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20 Deep Questions to Ask Boyfriend

These deep questions aren’t for the faint of relationships. Getting to a deep level with your boyfriend is as important as being light hearted and fun when the situation calls for it. Asking these conversation-evoking questions, shows you care about your SO in a way only serious girlfriends do. He may not feel comfortable answering some of these questions, and prepare yourself for him to repeat the question back to you.

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11 What do you most regret?

While all of these questions have potential to show your man’s true colors, this one for sure will. If he answers. Regret is a powerful thing that can drag even the most powerful men down. If he answers with a strong regret, this could be the perfect opportunity for you to support him.

1. What do you most regret?

22 What was the happiest moment in your life?

He will likely answer this one with out hesitation. Knowing what makes your man happy could come in handy down the road too. This could be surprising as well.

2. What was the happiest moment in your life?

33 Do you believe in God?

This question could possibly have come up before if you have been together for a long time. However, if you have not talked about this yet, it is important to for the relationship, but can also be a very interesting and deep conversation.

3. Do you believe in God?

44 Has something significant happened that changed your life?

Using the word “significant” I mean something special, not a big grand gesture or event. It could even be someone of respect telling him something wise in his time of need.

4. Has something significant happened that changed your life?

55 Do you believe in ghosts?

This could be a very interestingly deep conversation if he replies yes! Tell him you want to hear the story of why he believes. Or ask him if he would go to Alcatraz or somewhere really haunted!

5. Do you believe in ghosts?

66 What are you most scared of?

He could say ghosts after that last question! But, it is always interesting to hear what people are most scared of. It could range from a number of things.

6. What are you most scared of?

77 What do you think your spirit animal is and why?

Be sure to maintain a conversation with this fun question. Talk about why you agree or why you disagree. What you think your sprit animal is and are your animals compatible with each other? This question has the potential to grow into an amazingly deep conversation!

7. What do you think your spirit animal is and why?

88 If you could change one thing about yourself, what would it be?

This is could be a difficult question for him to answer, or he may be insecure about the thing he wants to change. Be sure to be supportive if that is the case. He could also reply with a number of things not quite as serious that you could help him change.

8. If you could change one thing about yourself, what would it...

99 What is something you are afraid to tell people?

He may ask to pass on this question and don’t press him to answer. When he feels comfortable confiding in you, he will!

9. What is something you are afraid to tell people?

1010 If you could talk to one dead person who would it be?

This could be a very personal question if a very close friend or relative has passed away. If he doesn’t have a personal experience to apply, this could also be a very interesting conversation. He may reply with a famous founding father, Albert Einstein, or the person who invented beer. It all just depends on his personality?

10. If you could talk to one dead person who would it be?

1111 How is your relationship with your parents?

This opens the door for him to talk about a lot of things. It seems that very few people don’t have issues with their parents. Listen when he answers this question.

11. How is your relationship with your parents?

1212 Do you have any bad habits?

Smoking, dipping, drinking. It could be a range of things as well. If he is willing to let you help him break his habits, help him.

12. Do you have any bad habits?

1313 What is your goal in life?

This is a great question to ask in any relationship. Knowing exactly what you want in life could take years to figure out, but talking about it now can help you keep your priorities straight. This could easily turn into a long talk as well.

13. What is your goal in life?

1414 What do you think will bring the end of the world?

Typically he will answer a plague or a war. It will be an interesting conversation to talk about what he thinks the details will be. This may even lead to a conversation about politics or advances in medical technology.

14. What do you think will bring the end of the world?

1515 If you could have three wishes what would they be?

Hopefully the previous chain of thoughtful questions will have him in the right mind set when you get to this one. Try to urge him toward 3 thoughtful wishes instead of a Ferrari, a million dollars, or his own island.

15. If you could have three wishes what would they be?

1616 Would you want to know the exact date and time of your death?

This could become a fun debate for the two of you if you have opposing views. My boyfriend and I happily agreed not to know, but then also talked about why. It was a good conversation.

16. Would you want to know the exact date and time of your deat...

1717 If money wasn’t a factor what would you want do as a career?

Knowing what he would really like to do with his life can be an interesting topic as well. Maybe you would have similar answers, which would be a nice thing to dream about together.

17. If money wasn’t a factor what would you want do as a career...

1818 If you had a secret serum that made someone tell the truth, who would you use it on and what would you ask?

This is just a flat out fun question that also has the ability to turn into something serious. Would you ask JK Rowling a question about one of the holes left in the Harry Potter series, or would he ask someone close to him a personal answer. This question will simply go where ever your boyfriend wants it to.

18. If you had a secret serum that made someone tell the truth,...

1919 What moment were you most proud of yourself?

If he is a shy guy this may take some prying to get out of him. You may have to push him a little, but for this question that is okay!

19. What moment were you most proud of yourself?

2020 What do you feel you could do better in your life?

Again, this is a question that gives you the opportunity to help your boyfriend improve his lifestyle. Maybe tell him what you think you could do better in life too and work on it together.

20. What do you feel you could do better in your life?
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