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100 Questions To Ask On A Date

If you’re dating, these questions could be a good refresher before you meet someone new:

These questions are just suggestions to help you know what questions to ask.


Early conversations should be about creating sparks between the two of you – not about trading boring information. So here is a sampling of some casual, conversational questions to get you started:

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 clubs?
5. What do you like most about women?
6. How important are good looks to you?
7. Describe your idea of a good-looking woman.
8. Are you interested in companionship, and/or a long-term relationship?
9. Do you like to read? 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? When and 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. Is 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?

Unless you fall in love at first sight, you should save getting down to the nitty-gritty, such as finding out his attitudes toward other areas of his life that are a little touchier. Some questions are a little riskier, require more trust or frankness than others, and should be saved later in your relationship.

Riskier questions to ask later 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. Have you ever been in a divorce recovery program?
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 chief personality strength?
58. What is your chief personality fault?
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 life?

When you like him well enough, and you are thinking about a possible commitment, you need to know if his lifestyle, values and priorities match yours. For example, how does he handle money, relate to his parents, what are his relaxation activities, what are his attitudes about housework, decision-making, problem-solving and sex?

In-depth personal questions to ask later when you are 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. How 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 childrearing?
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 in jail?

More personal questions to ask later when you are contemplating sex. DO NOT be intimidated. Your life and your health is your utmost concern:

97. Are you comfortable talking about sex?
98. Do you object to using condoms during sex?
99. Have you ever slept with someone who tested positive for HIV?
100. Have you ever been treated for a venereal disease?

NOTE: Here is my “Safe Sex Conversation” fully updated for you to use to be very careful when sleeping with a new lover.

Getting to know someone can be a challenge. There are different facets of a person you should know before you can judge your compatibility. Generally, you must know a person 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 to the lucky ones.

These questions come from my mother’s book,

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If you want to discover whether or not a person is soulmate material, you’ll want to check out my dating videos on BetterLover, my Relationship Magic book, and the Sexual Soulmate Pact. 

Click Here To Download The Sexual Soulmate Pact ⇐ 2-Word Phrase That Ignites Passionate Lovemaking

Dating Videos On BetterLover ⇐ Check Out My Videos To Help You Meet A Loving Partner

Check Our Relationship Magic ⇐ The 1 Magic Question Safeguards Your Relationship 

Let me know how you like the questions!

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