Spiritual and relationship expert, teacher, counselor, advisor, speaker, and writer James Gray Robinson

Dating: 10 Questions to Ask On Your First Date


It is important to get to know a potential romantic partner before you have sex or get too involved with them. While most people don’t want their first date to feel like a job interview, the truth is you can save yourself a lot of pain and suffering if you get just a few questions out of the way before you start getting serious about each other. You don’t have to pull out the questionnaire and fill in the blanks over lattes or pizza, but you need to work some initial background questions into your first date before you get too involved.


It goes without saying that your intuition plays a critical role in this investigative phase, primarily because if your date has a problem with these questions or exhibits great discomfort with answering them that should be a red flag. Similarly, if their answers don’t “ring true” then you should dig deeper before going further. You can simply weave these questions into your conversation and see where they lead you.


  1. Tell me about your parents. Sociologists tell us that our personalities and psyches are formed early in life, well before we turn 7 years old. Most of our beliefs and prejudices are established before that. Finding out the kind of parents your date has/had will tell you a lot about what is going on subconsciously with your date. If your date’s childhood was traumatic, there could be trouble ahead. That doesn’t mean everyone with a traumatic childhood has problems, but it certainly bears further questions. Most people learn how to handle relationships from their parents and that is a great clue about how they will handle your relationship.


  1. Tell me your best/worst childhood memory. This question is another way to inquire about their childhood/parenting experience. Their best childhood memory will clue you into what their aspirations are for family life. Their worst memory will give you a clue on how bad it can get with your relationship. If they don’t have any childhood memories, that is a big red flag because they are blocking their memories of childhood which could mean subconscious issue ahead.


  1. Tell me about your family chemistry. A great clue about your date’s social and relationship skills is how do they relate to their siblings or extended family. If they don’t get along with their family that is an indication of interpersonal issues or lack of parenting. You can be sure that if their family of origin is a mess then the chances of your relationship being deep and fulfilling are questionable. If any of the above three questions are ringing alarm bells, it may be wise to ask if they have ever had counseling. They may have survived and thrived.


  1. If money didn’t matter, what would you like to do as a career? Career counselors will always say find what you are passionate about and figure out how to monetize it. If your date is a barrista and they want to be a entrepreneur, you have something to build on. However, if they are a lawyer and want to join a band, you may have some existential angst on your hands. If all they want to do is be the Big Lebowski, then you may want to move on.


  1. What was your worst relationship? If your date has a horror story about their ex, then remember you may be the next ex as well. When I was a divorce lawyer, after listening carefully to my potential client’s tale of woe I would ask them what their ex was going to say about them. If they don’t have an answer to that, watch out. They are either hiding something or won’t take responsibility for their actions. Dating and relationships requires two adult people being open and honest with each other and if one can’t do that you are looking at an uphill climb.


  1. Can you share the remote? This is an indirect way of finding out how much control your date expects in the relationship. A successful relationship requires balance and compassion. If your date expects everything to be the way they want it (their way or the highway), best to find that out quickly. There are many relationships where one party gives up everything to be taken care of and their needs fulfilled. A friend recently told me that they don’t want an equal relationship, they wanted to stay at home and be a housewife for the rest of their life if they were provided for. I have my doubts about disempowerment as foundation for a relationship, but theoretically it could work.


  1. How much time do you spend on social media a day? Of course, if they have been texting all though your conversation (or you have), this is an indication of the answer to this question. I am a baby boomer, so I am not surgically attached to my smart device. If you have children at home you are checking on, that is one thing, but if they are conversing with the public during your date that shows their level of interest.


  1. Have you been tested for STD? Are you willing to be tested before we have sex? This is the white elephant in the living room question. Statistics indicate that over 60% of the public have been exposed to STD’s and may be active. Educate yourself about STD’s and insist that your date be tested before you have sex if that is important to you. People who don’t have STD’s won’t object for obvious reasons, but those who do will object for obvious reasons. If you have an STD, I recommend that you go ahead and get that out of the way and disclose that.


  1. What boundaries do you think are appropriate? If your date is needy or clingy then you need to come to some sort of agreement on boundaries. Do you want them going through your emails or texts? Do you want to have separate finances or joint finances? Do you think that four nights out drinking with their friends is too much? What do you expect in this relationship? Is it a committed partnership or a friendship with benefits? Are there any topics that are off limits? You can get into some great discussions if you are with the right partner. If it is the wrong partner you can have a quick cup of coffee and say good night.


  1. Have you ever had a broken heart? Why? This is a great way to get into what they expect from a date/partner. If someone broke their heart over some mouse turd reason then they may not be the adult you are looking for. How emotionally mature is this person? I have a very close friend who just wants to date women and not have a relationship with them, especially if he should compromise or give up any control over his life. He seems to be perfectly happy this way, but for the women who date him with hopes of making anything more of the relationship it has been like waves breaking on the cliffs.



Honestly, there are a few dozen more questions I would ask, but these ten will give you some idea whether you have hooked up with a keeper or a player. If you can bring any of these questions into your conversation, it will open into the others. It is important not to interrogate your date, that may make them feel overwhelmed. If you have some friends, try these out on them first to see how to integrate them into a conversation. A good relationship takes a village.

Reprinted from Sivana Spirit Magazine