Top 100 Questions to Ask Your Potential Boyfriend/Girlfriend

Dating is all about having fun, but at some point if you do find yourself with someone that you are thinking of maybe having something a little more long term; there are certain topics you should cover. You will save yourself and them a lot of everything if you talk about these things at some point. Again, when that point is will depend on you and what you think the other person is ready to respond to. You may consider making a list and have them answer the ones they are able to answer. It is interesting also, maybe, the questions they can’t or don‘t want to answer. I think this would be a fun exercise either way! :D I pulled a list off the net and modified all of the questions; dropped a few and added some. In no particular order:

Okay, I’ve read the list EVERYONE should read it and answer these questions, at least for yourself. Give your life a little more clarity. Fathers, definitely have any guy wanting to date your daughter answer these questions, in writing, signed and dated! :D

Wow. I just revised this 3/15/14 :D If someone refered you to this, tell them to check back. The questions are much better. I will take suggestions too, remove, add, revise :D

Also blog topics. I am always looking for suggestions. Please :D

1. What do you see yourself doing with your life in 5 years, 10 years?
2. Have you had an experience you would say has impacted the direction of your life?
3. Have you had to make an important decision that affected the direction of your life?
4. Are there people you don’t like? Are there people that don’t like you?
5. Where do you consider good places for a couple to be romantic?
6. What has been an embarrassing moment for you?
7. Are you ever bored?
8. What are good leisure activities a family should try to do together?
9. Are you okay that I still might have some feelings for my Ex?
10. What is your definition of emotional intimacy?
11. What do you think of this expression: Where there was fire, ashes remain.
12. What sort of future financial plans/goals do you have?
13. What is your biggest goal in life?
14. What is your favorite book/author?
15. Describe yourself in 3 words.
16. Tell me your 3 weaknesses.
17. Who is your hero, do you have more than one?
18. What are the most important things in life?
19. What questions would you like me to answer?
20. What are your bad/good habits?
21. What are your point of view of the world? Liberal/conservative, spiritual/atheist
22. What would you do to leave an impression on a person on your first date?
23. What to you would the perfect life consist of?
24. Is there an age where being a virgin, you think, would be awkward?
25. What’s been your most intimate experience? What it emotional as well as physically intimate?
26. Can you have emotional intimacy without physical intimacy?
27. Do you still have feelings for an ex?
28. How long did your most intimate relationship last?
29. Do you regret any of those intimate experiences with that person?
30. Have you ever had the feeling you were being watched, in general, not during, you know.
31. What was your most conflicted emotional moment?
32. Do you usually follow your heart or your head?
33. What is your opinion about same gender relationships?
34. Do you think the past matters in a relationship?
35. How would you react if I told I have had a relationship with a partner of the same gender?
36. Do you believe in any god or gods? Why? Are you spiritual?
37. Do you have any opinions about politics?
38. Do you have any hobbies?
39. Have you ever experimented with legal/illegal drugs?
40. What do you think is the key to good parenting?
41. Do you like pets in the house? Do you like pets?
42. What is the weirdest thing about you to most people?
43. Tell me something about your first kiss.
44. If your parents don’t like me for some reason, is that a deal breaker?
45. Have you ever had a one night stand? If you did, do you regret it?
46. Do you believe in soul mates?
47. Do you have a criminal record, any contraction of diseases?
48. What is your dream job?
49. Are you willing to stay away from your family if you ever have to for a job?
50. Which living celebrity/author/singer would you like to know?
51. If you could meet a famous dead person, whom would you like to meet?
52. What do you think about unfaithfulness in a relationship?
53. Do you think love at first sight is possible?
54. If your job started negatively impacting our relationship, what would you do?
55. Who is your favorite fictional character and why?
56. Do you prefer reading books or watching movies?
57. Do you have any regrets in life?
58. What is your ideal vacation?
59. Do you have a favorite movie?
60. If you are allowed to do just one thing for the rest of your life, what would it be?
61. What are some things about you that you take pride in?
62. What is the most courageous thing you have ever done in your life?
63. What is your earliest memory?
64. What do you like most about you?
65. Will you be OK with me hanging out with you and your friends?
66. If you could change something about your life, what would it be?
67. Have you ever taken dancing classes? Do you like to dance?
68. Do you think it is important to learn any form of a performing art?
69. What are you looking for in a relationship? In the long term or short term?
70. If you have three wishes, what do would you wish for?
71. Which is the song that makes you happy?
72. If you could have a superpower, what would be your superpower?
73. Who has been the most influential person for you so far in life?
74. Is there a movie that makes you cry no matter how many times you watch it?
75. If you could change one thing about yourself physically, what would it be?
76. What is the best advice you ever received?
77. What kind of music do you like?
78. If you had a previous relationship, why did your last relationship break up?
79. Are you still friends with that person?
80. What was a good moment in that relationship?
81. What are the craziest things that you’ve done with someone?
82. What will you have accomplished at work/school one year from now?
83. If you could go on a road trip where would you go?
84. What is the best part about family life?
85. What is a favorite memory you have of being with your family?
86. Tell me 3 good points about me.
87. What are your expectations of me in our relationship?
88. Did you ever want to kill someone?
89. Have you ever wanted something really bad and then later, not so much?
90. Is there anything I could do to make you think I am a bad person?
91. What would you do without electricity for 3 days?
92. Do you like to go shopping, not buying, shopping?
93. After I had asked you out for the first time, was there any part of you that wanted to say no?
94. Where are some places you like to go on dates that might be different from where we usually go?
95. What are your views on open relationships? Do you know what an open relationship is?
96. Have you ever thought of adopting a child?
97. Is money more important to you or are relationships you share with people more important?
98. What is it that you are passionate about?
99. Do you believe long distance relationships can work?
100. What are your thoughts right now about spending the rest of your life with just one partner?

