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

20 thoughts on “Overthinking It: Why I’m Not Online Dating

  1. You’re a braver man than me, Billy. I’ve not tried online dating, and I don’t think I’ll ever try it. Admittedly, I’m satisfied where I’m at. If someone comes along who has common interests and values with me, perhaps sparks will fly and something may blossom. But in the meantime, I’ll just keep doing what I’m doing. It’s all Soli Deo Gloria, to borrow a phrase from the American Guild of Organists.

    Pax et bonum,
    Lyn x


    • Thanks for reading, Lyn! I don’t think it’s a question of bravery, just a willingness to try something in my case which, as my gut told me, was not the right way for me to go about doing it. I know people who have met their spouses this way, so I’m not knocking it AT ALL. It’s just not for me.


  2. I don’t even know where to begin so I will throw out the thoughts listicle style!
    – I’d assumed in this day and age of online dating, that it was easy for folks to find each other based on mutual interests. After all, there are pretty faces in Twitter avis, facebook profiles, etc. Obviously this isn’t the case!
    – I was tickled to see that your falls 100% in line with the readings from yesterday. How God sees our hearts vs how we see each other, vastly different things!
    – I’ve friends that are women and had them bemoan the lack of available good men. I ask them where they are seeking them and they shrug…bars, clubs, etc. Note, these are good people but not often Catholic. I don’t know what the answer is but I’m confident you will find it. You have your stuff together and good grief, if my FB friends are any indicator of how things are out there, that’s half the battle right there!
    – I wasn’t a hmm how can I say this? When I first met my wife, I wasn’t the best Catholic. Heck, now I am not the best Catholic, but I am a better Catholic now than then! (I’m involved in my parish, do our website, volunteer when and where I can) There’s more. When I met my wife we immediately discussed pro-life issues, but she was an evangelical and kept an open mind to conversion. I didn’t push it, in fact, the closest I came was giving her a Catholic bible and asking her to go to Mass with me. Something miraculous happened along the way, one of her radio shows disappeared or went off air or something…and she filed the gap with Catholic answers live as she went about her duties as CFO and COO of our household.
    Long story short, two years ago after RCIA and discernment and prayer she converted. As a Protestant she was a better Catholic than I was and pushed me to a better Catholic. Your results may vary, however I feel I must share this with you! Cheers!


    • Wow, thanks for all the great points! Again, I think this has to do with what works for you. I’ve tried this method, and it doesn’t work for me. Do I absolutely have to date a Catholic girl? No! But does it make things a bit easier? Absolutely. So we’ll see where things lead. Thanks very much for reading!


  3. Hi Billy! This is very interesting, because my husband and I were just discussing this very topic. When he and I met, online dating sites and certainly social media were not what they are today. Back then, I fretted so much over finding someone, and was so relieved when I found my one and only. 🙂 Since then, I have thought to myself, “Social media must make the whole process of finding someone with common interests so much easier!” Well…I certainly see and appreciate your point. My husband and I met through mutual friends, and although we don’t share the Catholic faith (now 😉 I have high hopes for this intention in the future!) there is much to be said about beginning on a foundation of friendship like that. It adds a lot of depth and outside support to your relationship as you get to know each other.

    Good luck, my friend. I’m certain things are going to turn out wonderfully for you. 🙂


  4. Interesting and thanks for sharing! I never ventured into the “online dating” scene, though many of my female friends in #cathsorority have met their spouses in one of those formats (OKCupid, CatholicMatch, etc). Of course, I did meet my soon-to-be-husband online…but Twitter is a different story, not to mention neither of us were there looking for dates, and he wasn’t Catholic at the time. My, how life changes when we least expect it! 🙂

    I hear you on the overthinking thing. Boy, do I hear you on that one.


    • Thanks for reading and sharing that! I think there’s certainly good that come from online relationships of course! But in this instance it just doesn’t work for me. Overthinking is definitely one of the reasons it’s the case. 🙂


  5. Interesting to hear from the male point of view. I attract enough how shall I put it nicely “eccentrics” that I don’t need the internet to widen that pool.
    Here in Arkansas there is a smaller pool of Catholics. Dating outside the faith, has been disappointing. The few times I was in a relationship where we progressed to the thinking about getting engaged stage all of a sudden the “open minded” men of faith I had been dating basically gave me a choice: their religion or we were through. Sigh.
    Good luck on the dating front!


  6. So you’re intelligent, cultured, have a profitable career, a wide range of interests, a deep Catholic faith as your North Star and guiding light, and (I’m sure a guy can say this without getting looked at sideways) you’re handsome. In another day, you’d have had incredible market value for marriage. In 2014, the age of 50 Shades of Gray and wives who dump their husbands of 20 years for the knucklehead three doors down and think nothing of it, forget it. I know a lot of guys in your shoes who’ve come up snake eyes in wife hunting. I know thugs with a virtual harem, and unemployed guys who get their girlfriends to loan them gas money to go spend quality time with his baby-mama (I’m thinking of a recent co-worker who gave her guy her utility bill money so he could do just that). Since I live almost in Chicago I seriously entertain the notion of learning where the Poles here on work visas hang out so I can get an Old Country unAmericanized woman to marry, marinated in the old Catholic culture where dumping a husband is a shame and not “you go grrrrl,” where a guy becomes husband and father and she has his back. Comedian Eddie Murphy put it best 20 years ago with his “Umfufu” routine.

    Don’t feel guilt over not responding to interest in your profile. I’m sure you sent your share of messages that were never answered, and they’re not fretting over you. It’s not misogyny, it’s discernment. There is a physical part of a relationship, and if you have no attraction to a woman but date her anyway, she will feel it and resent you. That’s a lot more patronizing than simply saying no, and it really isn’t fair – let her find the man who she turns on instead of grabbing her up because you feel required. Having a woman in agreement on religious and cultural issues is crucial when you raise your kids and have an ally instead of a competitor.

    Here’s what we’re up against – two quick tales. Pray for me and I’ll pray for you. Kipling nailed it in “The Female of the Species.”



    • Thanks for reading, and for sharing the thoughts as well as the kind words. Keep in mind that as the Gospel said this weekend, not as man says does God see! I have a lot to work on, quite a lot. But I’m hopeful and the good lesson of this experience was to trust my instinct telling me, “This isn’t for you,” not because it’s wrong for everyone, but because it doesn’t suit me. Thanks again!


  7. typical male superficiality and entitlement. lets see, from your photo youre an 7.5. i bet you feel entitled to an 8 or above. you better have some serious cash.


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