20 Best Dating Questions

After this brief but important introduction, I will quickly go over the list, without much embellishment, then afterwards, I will go over best practices for using the list.  I plan to do a video presentation of this material so check the Metaphysics Today YouTube channel for the video of this list which will include a little more explanatory content. 

Let me open by saying this content if for quality people looking for quality relationships.  This dating advice can apply to straight or gay folks.  It also applies to people who are dating over 40 as well as people who have previously been married. It is not about how you like to do it or with which gender you are attracted to for love or how old or ‘around the block’ you are.  These are about the heart and mind, and enduring, potentially deeply fulfilling, quality romantic, life mate level relationships.

If you are the type (or are experimenting with being the type) of person who just desires lusty, crusty couplings, then this  message is not for you. However, If you are even the slightest bit interested in marrying someday, especially to start a family, you would be wise to take your dating time seriously.  Why? Because people can be upset and damaged by bad non committed relationships arguably just as deeply as by committed relationships gone sour. Why let unworthy people mess you up even before you meet your life mate?  

With the prevalence of incurable venereal diseases, curable but damaging venereal diseases, and seemingly more and more crazy people – what with all the prescribed and non-prescribed medications people take these days – roaming the earth, and the high cost of dating and living- why expose yourself to so much *hit when there is only a limited amount of shinola out there for you?

Here I will teach you how to quickly screen and move on from obvious from the gate,  ‘go nowhere’ potential couplings, so you can save your heart, mind, and body from the life grinding sludge heap of junk you will otherwise expose yourself to – and get gunked up by – for no good reason.

So, let’s get started…


One of the most powerful indicators of whether you are dating someone worth your time is how they choose to respond to even being asked these types of questions I present here.  If someone responds with something like, ‘hey’ i’m just interested in keeping it light’ or ‘I’m not comfortable with talking about these types of personal questions’ or ‘ hey, lets just have some fun and see what happens’, know you are wasting your time with someone who does not share your goals and who probably sleeps around.  Why pick up all their collected physical and spiritual heebeegeebies? Why do you deserve that? Even if this used to be you, why go backwards to these kinds of shallow people? You’d just be setting yourself back, no doubt for nothing that will be worth it in the end.

This is not an anti sex talk.  Sex is great. However, the proof is out there that too much casual sex is harmful in many ways to both men and women.  Scoff if you wish, but deep down you know it’s true. Freedom to enjoy casual sex goes well beyond birth control. There is still the emotional, spiritual, social, and physical ramifications of sleeping around, just because your horny, or trying to prove to yourself or others that you are ‘free’ and can do what you like. That just does not add up to a healthy and wise outcome.  

Now, let’s go over the 20 questions to ask a new man or woman during the first few dates:

  1. How do you spend your down time?
  2. What makes you laugh?
  3. What are your long term goals?
  4. What is something on your bucket list?
  5. What is your relationship like with your parents?
  6. Are you hoping for a relationship or just fun?
  7. What do you value most in a relationship?
  8. What quality is most attractive to you in a partner?
  9. Name three things you would like to have in common with your partner?
  10. For what in life do you feel most grateful?
  11. Do you like animals / plants as part of your home environment?
  12. What do you believe is your worst quality?
  13. What is one thing you will not tolerate in a relationship?
  14. Are you family oriented?
  15. What is your biggest strength?
  16. What is your biggest weakness?
  17. Are you a grudge holder?
  18. Are you spiteful or vengeful?
  19. What is the longest relationship you have been in and how did it end?
  20. How do you nurture your own spirituality?

These are not the only important questions to ask prior to engagement or marriage, these are just the questions to ask to filter out people you do not need to ever take seriously for purposes of becoming a life mate.  For hundreds more questions and dozens of topics which need to be asked prior to marriage get a copy of this book, THE LIFE MATE QUESTIONS: 600 Questions and Topics to Consider and Ask for Happily Ever After, by Cathleen Vaune Carr available on Amazon.com 

Okay, back to these 20 Dating Questions…

These 20 questions have been carefully curated to not be construed by an otherwise well intentioned, quality person, as being too intrusive.  A quality person will immediately understand your reason for inquiry without you even having to explain yourself. If they are open to the same outcome as you they will be grateful to have the subjects broached, so they too, do not have to waste their valuable time.  This is a fair approach because it gives both parties 20 chances up front to determine if more time, money, and energy need be invested.

Let’s be clear, you do not need to ask all these questions on the first date. That would be ridiculous and accurately perceived as desperate. Pace yourself and learn more about the strategy for doing so later in this message.

Understand, I have not put these 20 questions into any particular order, mostly because I know each of you has our own priorities and must follow how our own mind works.  So, you can put them in to whatever order makes the most sense to you, then when the conversation feels right, ask one question only, then LISTEN carefully to the answer.

If you do not understand what the verb ‘to listen’ truly means, immediately read a few articles, posts or books on the subject.  Next meditate on HOW TO LISTEN, until you can actually LISTEN to another person while they are speaking to you.  

After your date has finished speaking, and you have taken a moment to consider what they have said, then ask clarifying questions if you did not understand them completely. Also, and this is important,… pause and wait to see if they ask you the same or similar question. This step is important because it will reveal whether this person is self centered and/ or perhaps not interested enough in you to care. Does not it stand to reason that if they are interested in you, or at least interested in not wasting their own time, they would want to know about your answers to these same questions?

