35 Thought-Provoking Questions to Ask Your Boyfriend for a Deeper Connection

If you have ever played Twenty Questions, you’re probably familiar with how it can be a great icebreaker and help people get to know one another.

But with your boyfriend, you may have experienced moments where you run out of things to talk about. 

It's normal for your conversations to hit a lull from time to time.  

That’s why asking incisive questions can help keep things interesting, strengthen your connection, and help you learn more about one another.

Don’t know what to ask him?

We have you covered with some thought-provoking and unique questions to ask your boyfriend to deepen your understanding of each other and keep your relationship fun and fresh.

What's In This Post:

What Are the Benefits of Asking Questions for Your Boyfriend? 

Even if you and your boyfriend have been together for a while, you might be surprised at the new things you learn by asking intentional questions.

It will allow you to connect in new ways and talk about things you have never thought to share. 

You don’t have to read questions off a list. Just choose one that speaks to you and incorporate it naturally into a conversation, letting it go where it will.

Here are a few more benefits of asking your boyfriend questions:

  • Share memories and important events
  • Talk about meaningful people in your lives
  • Be vulnerable and intimate
  • Explore the future of your relationship
  • Have fun talking together and learning about one another’s likes and dislikes

35 Questions to Ask Your Boyfriend

If you want to get to know your boyfriend better, it’s time to ask some meaningful questions.

These good questions to ask your boyfriend can help you learn more about one another and get closer.

1. What makes you feel loved? 

This question can be helpful both in learning more about your boyfriend and how to help him feel your love and appreciation.

It could be something as simple as cuddling on the couch at the end of a long day or something more complex and involved.

2. What is something that most people don’t know about you? 

This is one of those questions that could become playful or deep, depending on the answer.

couple sitting outdoors Questions to Ask Your Boyfriend

Maybe he’ll share a profound secret, or perhaps he will tell you a sweet childhood confession. Either way, you learn something new about him.

3. Who is your best friend, and how did you meet?

You might already know his best friend, but it is great to learn more about their relationship and the things that they have been through together.

Clearly, the person is important to him, so it is great for you to understand exactly why.

4. What are some things that get on your nerves? 

As your relationship develops, you will learn about one another’s pet peeves and how to avoid getting on one another’s nerves. But it can also be valuable to learn why a particular thing bothers your significant other.

5. What is the wildest thing you have ever done?

Don’t be surprised if the answer to this question makes you fall more in love with your significant other.

Or it might just make you laugh. Either way, you get to learn about a time in his life when he was impetuous, wild, and uninhibited.

6. What is your favorite meal? 

Meals have meaning for us. Maybe it’s an integral part of his culture, or he has fond memories of his mom making it for him when he was sick.

Either way, you get to learn something important about him and how to make him feel better after a tough day.

7. What was your most embarrassing moment? 

We have all had embarrassing moments, but hopefully, we learn from them and can eventually laugh at the memory.

Be prepared to share one of your own embarrassing moments, too, especially a funny one. You can’t expect him to be the only one sharing awkward stories!

8. What was your parents’ relationship like when you were a kid? 

Our parents’ relationship affects our childhood development. But it also affects how we perceive relationships and our worries or fears about falling in love.

This question can lead to deep conversations about intimacy and commitment.

9. What do you do to cope when you get stressed?  

No one wants to be in a relationship with someone who flies off the handle at the merest stressor. But this question also serves to help you recognize some of your boyfriend’s triggers and signs that he is stressed.

10. If you could make a playlist about your teenage life, what songs would it have on it? 

The teenage years weren’t kind to most of us, though hopefully, we have learned to laugh at those memories by now.

This question can spark a funny and meaningful conversation about how he perceived himself during high school.

11. What was the best decision you ever made? 

We all make key decisions that have huge consequences for the rest of our lives. Ask your boyfriend to tell you about a time that he made a decision that turned out to be great — it might even be one that led to him meeting you!

12. What experience taught you an important lesson? 

Whether good or bad, he has had experiences that left a lasting impression on him.

Ask him about a time that he learned something vital from a particular experience, whether it was something small or something that completely upended his life. 

13. What conspiracy theory are you tempted to believe? 

This is one question that might spark a fun and exciting conversation. Even if your boyfriend isn’t the conspiracy type, he might have a theory that seems appealing to him.

It will also give you some insights into how his mind works.

14. What is something you’ve wanted to ask me but been too nervous to say? 

It can be nerve-wracking to ask your significant other some things that are on your mind, so why not open the floor? Give him a chance to talk about things he wants to say.

15. What are some of your family traditions? 

Is your boyfriend from another culture than you? This question is a great way to learn about the traditions that shaped him.

If the two of you are from the same culture, you can still ask about traditions he had growing up to learn more about his family dynamic.

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16. What is one place you never want to go to again? 

