25 Deep Questions to Ask a Guy & Turn Any Guy into an Open Book

Guys may be quite closed off but that doesn’t mean there aren’t ways to open him up. There are deep questions to ask a guy to really get to know him.

deep questions to ask a guy

You’re into this guy, but you don’t really know a lot about him. And that makes sense. Sometimes we fall for people before we really know who they are. But now, it’s time to go beyond your physical attraction for them with these deep questions to ask a guy.

If there’s any set of questions that can help you get to know a person better, it’s deep questions. These are the type of questions that can help someone open up more and reveal details about themselves. Most importantly, it will help you build a connection with him by getting to know him better.

Of course, this is only if you want something more serious with him. If you’re only looking for a hook-up, then you don’t need to know what he wants in his future and how his relationship with his mother is!

[Read: Casual dating vs serious dating – What do you want for now?]

How can deep questions help him open up?

Sometimes, people don’t open up because they simply don’t know how to or can’t find the right words. Especially if the conversation is often filled with small talk, it’s hard to open up. So by using deep questions to ask a guy to your advantage, it might help him reveal more things about himself so you can get to know him better.

Whether it’s how he was brought up or his goals, it will give you a stronger sense of who he is.

More importantly, you’ll get to know whether you have the necessary chemistry and compatibility to date or take things further in your relationship. [Read: 40 very deep questions to ask someone before you get close to them]

25 deep questions to ask a guy and get to know him completely

If you’re hoping for something serious to come out of your relationship with this guy, start asking him deeper questions that can ultimately affect your life together.

Also, by using these deep questions to ask a guy, you can also answer them for yourself and find out more about what you want.

Want to know more about him? Just ask the right questions. [Read: The 60 best deep get to know you questions to know anyone instantly]

1. How’s your relationship with your parents?

When you first date a guy, you need to understand him, and also his dynamics with his parents. How do his parents interact with each other, and how does your boyfriend treat his family?

How your partner was raised and how they treat their family reflects who they are, and your future, if you choose to be with them. It also tells you a lot about how they will respect and love you when the time comes. [Read: The 20 qualities in a guy that make him a really good man] 

2. What are you looking for in a partner?

This is one of the best deep questions to ask a guy to get to know what he’s looking for, and if what you both want can be found in each other.

Do they want someone who will be a homemaker, or are they looking for a partner who’s also working? What do they need from their partner? And what do they wish to bring to the relationship themselves? Can you provide these needs for them? [Read: What to look for in a relationship – 23 traits of a happy romance]

3. What are your goals in life?

It’s important to know what a person’s goals are as it gives you a sense of who they are and what keeps them motivated. Is he interested in getting married? In having children? Does he want to finish university? How does he envision his life? Do some of his goals match with yours?

When you want to pursue a relationship with him, it’s important that your significant goals match. Otherwise, this can cause some form of conflict.

4. What do you want from an intimate relationship?

What is he looking for? It’s a tricky question to answer because some of us have no idea what we want. Instead, we go with the flow. This is one of the most important questions to ask a guy just to test your compatibility.

If you both want different things from a relationship, it will cause friction in your relationship, one way or another. [Read: 33 traits and qualities that make a guy a really good boyfriend]

5. What does the perfect day look like for you?

Your lifestyle is another crucial aspect at play when you’re looking to see if you’re compatible. So if a perfect day for him consists of playing video games all day and that isn’t what you have in mind or you’re not comfortable with it, this will be an issue.

We’re not saying you need to find a guy who has the same interests as you, but you need to find at least some form of common ground to spend time together.

6. Have you ever struggled with substance abuse?

Have you ever struggled with substance abuse? This is important to ask your partner. Of course, this doesn’t mean that he’s a bad person if he has had substance abuse issues. However, it can be destructive to you if they’re currently dealing with substance abuse as it will cause damage to your relationship, one way or another.

This question allows you to be aware of all destructive tendencies when the time comes. [Read: Serious questions to ask your boyfriend to form a deep bond]

7. What’s your biggest fear?

Everyone has their own fears, so what are his fears? This doesn’t mean his fears make him a bad or weak person. It’s just interesting to see what makes him scared and if he’s trying to fight his fears.

Everyone has fears, and knowing what those fears are will help you build intimacy and connection. Revealing fears is a vulnerable thing, so that vulnerability can help you connect with each other. [Read: 20 downright strange but true phobias about love]

8. Do you want children?

Before you get serious with someone, it’s essential to ask whether they see children in their future or not. Not everyone wants kids, and that’s okay. But if you want kids and they don’t, this might be a problem. This is one of those huge deep questions to ask a guy and a very important one at that.

If you’re set on having kids, don’t waste your time on someone who doesn’t want children – at least, don’t see them as a life partner. [Read: Why you should run if you see these early relationship red flags]

9. Where’s your happy place?

Where is that one place he goes to when he just wants to be alone by himself and reconnect with his thoughts? We all have a place like that of our own. When he’s having a bad day or he’s anxious, what does he do or where does he go to collect his thoughts and calm himself down?

10. What are you thankful for?

Gratitude is such an important emotion as it helps counter all the negatives in the world. This is one of the deep questions to ask a guy to know what things or people he’s grateful for in his life.

It’s always interesting to see what people value in their lives. Is it money? Their valuables? Or friends and family? [Read: Emotional maturity and the clues that will tell you if someone has achieved it]

11. Are you religious or spiritual?

When it comes to the perfect deep questions to ask a guy, we want to say that it doesn’t matter, but religion usually ends up playing a role in our lives.

