On First Dates & Asking the Right Questions

While a first date may be considered successful if your partner considers you witty, charming, intelligent, and despite your earnest protests to the contrary, good looking; the most important indicator of a successful first date is connection.

It is unfortunately the case that much of our lives are – to perhaps too great an extent – quite superficial and that we rarely connect as humans with open hearts and open minds. We talk, but do not communicate. It is not for nothing that communicate shares an etymological root with commune.

While we may not reveal much of who we are to people we know well, it is especially so when we begin dating. We keep much of ourselves hidden (for fear of rebuke) and pretend to be calm and composed even when troubles in the home or heart leave us feeling confused and in need of a good hug.

Seeing as the first date is somewhat an audition for the emotional capacities of the soul on the other side of the table, first dates are an opportunity to ignore a tendency towards obfuscation and be honest in a way that we rarely are about who we are.

With this in mind, it becomes clear that questions about what someone does, what they like, or what is their favourite film or book, are focusing energy in the wrong direction. While they may be stepping stones in conversation, they say next to nothing about who someone really is; their passions, desires, regrets, dreams and fears.

We often play on the surface of life, but truly getting to know someone requires depth. The first date requires us to start thinking and speaking differently. We need to learn the art of the date.

We want someone who will know (and respect) us for who we are deep down, but that is only possible if we ask the right questions. Questions such as,

When was the last time you cried, and why?

We focus incessantly on the positive aspects of one’s life. But everyone experiences pain, grief and sorrow; they just often keep it to themselves because it doesn’t get so many likes on an Instagram post. Asking such a question shows that you aren’t so tawdry and banal, and are interested in the part of your date that they don’t often show to the world.

If you lived your life a second time, what would be one thing you would have done differently?

In asking this, you show a concern not just for what is the case, but for what could have been. It shows an interest not in success, but in failure, regret, and disappointment. In drawing out the conflict between who someone is and who they wished they could have been, you will learn more than you ever could have asking about their book collection or Spotify playlist.

What frightens you?

Everyone appears (at least on the first date) infinitely more composed and self-possessed than we are. This question is an invitation to draw out the weakness that lies buried within all of us and to reflect together on how we may share the same fears and insecurities.

Do you want more from your life? What is it?

We all yearn for something more than what we have. We are, by nature, creatures of thirst, striving to reach new goals, ideals, standards, and new versions of ourselves. In asking this, you demonstrate an interest in what makes your date’s life meaningful. Nobody is fully content, and in finding out what someone considers as lacking, you get a good indication of what is important to them.

These questions seem depressing. But, in another way, they are attempts to dive deeper into another’s soul. It is a misjudgement to think that a question about crying will put someone off just because it is about tears rather than rainbows. Perhaps that will put some people off, but would you want to date someone so superficial? It is significantly more rewarding to be emotional yet insightful, than mildly amusing yet dull.

At the end of your encounter, your date may turn to you and inform you that they have never been asked so many insightful questions about who they are as a person before. What you have demonstrated is that you are interested, not in the surface play of life, but in whom they are as a unique, complex, human being with wants, wishes, desires, and regrets.

The unfolding origami of the soul becomes more enchanting with each layer that is peeled away, revealing the complex interconnecting forms which make us who we are. There is nothing more seductive than someone who is keenly interested in getting to know who we really are as a person. It is something infinitely more seductive than money, power, fame, or looks.

The beauty of these questions is in the act of self-revelation and in finding that your date at the other side of the table is still there, listening attentively and sharing their own stories, accepting you for the humble, awkward, damaged person you are, appreciating how you extend the same generosity to them.

Some other questions:

  • What qualities in your friends do you admire most?
  • When you think about your childhood, what do you feel was missing?
  • What are you addicted to?
  • What are you worried about at the moment?
  • Do you think the people around you know you for who you really are?
  • Do you ever feel like an impostor?
  • What do you want to change about yourself?
  • What part of yourself do you never want to lose?
  • When you think about what makes a good life, what comes to mind?   

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