A few Sundays ago, I turned 41. That day, I had a nice birthday dinner and a chocolate tart (the result of a mix-up — I asked for a torte — but lovely nonetheless). But I didn’t consider it to be much of a cause for celebration. I’ve actually been feeling pretty unhappy, at times bordering on (if not crossing into) depression, since the summer of last year, as the reality of my current situation has really started to set in. It seems somewhat shameful to complain; I should feel extremely lucky, having essentially fallen into my dream job right out of college (next February is my 20th anniversary at MIT, only five more years until I get the uncomfortable wooden chair!), and having no real material wants — but it’s not healthy to keep things bottled up, so I’m trying to put it into writing as best I can.

What follows has been percolating in various forms for a while. Some of it I have shared with one or two other people. It is a bit disjointed, a jumble of thoughts I still haven’t entirely sorted out even over the course of a year, and I haven’t necessarily followed every idea here to its conclusion. I am far from the world’s most facile writer, and these subjects are among the most difficult for me to write or even speak about.

I’ve always known I was an introvert, even before I had any understanding of the term. Growing up, I was never completely without friends, but neither can I recall any time, nor any place where my family lived, where I had more than one or two. When my parents moved, or I went to a new school, or circumstances changed in some other way, I lost touch with those people, and it took a long time before I would even meet another new person. Thanks to the magic of the Web, I can find out what many of these people are up to now, but I don’t feel especially compelled to try to reestablish contact; thirty years, or even twenty, represents a very great deal of water under the bridge, and I don’t expect that I would have anything in common with any of those people now, having so comprehensively forgotten them so long ago, beyond a bit of shared nostalgia. Perhaps this means they were not really friends, as I understand the word now, but my memory says I thought of them that way back then. Looking back, I was nearly always closer to the teachers and other adults in my life — especially science teacher Sister Rita Hammond at Mater Christi Elementary and French teacher Mrs. Nancy Provencher at Rice High School — than I was to people my own age. (Mme Provencher died two decades ago; Sr. Rita appears to still be alive, although I haven’t communicated with her since the sixth grade.)

Different people experience introversion in different ways. Growing up, I seemed to have it in spades, although a modern-day psychometric test doesn’t classify me as quite so profoundly introverted as I feel. I’m sure this was a result, at least in part, of the fact that I was always, from a very early age, large in body size, precocious, bookish, unathletic, and not particularly interested in games or sports, which severely limited my potential for socializing. (One of my earliest memories is getting told off, in the first grade, for laughing while reading a book that I “was not supposed to be able to understand”. The notion that one could find entertainment in a book without knowing what every single word meant was clearly foreign to that teacher.) Over time, this developed into an almost fanatical devotion to personal privacy — what I understood, most acutely, as not being observed. When circumstances put me into a public school for seventh grade, with mandatory physical education, after five years in a parochial elementary school with no phys. ed., I was the boy who hid in the bathroom stalls to change, when he even remembered to bring his gym clothes to school at all. Of course, I was also the boy who didn’t know the rules to any of the games that were played in gym class — and what twelve-year-old boy doesn’t know how to play baseball, basketball, or soccer? (After that year, it was back to parochial school, and I never again had a PE class, to the great detriment of my future health.)

When I went to college, the whole thing started again. I started my undergraduate career at Johns Hopkins, and had I remained there, the other members of my tiny freshman class (undergraduate classes at Hopkins were then only about 250 strong) might have become friends. There was very limited dormitory space on the Homewood campus, and private dorm rooms were very expensive, so I ended up in a double room, and I think there were some triples as well. Had I stayed at Hopkins, I would have had to get a roommate for sophomore year, when all undergraduates had to move into off-campus housing, but family finances did not allow for another $20,000 school year, and we had no conception then that I could take out a loan for such an enormous sum in my own name. I had gotten acquainted with some of the computer science instructors, one or two of the CS grad students, and some of the system administrators in the computer center, but lost touch with my actual classmates. I would never again have a roommate.

When I got back home, I got a job working in the warehouse side of a Service Merchandise in South Burlington. (Mr. Wheeler, the store manager, probably knew from the moment he saw me that I was not someone he wanted to put directly in front of customers.) The following fall, I went back to school — a much cheaper state school — as a continuing-education student, and formally transferred to UVM as a full-time student for the spring term. As a commuter student, I lived at home with my parents (just a short bike ride down what passed for busy arterial streets in South Burlington), so I was spared the mandatory dormitory living that my fellow students were subject to. Of course, this meant that I was completely cut off from campus social life, and the only other undergraduates I knew were the ones I met hanging out in the computer labs in Votey Hall.

