Dateless-Man vs. Caretaking (And Other Related Things)

It’s a new year, whether you, me, or the New York Giants want it or not. This time around my inspiration to blog actually comes from an article which is about a month old. I considered double-posting in December, but since I sometimes struggle to maintain a “one entry a month” average lately, I didn’t want to rob myself of a relevant topic. And as the weeks have gone on, it actually became more relevant with certain developments regarding “My Oldest Female Friend,” who hasn’t gotten a mention in this space since October 2020. This is a non-fiction blog so I don’t set out to have things ebb and flow, but sometimes the natural course of life shifts that way.

And no, I haven’t gotten laid. I am still the captain of the Virgin Airlines Space Shuttle, on its way to planet Untouched in the Chaste Nebula, despite pushing 42. But that kind of topic will come up later on.

Onto the article. To the surprise of few who follow this space, it’s one of the Q&A columns from the only online dating guru I’ve ever followed or put much stock in — the very wise, yet very flawed, Harris O’Malley/Doctor Nerdlove (DNL). It relates to a column from December 20th (2023), and it isn’t even about the lead writer. For those in the comments, most of his Q&A columns (which make up the bulk of his free content lately) feature two letter writers, or “LWs.” The first is always LW1 and the second is always LW2. Now that some of the jargon is out of the way, I took immediate notice of LW2, who was nicknamed “Blokeless On The Coast.” O’Malley will often give letter writers a nickname to hide their identities, and that’s the best he could come up with a week before Christmas.

Without reposting the entire letter, it gained my attention for two reasons: it featured an example of the kind of women who are now within my “dating cohort,” and she had a life experience similar to my own. “BOTC” said she is 36 years old and while she is not a virgin, but she hadn’t had sex since her son was conceived, which was when she was about 20. In all of that time she has not only been raising a son while working multiple jobs, she has also been the caretaker for several of her elderly relatives and effectively has had no dating (and little of a social life) in all that time. Her letter was about having nervous breakdowns and crying fits anytime she interacts with her siblings, and she is worried she will make a scene at her kid sister’s wedding. The advice which DNL and many of those in the comments went on was that her problem wasn’t being single, but it was her extreme burnout for being a caretaker for almost two decades and she needed to resolve that problem first and just de-stress before even bothering to date anyone. He and they offered a variety of “remedies” for this.

The letter really made me think just how long I, myself, have been a caretaker (or co-caretaker) to a relative and just how stressful as well as emotionally, physically, and financially draining it can be. One of the major motivations for starting this blog in July 2014 (yes, nearly a full decade ago) was to create a record of my woeful or non-existent attempts at romance onto another medium besides my mind, to create a body of evidence that I wasn’t just a garden variety failure. I was uniquely burdened with a variety of romantic disadvantages and inefficiencies which rendered me unable, incapable, or even unwilling to have any success with women on any fundamental way beyond platonic friendship (which is no small thing which I do appreciate). And while most of those examples were about myself personally — my lack of confidence, or charisma, nor dashing looks or coordination — it made me wonder just how much I have glossed over this very real, and significant chunk of my life. And most importantly, its effects.

When I was young, I was raised by my divorced, single mother who worked to support us. My aunt lived in New Jersey and aside for occasional sleepovers and mailed presents, I rarely interacted with her. My only other available relative was my maternal grandmother, who lived about an hour’s train ride away. Once she started being unable to maintain her bills (coupled with various ailments, from thyroid issues to losing her vision to breaking bones in falls), my mother started taking care of her when I was in my early teens. For most of junior high and high school, in fact, grandma unofficially shared a room with me on a spare, smaller bed which was there just for her visits. As I grew, so did my responsibilities. And before I was through with high school, my own mother’s health started to fail due to a variety of things (including fibromyalgia and a fall of her own), until she began legally handicapped at the end of the 90s (when I was 17). So not only was I helping her with grandma, I was helping her, period. It wasn’t so easy to be a carefree teenager, only focused on girls, parties, or other things. I couldn’t so easily or avidly attend functions, or spend dwindling resources.

