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38 Deep Questions To Ask Your Boyfriend You’ll Ever Need

38 Deep Questions To Ask Your Boyfriend You’ll Ever Need

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If you’ve been in a relationship for a while, you might be looking for deep questions to ask your boyfriend so that you can get to know him better. Or you might want to ask him about your relationship so that you can feel like you’re on the same page. Whatever your reason for wanting to ask deep questions, the list below should be your starting point.

This list of questions to ask your boyfriend is incredibly useful to help encourage your boyfriend to open up a little – to share his thoughts, feelings and experiences. Deep questions to ask your boyfriend can help you to feel like you have a better connection with each other. Not only will you feel closer, but you’ll feel like you understand him a little better.

So browse through the list and take your pick from the interesting, fun and personal questions to ask your boyfriend below. Note a few down and have them ready to drop into a conversation, wherever they feel natural.

Contents

9 Best deep questions to ask your boyfriend

If you’re looking for the top questions to help you find out more about your boyfriend, look no further. These are the questions you need to know and need to ask if you’re hoping to deepen the connection between the two of you. Remember to have an answer ready in case your boyfriend asks the question back to you so you can keep the conversation flowing.

Here are the 9 best deep questions to ask your boyfriend:

1. If you woke up tomorrow with no fear, what would you do first?

A great question to find out more about your boyfriend’s aspirations.

2. What is one behavior that you never tolerate?

It can be really useful to learn about what someone likes and dislikes in other people.

3. What’s one thing you think makes our relationship unique from everyone else’s?

You’ll be pleased with whatever answer he gives when you ask him this.

4. What secret haven’t you told me yet?

Want to find out something brand new about your boyfriend? This is the question to ask.

5. When did you last sing to yourself? To someone else?

This is fun both to ask and to answer.

6. How do you best connect with others?

Not only will you learn more about your other half, but you’ll also be able to put the information into practice.

7. What’s your favorite family tradition?

This is one of the best deep questions if you’re hoping to learn more about his family.

8. What are your religious views

Asking about religion is important in a relationship so this is a good query if you haven’t been together long.

9. How do you feel about my family

Make sure you’re ready for an honest answer if you ask this question.

10 Questions to ask your boyfriend to get to know him better

Questions to ask a guy to get to know him better can offer some really interesting insights into someone’s personality. They let your boyfriend feel like he can open up to you and provide a little look into his past, present and future. If you’re hoping to find out more about your boyfriend, these questions to ask your boyfriend will be insanely helpful. They work best as part of a conversation rather than out of the blue, so be sure to drop a couple in when you’re talking about a relevant topic.

Here are 10 deep questions to ask your boyfriend to get to know him better:

10. What makes you insecure?

This might be difficult for him to answer, but you’ll find out a lot more about his personality with this question.

11. Do you want children?

An important question for every girlfriend to ask their boyfriend.

12. What do you wake up excited about?

This is a lovely question to ask your partner and one that will offer an interesting answer.

13. How often do you see your family?

If his family lives far away, this is a great way to get him talking about them.

14. What’s the best way to earn somebody’s respect?

There’s no doubt that this topic will get him thinking.

15. Which fictional character would you marry if you had the chance?

Although you might not like to think of him marrying someone else, he’ll have the chance to tell you about a character, movie or book that he really likes.

16. Do you ask permission or ask for forgiveness?

If you’re still learning more about your boyfriend and his personality, this deep question will help you find out what kind of person he is.

17. What is the most important political issue to you?

Politics can be tricky to talk about as a couple but it can be helpful to find out about his views early in the relationship.

18. What’s been your favorite age so far and why?

If you’d like to learn about his past or childhood, this is an easy way to discover more.

19. Who inspires you regularly?

Find out about the person that he looks up to when you ask your boyfriend this interesting question.

11 Deep but fun questions to ask your boyfriend

Deep questions to ask your boyfriend can be challenging and can force him to think hard, so why not lighten the mood? Throwing in a few of these fun questions to ask your boyfriend will encourage him to answer honestly without giving too him of himself away. These are questions that you can throw into a conversation or ask out of the blue and he’ll really enjoy thinking of the answers.

Here are 11 deep but fun questions to ask your boyfriend:

20. Where is the craziest place you have danced?

Even if your boyfriend isn’t much of a dancer, he’ll have a fun answer to this question.

21. What’s your favorite waste of time?

Find out a bit more about what your boyfriend thinks are good and bad ways to spend his time.

22. If you could learn a new skill instantly what would it be?

You’ll quickly find out what he regrets not learning, or what he hopes to learn to do in the future.

