20 Questions To Ask Your Guy When You REALLY Want To Know Everything

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Let’s face it – your guy is pretty amazing; but, he also doesn’t like to talk about himself. Why is that? Maybe it’s his selfless attitude, or he’s just a private person. Guys aren’t usually the masters of talking. Either way, you’re lucky to have him in your life.

When you’re dating or even if you’re in a committed relationship, there is nothing you want more than to learn everything there is to know about that special guy. But trying to get him to open up is sometimes like cracking a safe. Good luck learning that lock combo.

But you really want to know. What are his deepest fears? What does he want most in this world? If you could just tap into his brain for a day, what secrets could you unlock about him? And knowing him on a deeper level would help you feel even more connected – As a married couple or as partners, there is nothing better.

That’s why we’ve come up with a list of 20 questions to ask your guy to learn more about him, and love him more in the process. These are questions that really get into what he is all about as a person, inside and out.

The problem may be actually getting him to answer these questions. Maybe agree to get him to answer one a day via text, if you also answer the question, too. Or make it a game – once he completes all 20 then you’ll give him a special surprise. It could also be fun to have each of you answer these questions about HIM… and then compare your answers. This may take some convincing, so make it fun and hopefully he’ll see the value in doing it.

So print these questions, text them, or email them – just get them to him so he can answer them. You could even start with the less invasive questions at first to get him warmed up. Have fun!


Here are our 20 questions to ask your guy:

1. Are you an introvert or an extrovert? Why do you think so?

2. Who is your hero or the person you look up to most (dead or alive)?

3. What is the biggest thing you look for in a guy friend? A girl friend? A marriage partner?

4. What is one of your strengths (physical, mental, spiritual, etc)?

5. What is one of your weaknesses (physical, mental, spiritual, etc)?

6. If you could travel anywhere right now for free, where would you go?

7. What is your dream job? Has this always been your dream job or has that changed?

8. If you could fix one thing in the world by just wishing it to change, what would it be?

9. What are your top three favorite foods (meals, snacks, desserts)?

10. What is your most embarrassing moment?

guy at rest

11. If someone were to portray you in a movie about your life, which actor would it be?

12. What is one thing you have always wanted to do?

13. What is your biggest fear (real or imagined)?

14. What motivates you the most in life?

15. If you had a free day to yourself, what would you do?

16. Have you ever lost a loved one, and what did it feel like?

17. What is your favorite book of all time?

18. What three things would you bring with you to a deserted island?

19. What do you think other people think about you when they first meet you?

20. When/how do you feel most loved?

Be sure to write down his answers so that you will both remember them in a year or two. His answers are bound to change over time, so if you revisit these in the future it would be fun to see if anything has changed.

Did I miss any important ones? Tell me about them in the comments below!

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  1. Great list of questions to ask! Thanks for sharing at #HomeMattersParty hope to see you back!

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