One clear example was at the start of college when some of my friends went on two annual “ski trips” which were just excuses to go out of state to a ski lodge, get plastered, and in most cases get laid with similarly snockered women. It required a $1000 deposit from everyone who went, and I couldn’t blow that kind of money for so frivolous a thing. Add in the fact that I didn’t like excessively boozing nor fared well at bars or clubs (which I attributed for decades as “me being lame,” not merely being an introvert), and that was just the most obvious example off the top of my head. The other was that I almost always had to clear things with “the family” before I did anything beyond a routine, local hangout session at a pal’s house. It wasn’t just because I was shy or anti-social, but because real events happened. Very soon into college, after grandmother deteriorated further, my mother and I had to arrange for home health aides, which was so nightmarish a process that eventually my mother just lived with grandma full time for about 2 years. And during that period I was aiding on the weekends as well as trying to land or keep jobs. By the time grandma did pass in early 2010 (at age 89), my mother’s health was failing further, and I still had to find steady work.

I can say for most of the last 13 years I have worked steady, and most of that time was with two companies (including the place where I work now). But caretaking for my mother got no easier even before she was diagnosed with colon cancer in late 2021, with a years long and well documented eviction battle against the landlord during a good chunk of that time. Beyond the loss of time or careful accounting of finite resources, it was easy to fall into a routine of coping. Dating has always been a stressful, unrewarding, miserable experience for me, atop a life where free time for anything which was not work or chore related had to be carefully structured.

These are problems most of my friends did not face. Most of them came from steady, middle class, two-parent households where they could easily save money to move out because they never had to cover expenses like rent, food, or utilities (even well into their 20s). Their parents never fell apart physically in their teens. They never considered things like orange juice luxuries for years of time. I am not saying they’re all millionaires in lives of luxury, but they faced at least one or two less hurdles toward settling down with a wife and kids than I did. Maybe a good chunk of my problem wasn’t that they’d cracked a code and I didn’t; maybe they simply had fewer chains around their bodies.

Most of the recommended “solutions” for BOTC did frustrate me because they’re mostly made out of well intended ignorance. The biggest is “negotiate with other family members to share responsibilities.” That makes perfect sense…if humans were genuinely good and honest creatures, and families were not usually collections of mismatched people linked by circumstances and genetics. Most families with siblings not only do not share caretaker responsibilities, but refuse to. In most families where this becomes an issue, one person is designated as “the caretaker,” and it all is heaped on them for convenience. My aunt had a car, a house, and far more income, yet she did virtually nothing to tend to her own mother; she deliberately left it to her older, handicapped, poorer sister because it was more convenient. My grandmother’s relatives, who are mostly “performance-Christians” who live in California and are upper middle class, had been telling her to take care of herself anytime she asked for help by phone or mail, going back to the 1970s. And that is how most families, or at least native born, American white families tend to treat each other. Most of the time, that “designated relative” is a woman; a daughter, aunt, sister, mother, etc. My situation is rare. But then again, there’s no choice. I am an only child. It was either caretake or leave my mother to die, and I cannot do that.

In other communities, there can be some more sharing. As an example, in most nursing homes in America, it is very rare to find people of Asian, African American, or Latino backgrounds. The “clients” are predominantly white people, and it isn’t just because of finances. It is because white people are trained from cradle to grave to only care about “number one,” and that old people are only worth what they can give you monetarily. When they can’t or if they never could, they’re abandoned to their fate so the next generation can thrive. And having been to many nursing homes and/or recovery homes for the elderly over the past 20 years off and on due to caretaking, I can honestly say that prison inmates are better taken care of. At least if enough inmates die or are mistreated long enough, eventually they will get attention. The elderly in America are so badly mistreated that on AARP article I read last year indicated that many detectives don’t even bother to investigate their deaths for any signs of crime or trauma unless it is bullet hole/stab wound obvious. Even if someone is in their 60s, has bruising, and a ransacked apartment, the general opinion of most precincts is, “eh, they’re old, they fell over.” That is usually how occasional “elder killers” can seem to pass through gated communities, hospitals, or nursing homes for years and no one connects the dots. No one darn well cares.