23. What did you learn a little too late?

This is one of the deep questions that will really make him think hard.

24. If money was no object, where would you live?

He might have a quick answer to this – many of us have pondered over where we’d live if we won the lottery.

25. What is something you probably should do, but will never do?

This is an interesting and thought-provoking topic to discuss.

26. What terrible movie do you love?

A very fun question – be sure to have an answer for your favorite terrible movie too.

27. If you have a logo instead of a name, what would it look like?

It’s likely that your boyfriend will never have been asked this question before.

28. What’s your favorite way to receive affection?

This is very useful to talk about in a relationship and his answer might surprise you.

29. If you could change one thing in history, what would it be?

Even guys who didn’t pay attention in history class will be able to come up with an answer.

30. What is the weirdest thing that’s happened to you in bed?

This is certainly a fun question to ask if you want to find out more about your boyfriend’s experiences.

8 Deep but interesting questions to ask your boyfriend

The best kind of questions to ask your boyfriend are interesting questions. These will make him think about his answer for a moment before offering it to you. Interesting questions to ask a guy are amazingly useful because they not only tell you more about him but also more about how he sees the world. It’s always awesome to feel like you understand your boyfriend a little better, right?

Here are 8 deep but interesting questions to ask your boyfriend:

31. What always makes you smile?

You’ll definitely find the reply interesting when you ask this question.

32. What is the best part about being in a relationship?

Even the toughest of guys will soften up when they ponder an answer to this topic.

33. What is the most worthwhile goal a person can dedicate their life to?

If you want to make your boyfriend think hard, this is a great question to ask.

34. Why do people do things that they know hurt themselves and those around them?

This one of the deepest and most interesting subjects to talk about.

35. What, according to you, is a perfect life?

A lovely question to ask if you’re hoping to find out more about a guy’s aspirations.

36. What do you expect from a loving relationship?

This helps a guy to open up about past relationships and think about what they hope the future will hold.

37. What are some things in your childhood you’d like to improve upon for your child/children?

Want to find out more about his childhood? Ask him this and he’ll tell you everything you need to know.

38. If you could be anyone else for a day, who would you choose?

If you think you already know about his idols, you might be surprised when you hear your boyfriend talk about who he’d love to be for a day.

How to Pick the best deep questions to ask your boyfriend

This list of deep questions to ask a guy is really valuable for learning more about your boyfriend. But how do you choose the best questions? Just follow the steps below and you’ll quickly find out which questions he’ll respond to the best.

Here is how to pick the best deep questions to ask your boyfriend:

1. Does he like talking about the past or future?

Think about whether your boyfriend prefers to talk about the past or future and you’ll know which questions he’s most likely to enjoy answering. If he likes to talk about the past, questions about his experiences or childhood are a great bet. If he prefers to talk about the future, he might like answering questions about his aspirations or plans.

2. Does he like serious or fun topics?

Asking about fun topics is usually a good choice – who doesn’t like to answer fun questions or think of fun scenarios? However, some guys are also happy to talk about serious subjects too. If he often speaks seriously, he might respond really well to deeper questions about his views on more thought-provoking topics.

3. Does he enjoy talking about love and relationships?

Some guys like to talk about relationships, while others shy away from the subject. Although you might be desperate to ask him about love, he might not be happy to open up about this yet. In this case, it can be a great idea to choose questions about his past or his family – from his answers, you can begin to understand his take on relationships a little better.

Downloadable List of Deep Questions To Ask Your Boyfriend

Here is a downloadable list of deep questions to ask your boyfriend (right click the image and select Save Image As…):

More Awesome Tips to Talk to Guys

Asking deep questions can be a great way to get guys talking, but there are other ways you can get to know him. If you’re looking for tips to help you have great conversations with your boyfriend or a guy you’re hoping to date, you’ll find loads of inspiration below:

  1. These flirty questions to ask a guy are perfect to help you flirt with a guy you’ve just started dating or one that you’ve been chatting to for a while.
  2. Want to find out more about a guy? These personal questions to ask a guy are just what you need when you’re hoping to get to know him better.
  3. Random questions to ask a guy can be really useful for pauses in the conversation or to spark up a conversation with a guy you’d like to speak to.

In Conclusion

There’s no better way to get to know a guy than by using these deep questions to ask your boyfriend. Throw a couple into your next conversation and you’ll get to learn more about his past, his personal views and his plans for the future. Be sure to note down your favorites and you’ll never be stuck for an awesome question to ask.

About The Author

Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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