Best Dating Questions for Authentic Answers

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How to find love, how to ask the right questions. Shutterstock licensed image.


Dating Questions That Inspire Authenticity

Whether you’re running hot on OkCupid, Tinder, Bumble, Coffee Meets Bagel, Hinge, Happen, Clover, Plenty Of Fish, Match, eHarmony, or a newly trending dating app or site, it’s helpful to set a vision for your pursuit. It’s also vital that you have a game plan – especially for folks who are wildly sensitive, spiritually-minded, super-prayerful, or all of the above.

Whether you’re a healer, doctor, thinker, laborer, teacher, executive, manager, or just a down-right hard worker, we all need wonderful, loving, and aware partners in our lives. Throughout the process of seeking a lover or partner, it might feel easier to place the responsibility on the other person, but, truly, it’s up to each person to uplevel his/her/their sensibilities and awareness at the beginning of the hunt. The best way to do this is to prepare dating questions that inspire authentic answers.

Chemistry is nothing. It can be contrived.

Ego is nothing. It can mislead.

Mind and mental acuity are often nothing. They can misinform.


What drives value and longevity in relationships?

Sensitivity, quality communication, awareness, attention, loyalty, presence, and empathy. If you and your partner can commit to these things, you will find your lives to be uniquely loving and enjoyable.

1 – Let Your Dating Vision Inform the Best Dating Questions

When starting out, it’s important to write down a few thoughts – and commit to them. When forming your Dating Vision, consider these dating questions:

  • How do you like to feel when with your partner?
  • What are your partner’s primary attributes?
  • How will your partner respond to confrontation, feedback, and communication challenges?
  • How will you respond to confrontation, feedback, and communication challenges?
  • How will you celebrate and allow for your differences?
  • How will you and your potential partner respond to upheaval and surprises?
  • How will you and your potential partner communicate when one or both of you is angry?
  • Are you willing to skip sex while you’re dating?
  • What do you require from sex?
  • Which potential habits will you not allow in your potential partner?
  • Which habits are you working on so that you can be the best you can be in your new relationship?
  • What areas of your life and how are you stubborn?
  • Are you truly willing to improve yourself?
  • How forgiving are you? Can you be more forgiving?
  • If your partner is not a relationship leader, can you be the leader?
  • How important will empathy and compassion be in your new relationship?
  • Will you allow yourself to have sex with potential suitors – before really knowing them?
  • Will you be cautious or revealing during the early days of exploring your new relationship?
  • Are you willing to pursue dharmic relationships (in service to truth and soul evolution) versus karmic (contractual, need-based) ones?


Click to get The Personality Cards from Paul Wagner


2 – Your Dating Game Plan

When in pursuit of a partnership, especially a romantic one, it’s important to have a game plan and dating questions. Consider these questions:

  • Which apps will you use and which ones will you refrain from using? Why?
  • Will you be paying for meals or will the other person be paying? Or will you split the bills?
  • Will you pursue having meals together or only coffee at first?
  • Are you looking to just have fun or to find a truly wonderful partner?
  • How much effort every week are you willing to dedicate to this pursuit?
  • Will you be extra prayerful during this timeframe?


Your contract is not with individuals, it’s with the Universe.


3 – Getting Over Yourself

The most important thing we can do in life is getting over ourselves.

To have successful relationships with primary partners and lovers requires transparency, humility, and accepting that each of us has something to work on within ourselves. There is no “other.” Most often, the other person is not the problem. Mostly, we are resistant to change, we refuse to acknowledge that we can be more compassionate, and when it comes to listening, we can all be a little lazy.

The second most important skill we need to develop is forgiveness. This doesn’t mean we allow harmful people back into our lives, it means that we are able to release our anger and resentment upon most infractions.

Your ego is fiction.

Your temporary self-identity is fiction.

Release what is false.


4 – The Best Dating Questions For Pre-Dating Exploration

When we’re using an app to find love, it’s important to use the app to its full extent. One rule that you might find helpful is to never meet anybody unless you spend 1-month texting with them via the app. This is important so that you don’t quickly jump into projections and allow chemistry to override your sense of reality.

When exploring a potential partner, don’t pretend to be someone else. In fact, it’s best to lay all of your aspects out in the first several exchanges. This way, you and your partner can keep projection and fantasy to a dull roar. Focus on being authentic, even if it upsets the other person. Be fully yourself.