At some point in 2016, I once reached out to one of my best friends (who is of Asian-Polish/Jewish descent) for some aid, even if emotional support, with my mother and I. Her health was bad that month and I was afraid she’d die and leave me in worse straights. And his words, over Facebook messenger, still haunt me. To paraphrase: “I’m not afraid she’ll die. I am afraid she’ll live another 20 years and by the time she dies, it will be too late for you to have your own life.” He then recommended I toss her in a nursing home and “visit every week.” I knew at that point to never ask him for help again, and I haven’t.

I also related to BOTC because of her age in relation to mine, and the fact that her life’s history wasn’t so atypical. Not every single woman over 30 is some stereotype of “SEX IN THE CITY.” In fact, most aren’t. Here is someone who is 36 (well within my stated age range) who may have gone on fewer dates in the last 16 years than I have with a teenage son, and her own caretaker war stories. I imagines myself meeting someone with that kind of experience, and would I be willing to date her if we clicked. My answer to myself was, “sure,” with the caveat that I can’t be a caretaker of two households while being understanding and supportive.

Now, you would think that my experience as a caretaker would make me seem, at least, sympathetic to single women. Many are in that situation or know someone who is, and in theory it means I am at least capable of things like responsibility or balancing a budget. You would be wrong, and I do truly believe it is a regional thing. In the south or more midwestern areas, I might get more mileage as a romantic partner over that…the only problem are the women in those parts tend to skew more conservative than I am. And in New York, it isn’t that my tales of being a caretaker to an elderly mother aren’t met with some compliments, but it immediately takes me off the table as a viable romantic paramour. No one thinks “41 year old man taking care of his cancer stricken mother” and goes, “That is the kind of man whose penis I want inside me,” at least not unless he is painted like Fabio on the cover of a romance novel or looks like one of the “Marvel Chrises” (Chris Evans, Chris Hemsworth or Chris Pratt), or isn’t able to ooze raw charisma despite all that skin to James Bond. I am just “such a sweet guy,” and women don’t sleep with sweet men. They sleep with fun men. And despite my own sense of humor and jokes, beneath it all I am a nerd with too many responsibilities running him ragged. I am, at best, a woman’s boyfriend’s wacky pal.

There’s the practical challenges of caretaking, too. Every every person I go to or place I visit on a date, especially in a post-Covid world, risks exposing my cancer-stricken mother with new germs. For an easy example, I now have enough money and paid vacation days to be able to go to Las Vegas and finally become a man via one of the many legal brothels. At this point I am no longer morally opposed to it; I may as well lose my virginity like a circus freak might. But I cannot even do this because between two airports, two airplanes, a new city with a lower per capita vaccination rate, and the experience itself, I am almost assured to bring back either Covid or a nasty flu back home. I could, in theory, afford my own apartment now (which wasn’t true until last year), but I cannot afford two. If and when I move, my mother has to come with me. Even if I won first prize in the lottery tomorrow, I couldn’t just retire while riding a giant robotic T-Rex pulling a pool full of Swedish bikini models. I would have to make sure my mother is stable wherever she is first, and I’d at least have to check in.

So, that article inspired a lot of thoughts about my current options, or lack of one, as well as whether or not I would be willing to date someone with a similar life experience as I.

