40 Questions To Ask A Guy If You Want To Know If He’s For Real


In a world of fakes, it can be hard to know who is “for real” or not. While I might not rattle off this entire list on a first date, these are some questions that have helped me determine whether a man I was interested in had compassion, love, depth, and self-reflection.

1. What’s something you’ve learned at your job / school?

2. What’s something you regret?

3. Where do you see yourself in a year?

4. What about in five?

5. What’s your biggest goal right now?

6. What things do you value in a friend?

7. What about in a significant other?

8. What’s one important thing you learned from your mother?

9. What kind of relationship do you have with your mom?

10. What is something you hope to learn in the next year?

11. What is one time that you’ve made a mistake?

12. Where’s somewhere you’d like to travel?

13. And why?

14. What is something they look for in a significant other?

15. What are the deal breakers in their relationships?

16. What’s a quality they really admire in someone else?

17. Who is a public figure that you really admire?

18. Why?

19. What does “family” meant to you?

20. Do you have a best friend?

21. How did they become your best friend?

22. What is a political issue that you care about?

23. What is your opinion on the current election?

24. If you could live anywhere in the world, where would it be?

25. What is the accomplishment you are most proud of?

26. What does a long term relationship look like to you?

27. What are you looking for right now?

28. What do you think commitment looks like?

29. What’s one thing you’ve learned from a past relationship?

30. What are the best times to talk to you?

31. How do you best communicate? (text, phone, in-person)

32. How do you resolve problems?

33. What would your friends say your best quality is?

34. Do you believe in “love”?

35. Have you been in love? How many times?

36. What’s your favorite non-physical attribute about yourself?

37. What’s your favorite non-physical attribute in other people?

38. What’s a time that you were really proud of yourself?

39. How do you best support your friends and family?

40. What do you think the most important quality is to relationships that last? TC mark

Brittany Cox

Ontario real estate specialist. I write relationship advice, #GuysInsight, sex, and snark.

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