Think about the answer to this question, and you probably have a place that immediately comes to mind.

Your boyfriend is bound to have an interesting story about a place he doesn’t want to visit again.

17. What is something that makes you happy? 

Everyone’s answer to this question differs, and the answers can range between big and small.

Regardless, his answer will give you some valuable insight into the kind of person he is (and how you can make him happy when he is feeling down).

18. What is something that makes you cry? 

Unfortunately, we still live in a society where men are discouraged from having authentic emotions. But everyone cries, and his answer might surprise you.

It might be something funny, like a video of a baby animal, or something profound that gives you a glimpse at his compassionate heart.

19. What is a cause that is important to you? 

Everyone stands for something, and if they don’t, that isn’t a good sign. Most of us have issues that are important to us.

He doesn’t have to be actively working on that cause, but he should at least have something that he cares about.

20. If you could move anywhere, where would you go and why? 

It is fun to imagine where you could go and how your life could change if money and responsibilities were not an obstacle. Everyone has their own answer and explanation for why a certain place is meaningful to them. 

21. What was the most challenging choice you ever made? 

Choices are just a part of life, but some are more difficult than others. Most of us can likely remember the hardest choice we ever made because we feel the consequences to this day.

22. What is a place that has been important in your life? 

Maybe he has fond memories of staying at his grandparents’ house or visiting a certain vacation spot with his family.

The answer could be big or small, but it will definitely offer some insight into the important parts of his life.

23. What is your earliest memory? 

Our earliest memories often stick with us because they were formative experiences. We might remember being with someone who has passed away or living in a former home.

These memories are also intimate and private thoughts to share, requiring vulnerability and trust.

24. What can I do to make you feel appreciated? 

Every good significant other wants to make their partner feel loved and appreciated, but not everyone gets that message the same way.

Some people need to be told in words. Others respond to physical affection or their partner doing thoughtful things for them.

25. What was your experience in school like? 

Our school years were some of the most formative of our lives, but they are different for everybody. Was your boyfriend a teacher’s pet who excelled in the classroom?

Was he considered a “problem child”? Was he a social outcast who struggled to make friends?

26. What summer stands out most in your memory? 

Summers are often a transformative time of our lives, particularly during our childhoods.

Whether it is a memory of visiting family during summer break or going on a college trip with a friend, he probably has a life-altering summer experience to share.

27. Have you lost anyone you were close to? 

Most of us have sadly lost people who affected our lives. But you want to know about the people who were important to him, even if they have passed on.

It might give you valuable insight into how he became the man you love.

28. What are you proudest of? 

Give him a chance to brag a little, whether it is about an accomplishment or a difficult decision that he made in the past.

We all have different things that we consider accomplishments, whether they are related to work or our personal life.

29. What are some things that trigger you? 

It’s essential to know about the things that bother your partner to learn about his past and how to help him avoid distress in the present.

It’s not always possible, but it’s a good thing to understand.

30. What was your coming-of-age experience? 

Most of us have a time or event that seemed to signal our coming into adulthood, whether it was a first love or something else.

These can be happy or sad, but they are most of all transformative, making them important to share.

31. What is one thing you have always wanted to do but never had the chance?

Life often holds us back from achieving our dreams. This question asks both what your boyfriend’s dreams are and what has kept him from pursuing them, whether that is real-life responsibilities or opportunities.

32. What is your worst memory? 

This can be a pretty vulnerable question to answer, so be sure not to spring it unexpectedly.

Sharing trauma is an integral part of a relationship, but don’t push it before he is ready to share these intimate and painful experiences.

33. What is something that most men dislike that you love? 

Give him a chance to take a stand when it comes to gender stereotypes. You might also learn something surprising about him.

Maybe he secretly loves doing face masks or watching romantic comedies. You may even find a shared interest that you never knew about. 

34. What is your happiest memory? 

Talking about significant memories can be vulnerable because these are often the things that shape who we are.

His answer will also give you insight into how he became the man he is today and what is most important to him. 

35. What makes you the best version of yourself? 

This question can be tricky to answer, so don’t treat it like a test. It’s more about discovering his ideals, who he looks up to, and who he wants to become in his life.

Tips on How To Ask Your Boyfriend Questions 

There are good and bad ways to ask your boyfriend questions. You shouldn’t be springing intimate questions on him in a public setting or making him feel like it’s some sort of test he needs to pass.

Instead, keep it casual and natural. Here are a few more things to keep in mind:

  • Work questions into conversations naturally
  • Don’t try to force an answer
  • Be open and accepting of his answers
  • Share your own answers if he asks for them
  • Don’t ask too many questions at once
  • Consider the timing of potentially triggering questions

Final Thoughts

Asking your boyfriend questions is a great way to get to know him and understand where your relationship might be going.

But it doesn’t have to be forced — keep it natural, have fun, and enjoy the conversations along the way.