keep In Mind
These are simple very base level questions. The key is that usually, the guy will respond with similar questions about you, and you’ll definitely gain some comfortability, just from the fact you have an idea of who he is and an inkling about his past.
Medium Level Personal Questions To Ask a Guy:
- What kind of kid were you in school?
- If you could be anything what would you be?
- Have you ever been severely injured?
- Serious accidents?
- When was the first time you liked a woman?
- Who is your celebrity crush?
- What’s your biggest pet peeve?
- What is your favorite/ least favorite type of woman?
- If you could have any superpower, which one would you have and why?
Keep In Mind
These questions take it a small step up, nothing too personal, but definitely above asking whether he has a sister or not. Also, you can tell a lot about someone from their injuries. What if he was a soldier, a professional or college athlete? It’s also good to ask about his type, or pet peeves, because then you know if he’s even going to be a match or not. if you hate what he says, don’t react, just understand who he is and who you are.
See if you align naturally. And if not, it’s no one’s fault. Don’t take it personally.
Not everyone is meant for each other! This is obvious, I know, but I will elaborate on this more later on.
High Level Personal Questions To Ask a Guy:
- Have you ever gotten into trouble?
- Have you ever gotten away with anything illegal?
- What is your favorite way to make love?
- Do you have any kinks?
- What’s the craziest thing sexually you have ever done?
- Do you watch porn (surprise, all guys do!)
- Who’s your favorite porn star?
- Is there anyone on this world you would be happy to see dead?
- Do you have a good relationship with your parents?
- What’s the best memory you have from childhood?
Keep In Mind
These questions are definitely going to cause a reaction, so you should have a grasp on what he’s seriously uncomfortable with before you ask. For example, when I was younger and “fresher” on the dating scene, there were times I’d shut down and get embarrassed about anything sexual, but if done right it really breaks the ice.
We’re all humans, we all have our “needs!” Also, for a man, there is definitely this weird thing about lasting forever and being the “best” in bed in addition to a massive fascination with “size.”
You might be surprised to know that sometimes men are more insecure about sex than women. This might sound insane but it’s true. These types of questions will open a new door. And yes, they are definitely quite personal but hey, you might dig the same stuff without even knowing, so take a shot!
Just remember, don’t come off too strong, it can easily be done candidly to smooth out any possible hiccups.
I find coming off as “thirsty” is a no go for both men and women. Thirsty basically means coming off as either overtly sexual to a point where it is not reciprocated and the woman keeps persisting, or having an air of desperation (which is basically trying too hard).
Sorry for being so blunt, but this is honestly how most men think.
Super Personal Questions To Ask a Guy (Maximum Level):
- What’s your deepest sexual fantasy?
- Have you ever had a loss of someone close to you?
- What is something no one knows about you?
- What is your true nature, do you have a hidden side that no one would expect?
- Have you ever gotten angry?
- Have you ever been arrested? for what?
- Have ever hurt someone, or been in a fight?
- Have you ever had a history of drug use? Or do you know others that use?
- Worst day of your life?
- Best day of your life?
- Biggest lie you’ve told?
Keep In Mind
These questions are pretty serious. You never know what someone’s been through, and I’m sure I’ve surprised a few girls in the past. A few girls have definitely surprised me! This will rip the cover off the proverbial book and really expose who he is.
When You Get Close You Might Be Surprised
I have a close friend, who is very successful, handsome, and newly married. If I walked up and told you he had been to prison for assault for beating someone up in a fist fight, you would call me a liar, but it’s a fact he regrets.
He has a bad temper, and has had issues with it in his past. He’s still a great father, and amazing friend. Learning about loss can also really help you decipher his character.
You might assume, “well he’s quiet and never mentions his mother because he doesn’t like opening up to me”, but then you find out she had passed away from cancer and suddenly it all makes sense. You would never know this unless you’re really close.
These are very serious topics for anyone to talk about, and it truly takes trust to reveal this kind of information. But if you can comfortably talk on this level then you have really reached the pinnacle of personal connection.
