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

If you want to get to know someone, the best thing is to ask questions. But what deep questions to ask a guy to make him open up? Well, read on!

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.

Get to know who he really is and what he wants in his life. He can be the hottest guy you’ve ever seen. The chemistry between you two could rock the earth, but there needs to be more beyond that.

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?]

20 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. 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? Ask the right questions.

#1 How’s your relationship with your parents? When I first started seeing my partner, my dad told me to meet his family and see their dynamics.

How do his parents interact with each other, and how does my boyfriend treat his family? How your partner was raised and how they treat their family is reflective of who they are and your future if you choose to be with them. [Read: The 20 qualities in a guy that make him a really good man] 

#2 What are you looking for in a partner? Do they want someone who’s going to be a homemaker, or are they looking for a partner who’s also working? What do they need from their partner? More importantly, are you someone who sees themselves doing those things for them?

#3 What are your goals in life? 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? Of course, some of his goals are only for him, but having kids takes two people.

#4 What do you want from an intimate relationship? What is he looking for? It’s a tough question to answer because some of us have no idea what we want. Instead, we go with the flow. This isn’t bad, but it’s important to see if there’s something specific he has in mind and if it aligns with your needs. [Read: 25 traits and qualities that make a guy a really good boyfriend]

#5 What does the perfect day look like for you? When I met my boyfriend, I didn’t know his perfect day would be napping and watching TV. And I’m the complete opposite. Of course, you can make things work, but it’s interesting to see if you two have a similar lifestyle in mind.

#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 if he has had substance abuse issues, he’s a bad person. But, it does mean there’s a chance for him to relapse, and you need to be aware of that if you’re in a relationship with him. [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. 

#8 Do you want children? Bingo! 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. If they’re unsure, that’s a different story. [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 with himself and reconnect with his thoughts? We all have a place like that of our own.

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

#11 Are you religious or spiritual? Better yet, are you religious or spiritual? When it comes to the perfect deep questions to ask a guy, I want to say that it doesn’t matter, but religion usually ends up playing a role in our lives. Do you come from different religions? Is it possible to live together with both, or is conversion something he would like his partner to go through? 

#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.

#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 had jumped from relationship to relationship, that’s a red flag for unresolved issues. [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 is the one thing he would not tolerate in a relationship? We all have boundaries, so what are his? Is it lying? Cheating? Chewing with your mouth open?

#15 Dogs or cats? What if you’re allergic to cats, and he has three cats of his own?! You need to know this! Plus, we all know what the right answer is… dogs.

#16 What’s the most important thing you’ve learned from your past relationships? If he’s dated before, then he’s experienced what it’s like to be in a relationship. That means he has learned some things. But has he really? If someone doesn’t learn from the past, they’re bound to repeat it in their future. [Read: 12 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?

#18 Mountains or beach? Of course, you can like both, but we usually tend to like one over the other. What does he think? Is he a beach person or a mountain person? Do you share the same feelings?

#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? [Read: Avoid these questions because they will definitely turn your date off] 

#20 Morning or night person? I used to be a night person, then I started to realize how amazing mornings are. 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?

[Read: How to be more playful and flirty – learn to open up when you meet someone]

Now you have all the deep questions you need to ask a guy and help get to know him better. But, remember, he also should get to know you.