30 Serious Questions to Ask Your Boyfriend to Form a Deep Bond

If you want to deepen the bond with your boyfriend, here are some serious questions to ask your boyfriend. Try them on your next date night!

serious questions to ask your boyfriend

Hanging out together and watching Netflix is always a great way to chill with your boyfriend. But it’s certainly not the best way to get to know more about him. Of course, don’t hit with these serious questions to ask your boyfriend two dates into the relationship. These questions are best when you’ve been seeing each other for some time.

You want to take it up a notch and really see who this guy is. The last thing you want is to get yourself in a relationship with a guy and realize you don’t really know each other or even want the same things in life. So, this is where the serious questions come into play.

[Read: 50 relationships questions to test your compatibility instantly]

30 serious questions to ask your boyfriend

These questions will help you open your boyfriend up and share vulnerable thoughts and feelings with one another. Don’t assume what your boyfriend is thinking because everyone is different. You need to hear his thoughts come from him, not from your assumptions. [Read: How to talk about your feelings in a relationship and grow closer]

Even though it’s easy to generalize and assume all guys want the same things or feel the same way. If I were you, I wouldn’t read these questions one after another. Pick a couple that you really want the answers to, and ask them when you feel it’s the right time. If not, he’ll feel overwhelmed, and you won’t end up with getting the answers you were looking for.

When two become one…

#1 Do you imagine a life with me? Well… yes? No? It’s important to know what he thinks about your relationship and where it’s going. [Read: What does it mean to be vulnerable? 13 ways you can open up to each other]

#2 What’s the biggest lesson you’ve learned from your past relationships? Every relationship comes with a lesson.

#3 How’s our sex life? What does he feel about your sex life?

#4 Do you see yourself getting married? Do you two have the same future in mind? [Read: What is commitment in a relationship? Do you have it?]

#5 What are you hard on yourself for? Is there something he takes too hard on himself?

#6 How do you describe me to other people? Hopefully, with good words!

#7 What habits of other people annoy you? What are his pet peeves? Everyone has a pet peeve… or two. Let’s find out what his are.

#8 What’s your opinion on marriage and kids? Is it something he wants in the future? 

#9 Do you have any regrets? Everyone has regrets. Though he may not share his deepest regrets, this question will open up the topic.

#10 What’s the best memory you have of your childhood? Get a glimpse into his childhood.

#11 Is there something I should do for you that I’m not doing now? Maybe he wants more cuddles or kisses, who knows.

#12 What’s one mistake you made that turned out very well? Not all mistakes are bad ones. 

#13 What does love mean to you? Do you two have the same definition?

#14 What are the qualities that you love about me? It’s time to hear the compliments.

#15 What did you like about how your parents raised you? How will he want to raise his family? [Read: 41 conversation starters couples should use that are getting serious]

#16 Is there something you need more from the relationship? Everyone has needs; are his needs being met?

#17 Who is your role model in your life? It is his father? Mother? Who does he look up to?

#18 If you could live anywhere, where would it be? Ooo, let’s see where he dreams of.

#19 Are there any fantasies you have you want to try? Oh, we all know this answer. Maybe you’ll be willing to try out his fantasies. [Read: 12 arousing sexual fantasies to try in real life]

#20 What was the first thing you thought when you met me? Let’s see what was going on in his mind.

#21 Have you been in love before? Are you the first? Or his second?

#22 Do you feel you’ve been vulnerable in our relationship? Is there room for growth?

#23 Have I ever hurt you? Well, have you?

#24 How many exes have you had? Not how many people has he slept with. There’s a difference.

#25 What’s your biggest fear for our relationship? Everyone has a fear, what’s his?

#26 How can I be a better partner? There’s always room for improvement.

#27 Ideally, how intimate would you like us to be? Doesn’t mean you need to have more or less sex, but it’s interesting to see what he thinks.

#28 What’s your favorite memory of us? Oh, he has at least one. It’ll be interesting to see what he keeps in his memory of your relationship.

#29 What’s something you’ve always wanted to tell me, but never felt comfortable? Hopefully, he’s comfortable enough to tell you now. [Read: 60 get-to-know-you questions for a new romance]

#30 What do you envision for our relationship? Are you in his future? Where does he see it going?

[Read: Ask your boyfriend these what-if question to grow closer]

Now that you have these serious questions to ask your boyfriend, there’s no excuse. It’s time to go deep!

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Natasha Ivanovic
Natasha Ivanovic is an intimacy, dating, and relationship writer best known for her writings on Kiiroo, LovePanky, Post Pravda, and more. She's the creator and ...
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