We never want to admit it, but religion does play a significant role in our relationships, even if one of you is an atheist. So by asking him if he’s religious or if religion is important to him, you’re testing a critical aspect of your compatibility. [Read: 15 big relationship questions you must answer before the next level]

12. What’s your biggest regret in life?

He may not want to answer this question right away; it can be an emotional and heavy one for some people. But it’s interesting to see what he regrets in his life.

If he does answer this, it means he’s slowly letting you in his world and letting you see even his vulnerability and weaknesses. [Read: The different kinds of regret and ways to deal with it]

13. What’s the longest relationship you’ve had?

Knowing someone’s dating history really gives you a sense of who they are. If someone has never been single and has jumped from relationship to relationship all their life, that’s a red flag for unresolved issues. On the other hand, if they’ve never ever had a serious relationship longer than six months or a year, that’s something to consider as well!

This is one of the deep questions to ask a guy to see whether he’s ever been in a long-term relationship and if they’re capable of staying with someone for years. [Read: 20 questions to ask a guy that’ll instantly reveal who he really is]

14. What’s a relationship deal-breaker for you?

What’s the one thing he would not tolerate in a relationship? We all have boundaries, so what are his? Flaking? Is it lying? Cheating? Chewing with your mouth open?

This will also help you see if there’s something you have that he considers as a deal-breaker. [Read: 17 relationship deal breakers on yourself to watch out for!]

15. Dogs or cats?

Okay, while this doesn’t exactly classify as a deep question, it can still help him open up more. What if you’re allergic to cats, and he has three cats of his own?! You need to know this!

16. What’s the most important thing you’ve learned from your past relationships?

Unless he’s never had any past relationships before, he should be able to answer this. It will give you an insight into how he handles relationships, breakups and if he learned from any lessons.

If someone doesn’t learn from the past, they’re bound to repeat it in the future. So this is one of the crucial deep questions to ask a guy before getting serious with him. [Read: 40 super-important things to look for in a guy before you date him]

17. How would you rank the following: love life, family, career?

Where does he place importance in his life? Is it just about making money and having a career? Or does he value his family above everything? If you take things to the next level with him, you need to know if you have the same priorities in life.

Otherwise, it’s easy to have conflict eventually in your relationship when he prioritizes his work above everything and you don’t. [Read: Love or career? – How to make the right choice]

18. Mountains or beach?

Of course, you can like both, but we usually tend to favor one over the other. What does he think? Is he a beach person or a mountain person?

Do you share the same feelings? If you go on vacation together, how will you decide if he likes mountains and you like beaches?

19. What’s on your bucket list?

We all have a list of things we want to do/see before we die. What does he want to do? And can you cross some of those things off the list together?

It also gives you a sense of how adventurous or spontaneous they are and how willing they are to go beyond their horizons. [Read: Avoid these questions because they will definitely turn your date off] 

20. Morning or night person?

What does he like? Would he rather stay up all night or wake up early in the morning and get a fresh start to the day?

Is he the type to start his mornings early and on a productive note, or is he a night owl that sleeps way past midnight? [Read: How to be more playful and flirty – learn to open up when you meet someone]

21. Do you consider yourself an introvert or extrovert?

Your personalities are essential when testing your compatibility. If your partner is an introvert and their ideal way to spend time is to watch a movie at home, this could be a problem when your ideal is attending a party and socializing.

Even if you’re polar opposites, ask yourself if you can both find a middle ground. [Read: Introverts vs. extroverts – Which side are you on?]

22. What’s your proudest accomplishment?

We all have our big accomplishments that become our highlight over the years. This is one of the deep questions to ask a guy if you want to know more about his goals and passions in life. It also gives you a sense of what he considers success and the story behind that success.

23. Is your career right now your dream job?

Again, another question about career. While we don’t always end up with our dream job, this helps you see his drive and determination to achieve the career he truly wants.

Also, it enables you to know the story behind how he ended up in his current job. [Read: Follow your dreams – All the amazing reasons why it’s worth it]

24. Do you see yourself getting married in the future?

This is one of the deep questions to ask a guy that will give you insight into his intentions for getting in any type of relationship, not just with you.

It can be a massive conflict when you date a guy who has different plans than you do, so this question will literally make or break your entire relationship. [Read: 20 questions to ask each other before getting married]

25. What are three values most important in a relationship?

It will cause friction when you have conflicting values with the guy you’re dating. So by asking him this, you’re seeing if your values align and whether you share some of those values to make a relationship work.

So for instance, one of his values may be shared belief or faith, and you don’t have that same dedication. It might be a struggle later on.

[Read: 10 ways to know if your relationship is worth keeping]

So, what are the best deep questions to ask a guy?

By asking a guy deep questions, you can get to know him better and encourage him to let down his walls. Especially if you’re interested in developing a connection with him, this will test your compatibility and chemistry together.

Unlike small talk or easy questions, this will help you get a deeper sense of who he truly is. So ask away, and use any other questions that have bothered you as well. As long as you keep things casual, and open up to him yourself too, these questions will reveal way more about him than you can imagine!

[Read: 150+ fun and very personal questions to ask a guy and get him to reveal all in minutes!]

Now you have all the deep questions you need to ask a guy and help get to know him better. So do you both have the compatibility it takes to make a relationship work?

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