When I moved to Massachusetts after college, the only people I knew were the people who had hired me. I also knew next to nothing about the area, despite having extended family not too far away, and didn’t have a clue where I ought to be living. In a rental housing market dominated by the September-to-June cycle of college students, there wasn’t much available, and I had no idea how ignorant Boston-area real-estate agents were of properties outside their immediate neighborhoods; I ended up in an uncomfortably hot one-bedroom apartment in Brighton, far away from any of the people I worked with, students or staff, most of whom lived near the MIT campus. I was lucky to meet Scott Fybush, one of the few lasting friendships I have ever had, while he was working at WBZ that first year; as I recall, we met for dinner at the California Pizza Kitchen that was then in Harvard Square, after which he drove me over to the WBZ studios for an impromptu tour. (I got to shake hands with David Brudnoy!)

What brought Scott and me together was the radio hobby, specifically DX’ing — listening for, logging, and eventually requesting written confirmation from, distant radio stations (AM stations, back then, which was more practical when noise levels were lower). I met a bunch more people through the radio hobby, many of whom I will still greet with pleasure on the rare occasions when I go to a radio-hobby convention, but none that I would really understand as “friends”. Scott and I started a Web site for Boston radio history, which I still run, and through that endeavor I did eventually get to meet a number of other people I do keep in touch with, particularly media historian and author Donna Halper. Scott and I did a whole bunch of traveling together, eventually culminating in what has become a nearly annual tradition of a “Big Trip”. But Scott and his girlfriend Lisa got married, then moved back to his hometown of Rochester, New York, so I rarely see him except on our pre-planned travels.

Aside from the radio hobby, I was very much involved in my job, and for my first decade in Boston most of my free time went to the FreeBSD Project, on which I was an early contributor and Core Team member. That work gave me a number of career opportunities — all of which I passed on, after that initial job at MIT — but with the center of gravity in the Bay Area it didn’t exactly help me meet people. Not that I was really concerned with meeting people back then — after all, I was only in my mid-20s, and besides, where would I find the time?

I had always assumed that I would someday meet someone I was interested in, as a potential mate — maybe a friend of a friend, or an indirect coworker — and would have the time and inclination to develop a real friendship before the subject of (serious) relationships ever came up. But that never happened. Oh, I met some smart, attractive women, and even some cute guys, but nothing ever came of it. Most I only ever met in the course of business; the few that I did have more of a connection with, I eventually found to be in relationships already (sometimes even married!) and never got any further. (Which is not to say that I completely dropped them — I’d like to sit down to dinner with any of them and talk about what’s happened with them over the past years — but I haven’t been good about keeping up with these people, particularly the majority who have moved away.) One thing I have noticed — only after a former co-worker pointed it out to me — is that we introverts tend to be terrible at recognizing kindred spirits, particularly those other introverts who are relatively successful at “passing” in our extrovert-dominated culture.

Over the past few years, it’s become blindingly obvious, even to me, that this approach isn’t working — particularly once I turned 40. Literature, music, and other media are of course no help; the sort of books I favor — even the ones that feature classically introverted main characters — tend toward the “True Pair” template. The music I like is very much in the same vein; there are no helpful models here. I don’t drink, so bars and clubs don’t do anything for me (indeed, I roundly detest the lot), and live-music venues, back when I did more of that, tended to the large and impersonal. Because of where I live and the schedule I keep, remaining in town after work to engage in other sorts of activities (that I’m told exist but don’t know anything about) where I might meet people is a high hurdle to cross, even when I can bear to put myself forward. All the while, I’ve seen the intersection of the sets of people I might be interested in, and of people who might possibly be interested in me, shrink and shrink to nearly nothing.

After a group luncheon some time in 2012, my officemate was talking about how she met her husband through an online dating service. That sounded like an ideal way to meet interesting people, if it worked as well as she said, safely, anonymously, and with a reasonable assurance of at least some common ground — but it still took me several months before I could bring myself to sign up. When I did, I found it to be rather less helpful than I first imagined: I could hardly bear to actually send messages to other people, or even take actions that would let them know I was interested, and when I did, the best I got was a polite refusal — the vast majority of messages received no response whatsoever. I asked my officemate to talk about her experience again, in private this time, and the pointlessness of the exercise struck me: she said that she gained a lot of confidence in the service from looking at how it thought she matched up with people she already knew. She didn’t have any trouble meeting people, she just needed a wider pool of people to find the one she wanted. I thought about her description of her experience, and compared it with my own, and concluded that dating sites, at best, benefit those who are already well-endowed with friendships and in most cases are going online after multiple experiences dating people they already knew from the offline world. I still log in from time to time and look at the profiles — even send messages occasionally, in the hope that someone will at least bother to respond — but it seems rather a fool’s enterprise for one such as me. Maybe, like dieting, it’s something you really have to “buy into”, and I just haven’t hit bottom yet.

