20 Deep Questions to Ask Your Boyfriend

By on January 4, 2014

Knowing the basics about someone is great. But diving deep into the crevices of one’s brain and finding out the answers to life’s deepest questions is even better. Try asking your boyfriend one of these 20 deep questions to ask your man and find out what’s truly going on in the depths of his mind.

1. Do you think there is an afterlife?


Everyone has an entirely different idea when it comes to the afterlife, from an extravagant magical place to a empty void. The best part about this question is there is no right or wrong answer- in fact, nobody knows the answer period. See how wild and imaginative your man may be about what’s to come.

2. How much money would you donate to charity? Which charity?


With this question you can identify your man’s real passion. Would he be willing to spend his entire paycheck on the charity of abused animals, or is would he rather spare some money for the homeless?

3. What’s your biggest regret in life?


We have certainly all made mistakes in life, but what does your man regret the most? With this question you can really find out how ‘bad’ your guy was in the past and see if he truly has remorse for something terrible he has done. This could also make for a very funny story!

4. What is one thing you would change about yourself?


Nobody loves themselves completely. But how insecure is your guy? Would he change something basic, like his eye color, or would he want to change himself from being selfish about the things he has to being more giving to others?

5. What era would you visit if time machines existed?


This question can give you some great insight on where your man’s head is. After all, some of us simply want to travel to the 80’s for the crazy hair and exciting music while others want to go back to ancient times to discover their hidden secrets within the caves.

6. If a genie granted you 3 wishes (and you can’t wish for additional wishes), what would you wish for?


See if your boyfriend would wish for a beautiful ritzy house or lavish vehicle or if he’d spend his own wishes on helping others.

7. How do you define yourself?


As everyone defines themselves in different way, whether it’s their social status, amount of money, or the way they act around others, and finding out what your boyfriend thinks can uncover a lot about his personality.

8. What would you do if you were told you only had 1 month to live?


A single month is surely not a lot of time. You’ll find out his priorities with this simple question.

9. How would you feel if you were told you terminally ill?

Nobody wants to even think about this terrible event, but how would your boyfriend react? Would he keep a smile on his face and hide it from you, or become a wreck in your arms?

10. What is the worst dream you’ve ever had?


Dreams can be incredibly creepy, and may even appear real. Find out what once haunted your man in his slumber.

11. What defines beauty?


Don’t let his answer be cut off with ‘you’. Although this is an incredibly sweet comment that will melt you, keep prying for what your man truly thinks is beautiful and what defines the word itself.

12. What brings true happiness?


Some people believe happiness can be bought, while others believe happiness comes from being around the ones you love. Find out what your man thinks about this whole debate.

13. What would you do if your family unexpectedly died in a horrible car crash?


Surely this is a thought that sends shivers down your spine, but it’s a prying question to find out how he would handle such devastation.

14. What is something you are deeply offended by?

Everyone has their own set of beliefs and their own comfort zone. What ticks off your man? What does he find absolutely grotesque that others are completely OK with?

15. What part about the future scares you?


With so many advancements continuously popping up, it’s hard not to be scared of what’s coming. Find out what your guy is most afraid of and why!

16. Would you rather be respected or liked?

Such an intense question, as sometimes you simply can’t have both. Find out whether your man would rather be a likable character doing the wrong thing for attention or a respectable man who sticks to his guns.

17. If you had to pick a new name, what would you choose?


Maybe he’d go with something really basic, or maybe he’d come up with a funky name you’ve never heard before. This could get interesting!

18. What would be your last meal?


He has absolutely no more chances to eat. Will your guy go for a lavish meal with steaks and lobster or simply have a feast of desserts and sweet treats?

19. What do you think about when you’re by yourself?

With this question you will find out whether your man is a philosophical guy who wonders about the world or if he simply thinks about what he will have for dinner that night.

20. If your house was on fire, what would you go back to save?

on fire

Again, this question allows you to uncover what your man sees as important. Would he go back to save his beloved pet, leaving everything else to burn, or would he snatch up his expensive video game equipment?


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