Here are 65 dating questions you can ask within your favorite dating apps BEFORE you meet for coffee:

  1. What do you find most enjoyable in life?
  2. What do you find to be the most beneficial definition of success?
  3. How do you resolve conflicts in your life?
  4. In what ways do you demonstrate love when in a relationship?
  5. In what ways are you selfish in relationships?
  6. How forgiving are you?
  7. How do you feel about the words fuck, twat, asshole, and mother fucker?
  8. When you see a child, do you often smile at him or her?
  9. Are you affectionate?
  10. How important is sex to you?
  11. What specifically is sex to you?
  12. How often do you need to have sex – after the 2-3 year mark – in a relationship?
  13. What is the wildest thing you’ve done?
  14. Have you ever been arrested?
  15. Have you ever been addicted to drugs or alcohol? If yes, tell me more about your recovery and current status.
  16. What is your concept of God?
  17. What is your concept of The Universe?
  18. What are your most self-improving habits?
  19. What types of healthy food do you love to eat?
  20. What types of junk food do you love to eat?
  21. Ever bite your fingernails? How about your toenails?!
  22. Ever have sex in a department store?
  23. How do you feel about traveling?
  24. What is the most adventurous thing you’ve done in your life?
  25. What is your longest relationship or marriage?
  26. Do you believe that aliens from other planets and galaxies are living on our planet?
  27. Ever do anything playful with your privates, like put it into a pie or watermelon? (it’s a movie reference!)
  28. Ever use something unusual to penetrate your vagina for pleasure?
  29. What is the most compassionate thing you’ve done in your life?
  30. How would you describe your level of empathy?
  31. Have you ever taken The Empath’s Oath?
  32. How have you resolved your most traumatizing events from childhood and your younger years?
  33. When something challenging happens to you, are you proactive or reactive?
  34. When it comes to intentionally improving your life, are you a warrior or a victim?
  35. Have you ever been molested or raped? If so, are you still angry or upset about it? Are you still broken in some way? Do you pray for that person? Have you forgiven them?
  36. On a scale of 1 to 10, how positive are you in your daily life?
  37. When you’re angry or grumpy, what do you do to improve your state of mind and heart?
  38. How do you feel about ceremonies, rituals, and prayers?
  39. Do you ever envision praying with your primary partner or lover?
  40. What are you generally willing to do so that you can improve your attitudes, feelings, moods, and demeanor?
  41. What are your most unique skills and talents?
  42. On a scale of 1 to 10, how much do you love being in nature?
  43. Are you vegetarian or vegan?
  44. Do you have any dietary restrictions?
  45. If you’re a meat-eater, have you ever hunted and killed your own animal food?
  46. Do you like to watch birds?
  47. Do you kill spiders that you find in the house or do you capture them and release them outside?
  48. Do you vote? Why or why not?
  49. Do you have a political party affiliation? If so, are you passionate about this party?
  50. What are your core beliefs (one sentence each) regarding welfare, minorities, immigration, free national health-care, and military spending?
  51. Have you ever traveled outside the US? If so, what is your favorite places to visit?
  52. What places in the US and Europe do you like to frequent?
  53. How do you serve or help others who are less fortunate?
  54. Do you invest money in the stock market, cryptocurrency, or anything related to your interests or passions?
  55. Do you like to garden?
  56. When you see a living creature flying or crawling on the ground near you, do you ever engage the little Being in conversation?
  57. When you pray, who do you pray to and what do you pray for?
  58. Do you believe in miracles? How so?
  59. What is the most lovely event that you’ve experienced so far in life?
  60. When you think about death, what comes to your mind and heart?
  61. Do you know the difference between co-dependent and co-interdependent?
  62. Are you willing to live co-interdependently, where each person seeks to uplift and encourage the other person to be self-sufficient?
  63. Are you willing to be in a relationship where there is no blame or shame, only patience and loving encouragement?
  64. Can you foresee a relationship that does not allow expectations and demands, and where there are only well-communicated agreements?
  65. Are you willing to commit to being peaceful and loving in all things, including yourself?


If you get push-back for wanting to only text for a while, say this:

“We’re all prone to poor decisions because of media influences throughout our lives. We’re all vulnerable. Each one of us needs some distance from images, perfume, charisma, intimacy tactics, and projection. Texting for a while helps a lot with these things. Also, I am a very open, kind, and emotionally-minded man. I love people from all walks of life. Choosing a partner for a life-long journey requires some deep exploration. It can be easy to fall into a relationship with someone for a myriad of reasons – some alignment, physical chemistry, passion, short-term connection, etc. With texting, we can explore some of the more pertinent questions, thereby accelerating the learning processes – without all the normal human distractions. Then we can determine whether it feels right to meet. This is akin to eHarmony, but without their contrived questionnaires and chemistry hooks. It’s real, it’s authentic, and it works for both parties – long term.”


You are the only person you ever interact with. There is no other.

“Don’t find fault with anyone. Not even with an insect. As you pray to God for devotion, so also pray that you may not find fault with anyone. Never think that you alone have true understanding and others are fools. One must love all, No one is a stranger. It is Hari alone who dwells in all beings. Nothing exists without Him”  – Bhagvan Sri Ramakrishna


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