One other thing that I noticed while using the dating site was how many people set their upper age limit (the oldest person they were willing to consider) at 39. When I hit 40, all of a sudden I had become too old. Another group of people set it at 40, so now that I’m 41, I’ve lost another big chunk of potential contacts. People don’t update their requirements all that often, even as they get older — but then, people don’t change their actual preferences all that often, either, and that’s on both sides of the equation.

A few months back, the CBC Radio 1 philosophy/documentary series “Ideas” did an episode where a speaker (part of a lecture event somewhere) talked about the economic perspective of dating as a barter transaction, in what is technically called a “double-coincidence market”. In a barter economy, for every transaction, both parties must be offering something that exactly satisfies a need of the other party’s. Once you introduce money, buyers and sellers can satisfy their needs independently — but of course society frowns on those sorts of transactions when it comes to dating, relationships, and, dare I say it, sex. And most people aren’t interested in that sort of a mercenary approach to relationships anyway; we all have dreams that that One True Partner will show up somewhere, somehow — like David Wilcox’s “huge blue poodle” (from “Metaphorical Reasons” on Live Songs and Stories, the intro to “That’s What the Lonely Is For”; go listen, I’ll wait).

So that brings us up to last summer. Scott and I did our “Big Trip” in Minnesota and the Dakotas, making a loop from Minneapolis (where there was a radio-hobby convention hosted at the Pavek Museum of Broadcasting) down through southern Minnesota and then up the I-29 corridor from Sioux Falls to Fargo and back to Minneapolis. The trip was a success by most any measure, and we got to meet a number of interesting people (Scott has numerous industry contacts) and take pictures of nearly everything. When I got back home, I immediately started thinking about where I wanted to go next. I only have five states left to go to bag all fifty, and my attention gravitated to the 49th state, Alaska. The airfares to Anchorage seemed amazingly reasonable, given the distance, and rental cars didn’t look too bad, either. Then I started looking at lodging, and was shocked at how much even dumpy chain hotels were getting in midsummer. I reluctantly came to the conclusion that there was absolutely no way I’d be going to Alaska unless I was sharing a bed with someone. That was pretty distressing, but it’s not like I hadn’t made the same conclusion about numerous other places I wanted to visit some day; I have a huge stack of foreign trips I’d like to take, but are either too expensive to do alone, are just wouldn’t be worth doing without someone to share the experience.

But it really got me thinking. In the 25 years since I had reached “dating age”, I had been truly, seriously interested in exactly one person — I think she knows who she is, but I’m not mentioning names — and that interest was not reciprocated. If it takes another 25 years to meet the next person, I’ll likely see my own parents pass on, even reach my own retirement, entirely alone, without any sort of companionship or emotional support. And of course there would be no chance of having a family of my own — if women of an appropriate age already aren’t interested in 40-year-old guys, they certainly aren’t interested in 60-year-old lifelong bachelors. (Nor, for that matter, would I want to bring another person into being without having at least reasonable confidence of living to see that child’s graduation.) This was a truly depressing thought, and reinforced how little time I really had left, and how much time I had wasted when all the people around me were pairing up and having children of their own. (Scott and Lisa have two; a couple of my co-workers have two each; and my next-older cousin has three.)

Then, the following Saturday, I was shopping for something — I think bed linens — and I got a surprise call from my father. He told me that his mother had had a massive heart attack, and they were waiting for all the immediate family members that could make it to get to the hospital room and say goodbye before the life support was turned off in accordance with her wishes. She died a few hours later, with her daughter and two of her three sons at her side. I was never very close to my father’s mother, but I was already primed for it to hit me hard. As a person of no particular faith, one of my greatest fears — perhaps the greatest fear — was that I would some day die alone and unremembered. Grandmother, who had lived alone for two decades after Gramps died, at least had her children at her side, and a week later, a memorial service with family and friends from her assisted-living community, then a cemetery plot next to her husband and her father-in-law. If things continue as they have (and assuming, of course, that I do not predecease my parents), I would have none of that. I might not even have anyone to notice that I had died. This was deeply, deeply depressing; I cried myself to sleep for about a week, and have felt even more incredibly lonely — when I haven’t been totally numb — ever since.

I don’t know what the answer is. Various nice and well-meaning people have tried to tell me, “Don’t worry, you’ll find someone eventually. Look, I was ${N} before I met my spouse…”. It’s incredibly difficult to believe that, given the experience that I’ve had so far. I do sometimes think that I’ve been too picky, that my preferences pretty much exclude anyone who might possibly be interested in me, but then I think it would be unfair to try to lower my standards and end up with a person I wasn’t actually interested in. (Maybe that explains all the women who seem to be active on dating sites for years without ever finding anyone: are they, also, too unwilling to lower their standards? There is some economics research on this point, which was mentioned in that Ideas episode I mentioned earlier.)