Questions To Ask A Guy To Get To Know Him Deeper

Guys are not usually an open book when it comes to trying to get to know them on a more intimate level. When asking them questions to this end, many new boyfriends will try to get away with as few words as possible. 

That makes the challenge a bit more complicated but not impossible. It just requires digging a little deeper with questions that need a bit more introspection and explaining instead of merely coming up with a witty response. 

Let’s see if we can dive into some of the tough questions that men might put time and forethought into enough to develop a genuine connection.

Deep questions to ask a guy

Couples can develop feelings at the beginning of their dating period based simply on attraction, small talk sort of conversations, and enjoying each other’s personalities. 

Still, there comes the point where you recognize liking someone you don’t know a whole lot about, at least not who they are authentically. 

You can’t continue to establish a bond based merely on what you know on the surface. The best way to grow closer on a more intimate level is to ask questions and not those that he can respond to with quick wit. That could be asking about your partner’s past, previous relationships etc…

Bonding questions are those that are more in-depth, requiring forethought and almost a story to explain the answer. That includes asking if he has a girlfriend etc…These bring individuals into a more vulnerable state, offering details about themselves that might not fall under usual circumstances. 

They help the relationship move towards a more substantial connection. That’s because you’re growing more familiar with who he is as a person. This is usually more challenging for guys because they don’t tend to open up voluntarily. 

Plus, conversations when dating in the earlier stages, again, border more on small talk, leaving potential new partners unsure of how to broach specific topics. 

Approaching him with more profound questions relieves his uncertainty on how to have the more challenging topics. You will also be able to assess whether the two of you are suited for each other with the interaction and the answers to some of the tough questions. 

If you’re moving toward something more serious, this is the first step in that direction. It’s because these questions can impact how you view a future with this person. 

And if he doesn’t do it, you should carefully consider how you might respond to the same questions so you can figure out what you will eventually want. Some questions to consider asking a potential serious boyfriend.

What’s your relationship like with your parents

How a family interacts will speak to the adult child’s behavior in numerous ways. This is a priority question if you want to understand a guy you’re dating. 

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Not only how he and his parents get along, but how the parents get along with each other is critical, and how he overall treats the family. How a child is raised, and the parents’ influence on them will ultimately impact the individual’s future and who they become. 

If the home were loving and healthy, with the parents exhibiting a strong, secure bond, the man would also strive to have that with his future wife and children. If you don’t date that person often, or you need to ask him some questions to get to know him deeper over text, make sure you give him the time to respond.

That’s because some questions are a little bit confusing for some. By flirting over text and showing your interest to know that man better, you’ll build stronger conversations.

Suppose the man hesitates to answer the question or has difficulty discussing the issues. In that case, it might be a good idea to consider working through this component of the relationship with some counseling to help him deal with what appears to be family trauma. That way, you can move forward healthily.

What do they need from a partner?

If your relationship seems to be progressing to the next step, this question is essential. The two of you need to ensure that the things you need and desire in a partner, the other person has the capacity to give. 

Does each person want to have a full-time career outside the home, prefer a self-employed career from the house, or would rather be a full-time carer to the household? 

What does the boyfriend expect from his partner, someone who works or doesn’t? What does he intend to contribute to the partnership? Is that enough for you, or did you have other expectations for a mate?

This question aims to determine if this is the right guy for you. You could find that you have someone who expects their significant other not to have a career of their own, something you didn’t know until you asked the question. 

Perhaps you’re thriving as a self-employed freelancer. How does that work? Do you give it up for love? Much to consider. Also, you can ask romantic questions such as:

  • Do you have dating profiles, actually?
  • Do you think social media, like Facebook and Instagram, can affect relationships?
  • What’re your expectations from a working wife?
  • How can you take care of your partner when he feels sick?
  • How do you feel when you see your girlfriend with another guy?

By asking these questions, you’ll get an idea about the things that guys love but won’t tell you. Additionally, you’ll know that person better.

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How does he define a long-term committed relationship?

This is a bit of a tricky question because it could put the kibosh on the whole relationship with merely one answer. Some people have the mindset that they eventually hope to marry. 

Others are dead set against ever marrying. They don’t believe you need that “piece of paper” for the world to know you are a couple. 

That doesn’t mean that as things progress. One or both of you could change your mind, and it will work out fabulously. But during this particular question and answer session, this will cause contention if the answers are incompatible.

It’s vital that the two of you not make any rash decisions based on a single conversation, like breaking up over an answer you don’t like. 

If you have a connection and grow together with a strong bond, people change. Someone who was adamant against marriage could have found the one person that made that thought process different for them, allowing for a wedding. 

Don’t be hasty in walking away unless a lot of the responses to the questions are just way out of sync.

Other than that, it’s a good idea to see how your future partner will support you during difficult times and life challenges. If he doesn’t care at all, you know that you can’t count on him.

Tell me about a perfect day for you

You can use so many funny questions to ask someone in order to get to know him better and deeper. But this one is a good choice because it can help you discover the inner feelings of your partner or your crush.

Everyone will have a different answer to this, and that’s the correct answer. A perfect day is unique for all of us. But you’ll find with couples; that there are often common denominators, they share that make them sometimes enjoy their perfect days together. 

If your current partner has details of a perfect day, you can’t find any common ground on, that could possibly create a challenge in the relationship. Perhaps for this man, the best day would be sitting at home all day gaming on the computer. 

That’s great for your guy. It might be a stress-relieving hobby that he enjoys in his downtime. But if it’s something he regularly does and anticipates that you’ll participate in your free time. You might need to have a conversation to look at a compromise. So you can each have a good time while you’re with each other.

Is there substance abuse that needs to be addressed?

If you want some dark questions to ask someone, this is a good one. But, make sure you read behind the lines and not just trust what they say. Some people have criminal records, and when you’re dating them, you should take things seriously and search for your crush’s details online.

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You won’t get a forthright response to this question if there is. Most people struggling with substance abuse or drug addiction will not admit that to another person unless they’ve reached a point where they want to seek help. 

What could happen, and you need to be exceptionally prepared in this situation, is he could become agitated, defensive, and lash out about you asking. That will be your answer.

You will need to decide if this is something you want to take on or if you want to cut ties and move on. Dealing with someone who has any sort of addiction is heart-wrenching, draining, and debilitating, any word you can think of that defines sucking the soul from your body every day. 

You personally cannot change this person; you will not be their miracle. That has to come from within. And sometimes that never arrives, or it comes after death reaches out to them first. 

No one has the capacity to make the individual seek assistance. They have to want to get help or stop. This would be a dealbreaker for anyone who has already experienced it. Consider that before you take it on.


When you find a new dating match, that starts to grow more serious. But you still don’t know much about the guy, it’s time to learn. Men can sometimes be closed off with personal details or, more so, with becoming vulnerable. 

It takes letting them know they’re in a safe, non-judgmental space where they can be open and honest and feel free to express themself openly.

If you choose to spring some deep questions on your boyfriend to get to know him better, don’t put him in the hot seat. It shouldn’t be like an inquisition. But in a more casual, comfortable setting where he doesn’t feel put on the spot, maybe settled in with some snacks and drinks cozy on the couch. 

The conversation should be easy and carefree and not like you’re watching for the slightest wrong answer. Deep questions don’t have a wrong answer. 

Each person only has their own personal answer. How you react to that or feel about it should be saved for after you’ve had time to think over all the answers collectively when the evening is done. 

You might find this isn’t the mate for you, and he might agree. But you should find out before you develop a serious commitment.

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