What to do on a Date

Note: This post began as a Saturday morning exercise in flexing my creative muscles, with equal efforts at humor and insight, but in the end I’m not entirely sure it succeeds in either, but I’m still going to leave it here in its original form as it fulfilled its original goal of getting me started in writing in a particular way, and it may be a fun read for some people.

With all the modesty that comes from the simple recognition of the fact that I am no dating guru (“guru” being a term that is only hesitantly paired with adjectives describing professions, and the rare occasions when it is nevertheless considered applicable, it should only cause us to turn wary, as everyday professionals working honest jobs like electrical engineers or math professors hardly associate themselves with the word “guru”, a word carrying in its meaning a beguiling mix of spiritual mysticism promising hard-to-acquire life truths and a straightforward suspicion of everything that must be taken on faith), I want to write a few words on what a good date might look like. I don’t want to talk about what you should wear or whether you should offer to pay for the two of you or if you ought to reveal unbidden with a certain self-satisfied glee that you have recently become the proud owner of a shamefully unaffordable batmobile, and therefore consider yourself somewhat of a superhero. These are questions to which there can be no universal answer. Although, as I pen these beautiful thoughts, my infallible spidey-sense tells me that there must be a clear answer to the batmobile dilemma.

I think a great place to start is the beginning. The typical date begins with great promise—two souls have confirmed a mutual attraction, solved the coordination problem of meeting at a set time and place, and approach with nervous excitement the journey of finding out more about the other. But what is it really that we want to find out? Are we naive and expecting a confirmation of all our idealized projections on this person we barely know? Or, are we slightly more realistic, but not much more so, and approach with open curiosity, wishing to find out what they do on the weekends and what their hobbies are, in order to carefully file away these answers in our capacious mental bank, returning home from the date with smugness at our unquestionable talent in turning it into a ritual not unlike a systematic examiner coaxing answers to a survey questionnaire from an obedient respondent. Factual answers to such straightforward questions carry the illusion of being the kind of knowledge we want to be in possession of. It does seem at first glance that what we really want to find out about the other person is whether they too enjoy kite surfing, despite a quiet voice of reason bringing up our resounding lack of success in finding someone special at that recent bootcamp for surfers in Hawaii. This suggests that such crude questions pose serious problems for our knowledge-seeking quest. It is like attempting to perform brain surgery with a sledgehammer. The doctor, despite his best intents, will end up killing the patient. Instead of delivering certain death, we want to mimic the finesse of a scalpel, prising apart the mystery of our date with small, purposeful tools that will restore a sense of fascination to the whole process. The brain, after all, is extremely complex, as every good doctor knows. In the same way that we may come to glean more about a novel by asking the author a probing and open-ended question such as what prompted them to write it as opposed to asking them what color the book jacket is. We are after all clever people who know not to judge a book by its cover! So a good place to start would be as simple as asking them what they did this week. In their answers, if we are careful, we can find a great deal more than by inquiring about their hobbies. Perhaps they are unusually reserved about it, and instead of mechanically continuing to the next inquiry, we can gently ask them if they are shy for some reason. Maybe they tell us that they visited Italy over the weekend, and instead of nailing down the precise list of cities they were in, we might ask if they travel often and why that might be the case. Really, what we want to be doing is tracing an outline of the features comprising their particular and unique personality. We are cartographers patiently exploring the unknown with our delicate instruments to triangulate positions and carry our journey forward with adequate regard to what we have found out thus far, paying utmost attention to the curving coastline or the ragged cliffs, and setting the course for the future with these discoveries in mind; much can be discerned about the lay of the land if we arrive with no particular plan other than to let the landscape guide our journey. As good listeners, we keep our probing questions short and open-ended, for it is in the answers to such queries that we can come to learn how they see the world, and where their talents might lie. In essence, it is of far greater importance to learn that they are given to a certain basic kindness than that they are a virtuoso pianist, a talent that may be better appreciated by the concertmaster of a Symphony Orchestra than simple fools like ourselves.

