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What to Look For on a Date

There is obviously a lot we could be looking for while on a date. But if we are looking to find a long-term partner, some of the things that would be most beneficial to know–some things that would determine if our life in the future with them would be much happier or much sadder–are the hardest to find out. We would love to know how emotionally mature someone is, because that would have a huge effect on any future relationship with them. We would love to know if someone is going to appear one way but be completely different after a year or two. And we would love to know–which is the hardest to find out–how someone will grow over time. Because in a long-term relationship, it is not about having zero flaws or a non-existent dark side that matters; we all have it. Rather, it is the ability to grow and grow together that is the basis for finding fulfillment with one other.

But how to find out such things on a date? When the conversation is flowing and you are laughing together, it’s hard to drop in: “So, how emotionally mature would you say you are?” or, “Do you have another side of yourself that you are completely hiding from me; even hiding, in fact, from yourself?” Such questions probably have the effect of making the questioner look socially incapable.

One way to do it is to make provocative comments and to look out for certain signals, or green flags. For example, if you end up discussing someone in the public spotlight who fell from grace (in a moderate way), you could say, “yes, well I guess we all have it in us to be assholes”–and see how your date responds. If they acknowledge the dark side in all people, that’s a good sign. It likely means they are not suppressing as much within themselves (another side of them that could come out in a few years). We all have our shadow sides; much better to be aware of one’s own, than unaware.

Or, if at some point you find yourself discussing your date’s past actions, it’s interesting to notice if they are occasionally embarrassed by aspects of who they used to be. For people who are growing and learning (instead of always clinging to old patterns), it is natural to find previous experiences a bit painful. A date finding pain in their past is a good sign.

We can never know exactly what it’ll be like to be with anyone in the long run, but making a list of the green flags to watch out for in the early days is a good start.

Image: Untitled, 2019, Volodymyr

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Jack Fuller

Jack is a depth therapist and the founder of Archive. He has a doctorate in theology from Oxford University and a degree in neuroscience from Melbourne University. He is the co-author of The Imagination Machine (Harvard Business Press, 2022)