Overthinking It: Why I’m Not Online Dating

Recently a small group of single, Catholic, professional fellows of my acquaintance were sitting around, having some beverages, and doing what all single men do of an evening, when there are no ladies present, which is talk about women, and why we didn’t seem to be having much success in that area.  A friend of a friend happened to join us, and suggested that we approach online dating as a way of meeting single Catholic women around town whom we might not otherwise run into.  The argument was rational: everyone tends to work more than they play as they get older, people don’t all live in the city, and the opportunities for meeting other singles can become fewer and fewer.  His advocacy on behalf of online dating was a reasonably logical one, particularly after the Meursault had been polished off.

The real problem was that I was hugely skeptical, and for good reason: I had tried online dating before, a number of years ago.  Despite dating several intelligent, successful, attractive women, all of whom had been interested in going out again, it just didn’t work.  In retrospect, I think relationships never developed largely because none of them held the same values I did, and because we had no friends in common at all.

Nevertheless, despite my doubts about what I was doing, the next morning after our conversation about giving it a try once again, I sat down and opened an account on the popular online dating site which had been suggested the night before.

In order to create a profile, I had to answer many dozens of questions.  The vast majority of these questions were, quite frankly, obscene in nature, or dealt with drug use, which I have never engaged in.  At the conclusion of this lengthy and rather prurient questioning process, the site did its business, and determined several things about me.

On one side of the equation – er, algorithm – I tended toward being old-fashioned, ambitious, spiritual, capitalistic, pure, friendly to strangers, and compassionate.  On the other, I tended NOT to be trusting, experienced in life, spontaneous, adventurous, kinky, sex-driven, or progressive.  I assume that being “experienced in life” in this context means something other than having skied in the Alps or tried escargot, both of which I *have* done.

Having received my results, it was now time to move on to the matching stage of the proceedings.  Naturally I was curious to see the results, wondering whether there was someone who had been under my nose the entire time that, for whatever reason, I had not run into before.  Unfortunately, not only were the results disappointing, but they started to have a problematic effect.

The matches were, first of all, mostly not Catholics, even when a 99% match was indicated.  I’m not closed to the possibility of dating someone from another faith, but the entire point of this effort was to try to find some previously-unknown local female practitioners of popery; I only later found out that I would have to pay an extra fee to get to that level of detail.  Second, the matching functions of the site started connecting me to ladies who, quite honestly, I wasn’t attracted to.

Now before I’m accused of blatant misogyny, let it be said that no one is better than I am at sitting down and providing a list of my many physical and personal imperfections.  I’m no paragon of anything.  However, I will unapologetically admit that I’m more likely to look twice at a lady who makes an effort to put her best foot forward, as the saying goes.  So much of civilization was built on the extolling of feminine beauty, that we (mere) males are hardwired to seek beauty out.

The disappointment in not finding any Catholic women I was attracted to among the matches was compounded when I started receiving notifications from ladies who had looked at my profile, and sent me personal messages or other indications of their approval.  In due course, this lead to a sense of guilt, which only grew worse as the days went by.  Should I be responding to these ladies in some way, since they took a chance and reached out to me? Would it be rude not to? So what if I didn’t find them attractive – shouldn’t I just be grateful someone thought I was attractive and interesting enough to want to know more about me?  Something which had started out as an experiment, was turning into a moral dilemma.

In the end, I realized that the solution was something which a very dear friend tells me from time to time, and which my spiritual director himself told me only a week ago: stop overthinking it.

Overthinking is an occasional occupational hazard for some, but particularly for those of us who advise, write, and talk for a living.  We try to see all the possible answers to a problem, and consider them in turn.  In certain contexts, this is actually an extremely useful skill, whether you are drafting a complex business contract, or planning for a large birthday party.

Yet more often than not in your personal life, the simplest answer is often the best: rather like getting dressed in the morning.  I’ve learned over the years that my first instinct in what I pull out of the wardrobe is usually the right one.  Instead of trying to re-imagine what shirt goes with what suit or tie, I simply stop thinking about it, and go with the first option I originally chose.  Almost inevitably, what my gut told me at the beginning turns out to be the right way to go.

So in the end, I deleted my profile from the dating site, and am back to where I started, albeit a little bit wiser for the experience.  Online dating works for some people, but not for me, because clearly it’s an occasion to overthink everything and accomplish nothing.  I’m grateful to the ladies who took the time to have a look-see over my profile, but from now on I’m going to stick to the old-fashioned way of meeting the ladies I date, which is largely through people I already know, and places and activities that matter to me.