Over the course of a few dates, we also want to figure out where their weaknesses might lie. This can and should be done without adopting the role of an interviewer performing a critical appraisal of a candidate against whom we are secretly harboring, perhaps—and rather terrifyingly—unknown even to ourselves, some twisted interest in watching them flounder, in a pathetic attempt to bolster our own strengths in such light. No that is stupid. Rather, we want to approach with a compassion arising from the secure knowledge that we are all rather mad in one way or another. This is a very tricky thing to do, and certainly not be conducted without sufficient tact; that is unless our date is an enlightened and wholly self-aware being who is not in the least ashamed of truthfully broaching the topic of how they may be completely absurd in some ways—a quality we can’t really count upon. Perhaps one way to go about doing this business is not to ask any questions at all but freely share our own faults first, whose knowledge we came to acquire through a great deal of painstaking introspection. And surely in their response to such fearless transparency on our part, we can find extraordinary truths about themselves than we could otherwise imagine.

So let’s say all goes well, we find them beautiful, sensitive, intelligent, and can hardly wait to declare that we like them, holding forth the naive idea that hearing that would make them exceptionally happy, for, after all, having spent adequate time enjoying their company and having been witness to their weaknesses, it is one of the more discerning compliments to confer on someone: a statement that says, I see you as you are and I like you for exactly that. However, a premature declaration of this sort can have adverse consequences for one major reason: by telling someone that you like them too soon, that is before you have had a chance to pick out a few signals confirming that such sentiments are reciprocated, you are condemning them with the burden of spoken knowledge that cannot be plausibly denied in the way non-verbal cues can. It is natural to wonder why creating this particular kind of concrete common knowledge could be a burden as opposed to a simple, well-meaning compliment. It goes something like this. From then on, either they choose to not see you again, and must therefore live with the pain and guilt of being responsible for causing someone who likes them some amount of suffering, or they do see you again, but then it is always tinged, even in their minds, with the idea that perhaps the liking is not necessarily offered willingly, and even the slightest doubt of this kind concerning the nature of whatever shared sentiment that exists is sufficient to destroy it completely, for in a romantic relationship there is no such thing as unconditional love; romantic love simply cannot be coerced. So it would be best to not say it at a time when we are uncertain whether they like us back.

One of the crucial ideas that ought to inform all our actions ought to be balance. Much like how everything I have said so far applies to any social interaction, balance too applies equally well outside the realm of a romantic date. It is a psychological cornerstone that is hardly ever properly appreciated. It is the distillation of a great many characteristics that we like in people into a higher-order principle. If we are to properly spend time studying what it is that draws us to someone we know well we would arrive invariably arrive at this idea. Every personality trait has a natural opposite (boring-unpredictable, vulnerable-strong, playful-serious, patient-decisive, relatable-intelligent, nonchalant-attentive) and really what we want to do is walk the Buddhist Middle Way simultaneously across all these dimensions. That’s balance. The interesting person is one who has managed to integrate the opposites into an irresistible concoction of excellent psychological health.

I want to end by circling back to the first point I made about opening conversations with a simple question about the recent past and listening with careful attention. One of the other great advantages with this prescription, besides restoring that all-important sense of fascination to the date, is that it naturally places intimate and deeper knowledge about ourselves and our date in the context of a longer conversation giving it the space and consideration that it deserves. Providing such information to our date as an answer to a pointed query, or even worse, unbidden, will make us seem rather foolish for either it indicates a lack of sensitivity to truly appreciate the depth of what we have just shared or a troubling impatience to hurry this process and get to the end of it by divulging facts in an inappropriate and disconnected way, which only serves to destroy the sense of fascination that a naturally flowing conversation would produce. For those among us who are a cross between an open book and a deep thinker, we need to be careful to not let our unhesitating inclination to share details of our lives pair with the dangerous explanatory power of our intelligent minds. A simple question from our date, can then turn into a lecture, which despite its immaculate honesty and articulate delivery, will reveal far too much information outside the narrow range of interest evinced by the question. We may start to answer the question by beginning from when we were six years old and how everything that happened since was inevitable through a long-winded argumentation sequencing many pieces of information into a series of logical deductions. And then we can be sure that we are doomed, for extended logical deduction by one party is no fun in a two player game of conversation: we want to be aiming at answering precisely the posed question before handing the mic over. Doing something more is bound to have negative marginal utility as unwanted information in the form of a lengthy monologue seeking forced entry into our date’s head will cause them immense pain. An indisputable scientific fact corroborated by a pair of bleeding ears. Let’s not do that. Let’s be nicer instead.

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