Now that I have your attention :D I’d like to encourage you to read other posts in my blog. Type a word into the search box and see if I’ve posted anything related :) or make a topic suggestion in the comments! In my blog you’ll find stuff like this:


(before first date)

She was sitting at a table outside a Starbucks, reading a Psychology textbook smoking a cigarette (I had quit smoking about a year and a half earlier, go figure), but she was simply breath taking. It had been 5 or 6 years since I had been in a relationship, and I really wasn’t interested in another one, but I figured, what the heck, let’s find out who this person is, if she will talk to me, and if not, the worse she could tell me was to F off.

I approached her and stood on the other side of her table a few feet away. I said hello. She looked up at me, stared for a moment without a change in expression, said hi and turned her face back down into her textbook. Well, no F off. I proceeded with a logical question. What school do you go to? It seemed like a 5 minute wait, but it was probably more like 5 seconds, she was most certainly deciding if this was a question she really wanted to answer. Cal Poly, she said without looking up. Hmmm, well at least she answered :D

I went to Cal Poly :D So I told her that fact and that one of the reasons I went there was because my mother went there. No response from her. Quickly I added that another reason was because I liked to see the animals in between classes. No response from her again; strike two. Finally I said another reason I liked the school was because since it sat on a hill it was a good workout getting to and from class every day, so if I wasn’t able to make it to the gym later I wouldn’t feel so bad. She stopped reading. Bingo! :D

Her expression didn’t change, but at least she looked up, smiled briefly; then turned her head back down again into her textbook. No F off still! :D I pulled out the chair from across from her and sat down. I don’t remember the rest of the conversation other than she eventually closed her book and we actually had a pleasant conversation. She had recently moved out of her house, she was a part time student, and a part time model. After about 30 minutes or so I was feeling like this had turned out better than I could have believed when she surprised me. It was a Tuesday or Wednesday and she asked me what I was doing that coming Friday afternoon?

I am sure my pulse raced. I paused a moment. Nothing in particular I said, why do you ask?, I responded. She asked me if I would like to have dinner with her. I paused again, studying her. We had had a great conversation but she had been quite emotionless (something I would come to understand later) I did get a couple of smiles and a few laughs out of her, but for the most part her expression and the conversation were very serious, mostly about school and life in general. I sensed she had enjoyed our chat, but she was articulate, very smart, and stunningly beautiful. Her choices for dinner companionship were endless. An invitation to dinner from her to me caught me completely off guard. After thinking a moment I thought, sure, why not :D

First Date

Not one to be anything but myself I figured might as well let her know what kind of person I am right away. We met at a restaurant near the Starbucks. Don’t remember the name. I do remember we sat in a booth and the seats were leather :D We had some conversation and I was glad that she started by saying she had never asked a guy out before but she had really enjoyed our conversation a few days earlier and wanted to get to know me better. I thanked her and took a sugar pack, lined it up in front of me and flicked it across the table and caught the edge of her arm with it. Her expression was a mix of shock, anger, and incredulousness :D I grabbed another sugar pack and repeated :D Her expression intensified and before I could get a third sugar pack, she grabbed the container with the sugars/sweeteners and put it next to her on the booth seat, with some vigor :D

We sat in silence for a few moments then our drinks arrived. Her expression softened somewhat, and I could see she was still processing what happened and what to make of it :D I tore the end off of the straw wrapping and blew the rest of the wrapper at her, catching the corner of her forehead :D Her shocked, angry expression returned, but she quickly got her straw and did the same. I saw it coming and ducked so her paper missile hit the lady sitting behind us in the back of the head :D Not sure exactly what had struck her, the lady turned around quizzically and then turned back around :D My date was now shocked with herself; had her mouth agape, hand covering it, but then burst out into hysterical laughter. She had never done anything like that before :D

And so went the next couple of years :D

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276 Responses to Top 100 Questions to Ask Your Potential Boyfriend/Girlfriend

  1. CHAT says:

    I was studying some of your articles on this website and I conceive this site is rattling informative ! Keep posting .

  2. Page Popplewell says:

    Hey i read your list of questions and i like them a lot. i have made my own list and would like to share it with you i think you would fine my questions vary good. maby even add them to your list. were should i send them in a email or in a coment :) ty for u liar and time to make ur list.

  3. Page says:

    ty for your time and you list i love them have over 700 so far in my own list. :p

  4. sabrin2014b says:

    I read all them !! and I like !! THEY really helped me to clarify much more my life

  5. Mr Phiri says:

    Can I use the questions? I need your permission please.

  6. badr says:


  7. LOVE says:

    These are great for fun in letters too! Thanks (:

  8. budu says:

    Tanks a bunch

  9. judy says:

    Better late than never being informed

  10. judy says:

    Did your parents say you were to young to date and did you defy them and live to regret it?

  11. Aislinn says:


  12. Natalie says:

    I love this.

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