36 Deep Questions To Ask Your Guy To Get To Know The Real Him

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36 Deep Questions To Ask Your Guy To Get To Know The Real Him

These are fun, thought-provoking questions I’ve taken from Mandy Len Catron’s Modern Love Essay, Arthur Aron from Sage Journals, Thought Catalog, Stronger Marriages, Quora, and Reddit, and reworded. It’s questions that you and your partner/date can ask each other.

Depending on the interaction, this may take an hour to a whole night. But within that time, you’ll feel a whole cloud of emotions: surprised, amazed, speechless, maybe even a bit embarrassed, but ultimately more in love than ever.

Personally, I’m sick of dates asking me the same superficial questions over and over again — questions that barely scratch the surface towards knowing the real me. I don’t blame them though. They’re just trying to fill the awkward silence with something interesting to say.

RELATED: 7 Deep Questions To Ask Your Guy That'll Make Him Fall Even More In Love With You

Luckily, I’ve scoured through tons of articles offering some refreshing date questions to ask a guy and, through my own filtering process, I’ve personally picked the best ones that will bring that special someone even closer to you.

1. If you woke up tomorrow with no fear, what would you do first? (Source: Reddit)

2. If you can choose anyone in the world, who would you want as a roommate? (Source: NY Times)

3. You’re about to go head-to-head with 100 people in front of a live audience.The prize is $1 million if you can do one single thing better than every person there. What is your talent? (Source: Reddit)

4. What would you want to be famous for? (Source: NY Times)

5. What have you dreamed of doing for a long time? Is there something holding you back? (Source: NY Times)

6. If you had an extra $1,000 to spend, what would you get? (Source: Reddit)

7. If you could live up to 100 years old and possess either the mind or body of a 25-year-old for the last 75 years of your life, which would you choose? (Source: NY Times)

8. Does spending time with other people energize you or drain you? (Source: Quora)

9. If money keeps rolling into your bank but you still had to work, what job would you choose to do? (Source: Quora)

10. What’s better, doing the right thing or doing things right? (Source: Quora)

11. If you were the ruler of the world, what’s the first law you would make? (Source: Stronger Marriages)

12. If there’s one thing you could change about how you grew up, what would it be? (Source: NY Times)

13. What is one behavior you can never tolerate? (Source: Quora)

14. When’s the last time you cried in front of another person? By yourself? (Source: Reddit)

15. What would be the “perfect” day for you? (Source: NY Times)

RELATED: 50 Questions To Ask Your Boyfriend Or Girlfriend (Before Your Relationship Gets Too Serious)

16. What quality do you value most in friends? (Source: NY Times)

17. If a psychic knew everything about your life, your future, and who you are, what would you ask him/her? (Source: NY Times)

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18. What do you feel most grateful for in your life? (Source: Quora)

19. What’s the biggest thing you’re trying to accomplish this year? (Source: Reddit)

20. If you could wake up tomorrow with a new quality or ability, what would it be? (Source: Reddit)

21. What is something you never want to do again? (Source: Reddit)

22. How close do you feel with your family? Do you think you had a happier childhood than most people’s? (Source: NY Times)

23. What would you do tomorrow if you lost your job and money and had to start over? (Source: Quora)

24. What’s the proudest moment of your life? (Source: NY Times)

25. What’s the best-treasured memory you have? (Source: NY Times)

26. What’s the most disturbing thing you remember? (Source: NY Times)

27. If in one year you were to suddenly die, what would you change about the way you’re living now? And why? (Source: Quora)

28. What’s too serious to be joked about? (Source: NY Times)

29. If one of your family members was chosen to die, whose death would disturb you most? Why? (Source: NY Times)

30. Share 5 positive characteristics your partner has. (Source: NY Times)

31. Have you ever rehearsed what you wanted to say to someone? When and why? (Source: NY Times)

32. Be honest and tell your partner what you like most about them. It should be things you don’t say on the first meet-up with someone. (Source: NY Times)

33. If you were to die by the end of today without a chance to talk to anyone, what would you most regret not saying? (Source: NY Times)

34. Your house catches fire. After running in to save your loved ones and pets, you have time for one final dash to save one item. What is it and why? (Source: Reddit)

35. Is there anything you consider absolutely unforgivable? (Source: Quora)

36. Tell your partner a personal problem and ask how he or she would do to fix it. Then ask your partner to reflect how you feel about your problem. (Source: NY Times)

RELATED: 5 Deep Questions To Ask A Guy That'll Make Him Fall For You

Tiffany Sun is fighting to rebuild her life by doing the things she never dreamed of doing. Now in Southeast Asia, writing her journey. Check out her website, and follow her on TwitterFacebook, and Instagram.

This article was originally published at Medium. Reprinted with permission from the author.