First Date Cheat Sheet
Dear Maxwells: I’ve been blindsided too many times in my dating life. People seem one way and then I discover that they are not the person I thought they were. This wastes time and energy. Can you give me some questions to ask on the first couple dates that would help me vet somebody in a much more efficient fashion so I don’t end up being blindsided again?
Dear Reader, thank you for your question, and yes, you are touching on something massively important about dating that we will address in today's column. The basic cannon of questions that people fall into in the early stages of dating only scratch the surface of what people really need to be looking for in a potential mate. “What do you do?” What are you looking for?” “What are you passionate about?” “What was your upbringing like?” As well as some of the more lighthearted dating questions that are so pervasive like “what’s your favorite food, place you’ve traveled etc.” do very little to actually help you get to know somebody and know whether you want to continue to get to know somebody. We aren’t saying that you shouldn’t ask these basic questions, but if the buck stops there, then yes, it would be easy to be blindsighted later on. In fact, these basic questions should happen organically in the first few dates as they are easy to reach for and part of the natural flow of conversation. What we can offer you today is a cheat sheet of a few really great questions that should one hundred percent be in your repertoire for your first few dates.
The first question that we tell all our single clients to ask is “what was your parents' marriage like, and how did their relationship inform or influence your own beliefs about love?” This is a stellar question, if we do say so ourselves. The reason being because it accomplishes a number of important things simultaneously. The first thing it does is help you make sure that whoever is sitting across from you has a modicum of self-awareness and intelligence. If somebody says “well gee, I’ve never thought about that before” what that tells you is that they haven’t spent much time reflecting on themselves or their upbringing which is a red flag for sure. How somebody answers this will also demonstrate their emotional intelligence, their ability to connect the influence of their past to their current place in life. The third thing it will do is automatically deepen the level of conversation between the two of you. You will learn about their childhood and if it was a healthy one or not. And more importantly, if it wasn’t a healthy one, you will learn very quickly if they have learned from it, and taken proactive steps to grow from it and understand it, or not. If they speak like a victim of their childhood, that is also a red flag. If they speak like somebody who has alchemized a bad situation, that is a very positive sign. This question also helps you understand immediately, what somebody ultimately believes about love and relationships, which is a glimpse of how they will act in this area in the future as our underlying beliefs govern all our thoughts, feelings and actions. This question also gives you the opportunity to discuss your own childhood and beliefs as well.
The second question that we recommend is “what are the biggest lessons you feel you’ve learned about yourself from your past relationships?” Again, this question will accomplish a number of things at the same time. It will give you an understanding of whether or not somebody has taken responsibility for their role in the dissolution of their past relationships versus blaming their exes for why they broke up. It will force you both to go deep very quickly and discuss a potentially triggering topic at the get go, versus later on, and will also help you understand some of their past patterns around love and dating which, if left unchecked, are only bound to repeat themselves. Hopefully, it will also help you understand whether or not somebody has cheated or been cheated on (most people have) and what they have learned from it and how they plan to navigate the world of sexual contracts and monogamy or non-monogamy moving forward.
The third question that we recommend is “What is the biggest lie you’ve ever told?” We’ve written at length in this column over the years about the importance of honesty and transparency in relationships and that without those two things, a relationship is like a house with no foundation and is at risk of all sorts of systemic issues. How they answer this question will reveal somebody’s beliefs around what lying is. Everybody has lied at some point in their life, and our ability to own the lie, and understand why we lied, and what we learnt from it, is an indication of our propensity to lie in the future, or not. Additionally, this should naturally open up a dialogue about the importance of honesty in relationships and provide an opportunity for you both to align on the principle of honesty in relationships as a cornerstone of success.
The last question that we tell our clients to ask is “what are currently, some of the main things that you are working on improving about yourself these days, and, what are your methods of working on them?” In addition to honesty and transparency as essentials for relationship success, if you are dating, it is a must that both you and whoever you are considering as a potential partner are dedicated to your own personal growth and evolution and that you are taking steps to tend to that area of your life on a consistent basis. Like honesty and transparency, this is also a linchpin in successful long term relationships. This question directly addresses whether somebody is of that mindset or not, as well as their relationship with modalities like therapy, coaching, spirituality and other forms of personal growth. Start asking these four questions on your first couple dates and you will accelerate so much in your dating process, saving time, energy and ultimately attracting your ideal partner.