Then and only then, move on to question #2 on your list, if it feels right to do so.  Otherwise, leave the next question for another time. Chances are, there is absolutely no need to rush.  The last thing you want is for someone to feel he or she is being interrogated because you cannot stop asking questions. Breathe and relax yourself if you find yourself becoming anxious. Its okay to feel excited, but do not let your excitement ruin your chances of being positively perceived. At this stage of the proceedings, (notice I did not say ‘game’, games are for players – and you are more respectable than that, right?) it will be hard to come back from a show of bad form if you let anxiety or poorly managed excitement get the best of you.  

Another good method of approaching these questions at a reasonable pace is to  allow yourself no more than a few questions per date.  That gives you at least several more dates with this person and a fair chance of getting a real feel for them, and them for you, while you are doing your ‘homework’. Keep your pants on and only go to places where you can talk that do not cost lots of money and do not have a strong romantic vibe until you are satisfied that this person is worth more substantial investment.  This applies equally to the other person regarding you.

Now, the reason I mention money, is that many people feel ‘owed’ or ‘pressured’ when the expenditure of money becomes too excessive  (dependent on the respective parties means) early on in a dating environment. So rather than get into ‘value’ judgment issues, just keep money out of it in the first place.  Frankly, if a person is only going to go out with you if you are going to spend lots of money, well there’s a big hint right there that they are not smitten with you, but rather with what you can provide to him or her.  I’ll leave it up to you to figure out how that makes you feel. I’m not judging you, just warning you.

Next, after you and your date have gotten past the 20 questions, you have two sensible options you can avail yourselves of  to help you resolve the next set of most important questions; those being whether you and / or your date are wired for commitment and marriage. Trust me, not every one is.  That does not mean they are not a nice person or even a great friend and lover.  It means they do not do well in confining relationships or relationships that require a lot of focused devotion on another person.  this could be for many reasons.  I can help you easily sort this issue out with a Commitment / Marriage Ability Consultation. Also, if after your happily  past the early dating stage, and later have run into problems, I can still help you with my 1 Question email consult.  Both of these services- and others -are explained in detail here on the MetaphysicsLessons.com website.

So there you have it. So here you get the goods and how to use them in one place.  It is wise of you to be smart about your heart!  Remember, these are 20 questions that can save you time, money, and heartache while you are on one of the most important journeys of your life – the hunt for a life mate. Happy hunting!

Wishing you all the best!

Dr. Vaune

WORTH A WATCH! My Conscious Valentine https://www.youtube.com/watch?v=D02Bvo7I-44

Copyright 2019

All Rights Reserved

Dating: Greg and Amber – Is he interested?

Background:  Greg is 26 and Amber is 25, and they met at a wedding brunch hosted by mutual friends.  They were seated beside one another, chatted amiably enough, discovering that they shared a passion for fine art and culture. Greg mentioned a museum show he’d just gotten word about and they agreed to go together after work the next week. They paid for their own tickets, enjoyed the show, liked the conversation and agreed to keep in touch.  After a few casual, public get togethers thereafter, sometimes with or without other friends along, Amber decided she was ready to establish physical contact. Greg had not made any moves in this regard and Amber knew she had not let on that she was smitten. So, she invited Greg to her home after a movie they attended with several mutual friends.  Greg made a plausible excuse why he could not go, but invited her to a live art installation the following week. He made no move to kiss her good night, not even a hug was offered, and he left. They enjoy talking to one another, but the conversation never becomes flirty or intimate. Greg is straight as far as Amber can tell and so are his friends.

The Problem: They continue to date, but he always politely declines private invitations that could lead to intimacy and never extends one.  Neither of them has initiated physical contact of any kind. Amber is physically attracted to Greg and has developed affectionate feelings for him and is desiring a romantic relationship.  She does not want to scare him off by making a move or broaching the subject because she enjoys and values the friendship.


The Question:  How can Amber find out whether she is wasting her time with a man who is not ‘into’ her romantically?


Dr. Vaune’s Advice:  An indirect approach will be best in this situation.  Amber could first ask someone who will be discrete if Greg is romantically interested in her.  If that is not possible, then she could ask Greg if he is currently seeing anyone romantically.  His response will signal whether or not she should inquire further. By that I mean, if he is, then she has her answer as to why he has kept her at arm’s length.  The upside here is that his behaviour suggests he is not a player; that he respects himself, his romantic partner, and Amber. On the other hand if he is not otherwise involved, she could follow up with light hearted questions about his romantic past like, “Have you ever been in love?”, “What was your favorite romantic relationship like?”, or “Do you keep in touch with any of your old girlfriends?”, etc.  His answers might give clues as to his nature and availability without her having to dive right in with, “Are you attracted to me?”, or similar. If it makes sense after he answers those example questions, Amber could ask, “When was your last romantic relationship?” Maybe Greg is still getting over a bad or heart breaking relationship and is simply not ready to get emotionally involved with anyone yet. If Amber is genuinely interested in Greg,  it is worth asking the questions that can perhaps help him talk about the subject or at least get some answers for her to work with. It could be that Greg just likes her as a friend. Though that would be disappointing, at least she has a friend who enjoys her company and is not abusing her heart or taking advantage of her sexual vulnerability. Not every man is a ‘hoe’ and some of them make excellent friends!


Copyright 2019

All Rights Reserved