Detail of "A Merry Party" by Simon de Vos Walker Art Museum, Baltimore

Detail of “A Merry Party” by Simon de Vos
Walker Art Museum, Baltimore

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Media and the Promise of Friendship

With the annual Conservative Political Action Conference (“CPAC”) about to get underway here in Washington, many of those in attendance will have their first opportunity to meet in real life those whom they have come to know via new media, such as blogging and podcasting, and via social media, such as Facebook and Twitter.  No doubt some people will be thrilled to finally meet each other in person, and their shared experiences at the conference will provide them with opportunities to cement their relationships.  Others, however, will probably come away disappointed to discover that the person whom they thought they liked is not as interesting or attractive a personality in real life as they are online.

We might make a reasonable observation that two people who have certain interests, views, or background experiences in common are more likely to form a friendship than those who have little or nothing in common.  Yet it is true for this scrivener at least that the older one gets the more one comes to realize that commonality is no guarantee of affinity.  No doubt many of my readers have had the experience I have, of introducing two of one’s friends to each other for the first time, thinking that they will get along well because they both have the same favorite food, sports team, or film, as well as our friendship in common.  And then one is horribly embarrassed to find that, after a few minutes, there is an awkwardness because the two are not really well-suited to one another after all.

The use of new and social media can make things even more of a muddle, because the interaction begins with, and may in many cases always be limited to, words written or spoken on a screen.  You may enjoy someone’s tweets about history, or reading someone’s blog posts about cooking, and interacting with them about these things.  And over time you may come to think that you have thereby formed a friendship with the author of those tweets or posts.  Yet if and when you finally do meet them in person, you may find that although you still like them, there may not be enough of a connection between the two of you to sustain anything more than a warm acquaintanceship, similar to one you might have with a long-standing barber, tailor, or bank manager, which never evolves into an actual friendship.

If the creation of a friendship was an easily predictable phenomenon, akin to the rising of the sun or the phases of the moon, I suspect there would be little or no need for the use of new and social media to reach out and try to make new friendships.  If 1+1 always = 2 in this regard, we would simply be able to meet someone for the first time and say, “Because you like the music of Mahler, you must therefore be my friend,” and that would be the end of it.  Yet look how often even the most fundamental matters that shape our entire world view – religion, nationality, ethnicity, etc. – are no guarantee that someone will become our friend.

To save everyone a lot of heartache, let us admit to ourselves that we have no idea why some people become our friends, and some do not.  There are always people whom we are attracted to, and whom we would like to call our friends, but they for whatever reason do not share that attraction.  The reverse can also be true, when we feel put-upon by someone who is trying desperately to become our friend when really we are fine with remaining acquaintances, and are just trying to be polite and not hurt their feelings.  And although not the subject of today’s blog post, it goes without saying that when that uneven level of attraction is not one of friendship, but romantic in nature, things can become even more complicated.

These kinds of awkward situations are initially masked in both new and social media, because the online personae we create for ourselves can be as genuine or false, as improved-upon or warts-and-all, as we wish, since in most cases there is little or no chance that we will actually meet the other online person.  Those with a more dishonest personality, or some aspect of themselves they feel they have to hide, can take advantage of this situation in a way which they would not be able to do in a dinner party setting, for example, after the wine gets flowing and tongues begin to loosen in conversation.  As such, while not discounting the possibility that friendships can be formed from a tweet, or from podcast feedback, or the like, we need to be realistic in our assessment of them as gauges of potential friendship.

Fretting over the uncertainty that is the formation of a friendship is as useless as trying to figure out why one of your children loves broccoli, and the other goes into a screaming fit if you try to make him eat it.  Some aspects of human behavior simply have no rational basis of explanation other than the fact that we are all individuals with free will, who can make choices for ourselves that defy expectations.  Putting together two people with common interests may lead to the formation of a friendship, but it may not, and the cut-to-the-chase aspect of both new and social media, where we come to believe we actually know someone well whom we have never actually met, can prove to be a great disappointment if not approached with some caution.

So before you spill your guts at CPAC to that person with whom you exchanged online barbs about Newt Gingrich, gentle reader, take a moment to reflect on what you actually know about them.  Are you in the process of making a real friend, or are you tying an albatross around your neck which you will come to regret?  Friendships rarely form instantaneously, and the possibility of making a friend, rather than an acquaintance, exclusively through the use of media seems to me very remote.  While I am a user and advocate of both new and social media, I would urge you not to mistake online relationships for real-life ones, which take much longer to build, and require more than keystrokes.


Detail of “Portrait of Two Friends” by Jacopo Pontormo (1522)
Collezione Vittorio Cini, Venice