100 Deep Questions To Ask A Guy Before Your Relationship Gets Too Serious

Photo: Unsplash: John Schnobrich
100 Deep Relationship Questions To Ask Your Boyfriend Before Falling In Love & Getting Married
Contributor
Love, Sex

How well do you know each other?

In the first stages of romantic relationships, it's easy to find yourself caught up in the excitement and wonder of falling in love. It may also feel awkward or intrusive to keep asking a guy you're dating questions, even if you know it's an important thing for you to do.

But the truth remains that before you can even begin thinking about making a commitment to someone, let alone consider getting engaged or married to them, there several deeply important questions to ask your boyfriend in order to make an informed judgment call about your compatibility and chances for success in a relationship over the long haul.

Of course, your earliest conversations with someone new should be about creating sparks between the two of you, not some boring trade back and forth of personal information.

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

To help you out, I've gathered these suggestions for you to review in order to determine what you believe is most critical for you to ask your boyfriend.

Here are 100 deep questions to ask a guy (or a partner of any gender) at various stages of your relationship — and definitely before you fall in love or even consider getting engaged or married.

During the earliest stages of dating:

1. How long have you lived in the city/(town)/(area)?

2. Are you single? Divorced? Widowed?

3. Where do you work?

4. Do you belong to any single's clubs?

5. What do you like most about women?

6. How important are good looks to you?

7. What's your idea of an attractive woman?

8. Are you interested in companionship and/or a long-term relationship?

9. Do you like to read? If so, what do you read?

10. How often do you go out and have fun?

11. Are you active in any sports?

12. What are your interests?

13. How often do you do these things?

14. Which do you like best?

15. Do you like to travel, and if so, when and to where?

16. What kind of vacations do you like?

17. What kind of vacation would you take with a partner?

18. Describe your ideal roommate.

19. Are you involved in civic, community or work-related organizations?

20. What is your education?

21. Are health and nutrition important to you?

22. How do you stay healthy?

23. Do you like children?

24. Do you have children? How many? How old are they?

25. Do you spend much time with them?

26. Do you like animals? Do you have any pets now?

27. What are your feelings about religion and church?

28. Are you employed? How long have you been at your job?

29. What kind of work do you do?

30. Does your work require a lot of your free time?

31. What do you do when you want to relax?

32. What is your favorite hobby or leisure time activity?

33. What kinds of things do you like to do with someone else?

34. What kinds of things do you do with your free time?

35. What kind of music do you like?

36. Do you follow any spectator sports? Which one(s)?

37. How do you keep up with current events?

38. What are your friendships like?

39. What do you do with your friends?

40. How would your friends describe you?

41. What were your friendships like when you were growing up?

42. Is a sense of humor important to you?

43. How do you structure your weekends?

44. Do you smoke?

45. Are you a social drinker?

RELATED: 3 Questions To Ask A Guy To Make Him Feel Deeply Attached To You

Unless you fall in love at first sight, you should save the questions about other areas of his life that might be a bit touchier for later.

Some questions require more trust and frankness than others, and should be saved for a time when you're both feeling more established in your relationship.

Here is a list of riskier questions to ask once when you're interested enough to start getting down to the nitty-gritty:

46. Do you own a home?

47. What abilities are important to you in a partner?

48. Do you consider yourself to be sensitive and caring?

49. Are you a perfectionist? An athlete? An intellectual? A workaholic?

50. Do you feel happy most of the time?

51. Do you have a good/working relationship with ex-partner?

52. How do you feel about divorce?

53. What's the feeling you most often experience when things go wrong? What do you do?

54. What do you want from others when things go wrong?

55. What do you like to talk about?

56. What conversations do you avoid?

57. What do you regard as your biggest personality strength?

58. What is your biggest personality weakness?

59. What emotions do you have trouble controlling?

60. What aspects of a relationship do you enjoy?

61. What aspects of a relationship are difficult for you?

62. What shortcomings would you need to work on in a relationship?

63. What was your worst failure in life?

64. With what do you feel is your greatest need for help?

65. What was the greatest turning point in your life?

RELATED: 20 Deep Questions To Ask Your Guy (So You Can Fall In Love With Each Other All Over Again)

When you like him well enough that you are thinking about a possible commitment, it's time to delve further and find out if his lifestyle, values, and priorities match your own.

Here are more in-depth, personal questions to ask when you believe you might be ready to commit to a long-term relationship:

66. How do you like to make decisions?

67. Do you make decisions differently when someone else is involved?

68. Do you have trouble sharing your feelings with others?

69. Do you speak up about your opinions and convictions?

70. How do you solve problems?

71. What are your career goals?

72. Are you able to set goals and achieve them?

73. Do you like your mother/father?

74. What were your parents like when you were growing up?

75. What are your parents like today?

76. Do you get along with your parents?

77. How did your parents influence your opinions about marriage?

78. What advice have your parents given you about child-rearing?

79. Are you financially secure?

80. How do you feel about borrowing money?

81. Do you pay your bills on time?

82. What is your attitude toward material possessions?

83. Do you follow your own direction or do you tend to take other people's advice?

84. How do you feel about arguments?

85. How did your parents handle disagreements?

86. Has your parent's marriage influenced how you feel about relationships?

87. Are you as sociable as you want to be?

88. Do you hesitate to try new things?

89. Do things usually turn out the way you want them to?

90. Is there an area in yourself or your life that you would like to change?

91. Do you feel you are in control of your life?

92. Do you know where you are going in life?

93. Are you getting what you want out of life?

94. Have you ever had a drinking problem?

95. Have you ever had a drug problem?

96. Have you ever been arrested?

RELATED: 8 Questions To Ask Yourself If You Want True Love That Lasts Forever

And finally, here are specific questions to ask at whichever moment in the relationship you are first contemplating having sex for the first time:

Note: Do not be intimidated into letting these questions go unasked. Your life and your health are your utmost concern.

97. Are you comfortable talking about sex?

98. Are you comfortable using condoms and/or other forms of protection?

99. Have you ever been with someone who tested positive for HIV?

100. Have you ever been tested and/or treated for STIs?

Getting to know someone under any circumstances can be challenging, but there are facets that make up a person's identity that you need know before judging your compatibility with them.

In general, you must know someone well before you can make an informed decision about committing to a relationship, although several women I interviewed told me the first time they went out with their future husband they knew he was the one. It can happen, and it does, but better safe than sorry.

And now, it's time for romance!

RELATED: 18 Signs You're Falling Into Genuine True Love With Your Soulmate

Susan Bratton is a trusted sex advisor to millions and is dedicated to helping others discover how to give and receive feedback in the bedroom without feeling criticized.

*These questions originally appeared in a book written by the author's mother, "Time for Romance: A Woman's Guide To Energizing Your Love Life."

This article was originally published at Personal Life Media. Reprinted with permission from the author.

Author
Contributor