These questions will make any man with a bad past squirm, trust me! But if you come off as cool and respect his honesty, there’s not much else he’ll ever feel uncomfortable talking about. A sketchy or traumatic past, regardless of who you are now, is always a hard thing to talk about.
You can never judge a book. Life is a crazy roller coaster full of ups and downs, I recommend picking up a guy on his up swing!
Getting to This Level is Rare
These questions will definitely give some insight into who you’re dating or the man you’re interested in. If you’re able to get to those “high level” questions you’ve definitely got a real close and personal relationship, which is a rarity.
The fact that it is a rarity should show you that not being able to connect on this deep a level with everyone doesn’t mean you’re bad at connecting. It’s not “normal” to be this comfortable with someone! So when you do reach this level of connection, it’s special.
Now, earlier, I mentioned I would elaborate on how not everyone is a good match and how everyone has their own type. Quite simply put… not everyone is compatible.
Frankly, many people are too wrapped up in their own heads to function in a “real” relationship. Sure, you can date and have official relationship titles… but having a true, personal connection requires trust and the ability to step outside your own head in order to truly listen to the other person.
Give Him Space To Answer And Just Listen:
When you have some idea of what you want a man to reveal to you, you might be disappointed when he does not say what you want him to say. But imagine how horrible this would feel to him if he knew that his responses disappointed you?
Don’t have expectations; simply be present in the moment.
You must be a good listener:
This is very important: if you want a man to open up to you, you must be a good listener.
The good news is that being a good listener is the easiest thing in the world. The thing is, being a good listener isn’t so much about what you do, but rather, what you don’t do …
- You don’t have expectations of what you want him to say
- You don’t get upset about things he says
- You don’t make what he’s saying about you
- You don’t judge or attack or argue with what he’s saying
- You don’t try to use being a good listener as a way to impress him
So what do you do?
You give him space to say whatever he wants to say (or not say) and you simply be there with him in the moment as he’s talking.
That means you’re not caught up in your head thinking about what you want to say next. You’re not thinking about something else. You’re not eager for him to say something that makes you feel good.
No, you’re out of being caught up in your mind-chatter and simply have your attention on him, giving him space.
When you do this, he will feel like it’s safe to open up to you and he’ll feel that you will truly hear what he’s saying.
When you give someone your full attention and space to speak, it can be incredibly healing for that person and create an extremely powerful bond.
In this modern day of distraction, it is also incredibly rare… so when you can really listen to him with your full attention and really giving him space to be as he is, don’t be surprised if he starts to feel a very deep connection to you like he’s never experienced before.
What if a guy is quiet?
The super closed off guy could be annoyed (most likely at his own inability to muster up an honest response) or even shut down more because of his own insecurities.
Someone like this is probably not for you. Is that bad? Does it mean something personal about you? Absolutely not. Does it mean something personal about him? Absolutely not.
All it means is that you are not a good match. Nothing more, nothing less.
I’m definitely guilty of being a closed trap in the past, but some girls somehow just get me talking. Some people are right for each other and some people aren’t. I know this is painfully obvious, but i just need to stress this so you don’t think you’re in the wrong.
Being yourself is key, and I recommend asking questions you’d be comfortable with being asked as starters, and not asking ones you feel are maybe too touchy at that moment.
Remember: We Are All Humans
People are just that; people. We are all flawed to a certain degree, and probably have all hit a wall or two, or at the very least a road bump. Take a deep breath and relax.
All good things come with time and patience, whether that be you find out he is not the right one for you, the exact opposite of what you are looking for or your relationship deepens and you find out he is the guy for you.
Essentially, getting to know someone is the first major step in a relationship. If I can be candid with a woman, my intended future will be bright and happy.
Don’t judge, and always be inquisitive. You never know what you might find out!
Want even more question lists to ask?
- Questions to ask your boyfriend – these are excellent to ask your BF and help you understand him better.
- Questions to ask a guy – these are perfect for any situation with a guy
- Truth or dare questions – these questions are ideal and fun for any situation. And work really well for group scenarios!
- Never have I ever questions – these are also fun and work well for groups!
Even more great questions to ask him:
Want to find out whether the man you are with loves you or not? 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…