Now, onto the current developments with my long-time “female friend,” Sonia (whose name I type here is an alias). She’s since resumed Facebook chat contact with me a few months ago, after a period of years when she hadn’t. As I stated in the 2020 recap, she is facing her own health woes, despite being younger than I am. I thought back then it was some kind of cancer but she and her doctors are not sure. Right now she is a few month removed from a rehab facility, where she has gained a lot of weight, is almost bedridden and cannot work. She is trying to get social security disability benefits, which was a fight even in the 90s when mom applied (and waited about 2 years to be approved). She is currently living with her latest of a string of abusive boyfriends, out of a lack of anywhere else to go. I’ve chronicled some of the tragedies of her life, but they include having her father die when she was very young and being molested for years by her uncle (who her mother defended). Despite being bisexual, she has mostly dated men and every one of her relationships seems to grow abusive. I know at this point many would say, “maybe the problem is her,” but I have known her since the 90s and I can say her only “problem” is being vulnerable and a lot of men exploit that in women. Maybe that is how so many avoid being older virgins like me.

Admittedly, her latest reach-out involved something she does semi-annually; ask for money out of desperation for some basic stuff. I rarely was able to help out with that in the past due to being broke, but this time I could genuinely spare it (after all, I can casually drop cash on DVD binges pretty often). I don’t think the two are linked but it is a coincidence. Some other friends have come to me for help online, since this is the “Kickstarter for Life Woes,” generation we are all in, and I have been able to help a little with some without harming myself or my mother. Another friend of mine lost her common law fiance last year, for example, and I helped pay for the funeral. If I thought I was being suckered for cash I would have cut contact with her ages ago. I do not; I only see someone in need.

Since she is a long time friend, I have enjoyed having her back in my life to talk daily (or every other day). Once problem, or at least one major difference, is she is the only one of my friends who avidly asks about my love life. At this point I may remind readers who don’t have as perfect a memory for my posts as the Marvel Cinematic Universe expects of its films that Sonia is, to date, the only live actual woman I have ever known who admitted to once having a crush on me. Not asking for a date, but once telling me, “I liked you.” The problem is she has always been out of state, or far from me, and/or living with a boyfriend. Despite the reputation from my friends that she was “loose,” she does not cheat on her boyfriends (and if she did, it wouldn’t be with me, because I am not that mercenary).

Sonia is the first person in years who has asked me flat out if I was “still a virgin.” Despite having told myself and this blog I would not lie if asked that directly, I balked on the question and replied, “I don’t want to talk about it,” which I guess is enough of an admission. More to the point, Sonia has made more passes at me and being fairly straightforward that she finds me attractive and wants to sleep with me at least once. This is a drastic change from where things were even 3 years ago. At one point, unsolicited, she sent me a video of her exposing her breasts, which I guess is the closest I have come to a “sext” outside of text roleplay with fictional characters. A few times I mentioned having to speak sternly to callers at the call center I used to work for and Sonia has gone on about how “sexy” that seems. She has become very flattering, almost too much for me.

I suppose at least one person has reached this point and asked, “So why haven’t you slept with her, you crazy moron?”

The first is that I am not going to sleep with a nearly bed-bound woman who is currently living in her boyfriend’s house while said boyfriend and his mother are living there. That is diving crotch first into a love triangle situation which has a risk of ending with an episode of DATELINE NBC where Keith Morrison is narrating the murder of one of us in his usual annoying folksy dialect. The second is that Sonia needs a solid and supportive lifestyle and I am not certain that I can provide that, and if we sleep together that will just jerk her around. It isn’t that she has gained weight; it is that she, too, sort of needs a caretaker. I cannot caretake for two people, and even if my mother was not around any more, I find myself hesitant to leap from one caretaking assignment to another. It isn’t as if I would be opposed to being a caretaker for a spouse or significant other if we grew older together — I would. But the idea of never getting a break from having to do that, since the time I was maybe 16-17, until the day I drop dead is giving me pause. Is that wrong? Does that make me evil or terrible? To want a break from that? Just for, like a year or so between whenever my mother passes and my first lover, ever? Is that so terrible? Or should I just risk being shot or stalked by a pissed boyfriend just to lose my V-Card to a friend? Is it worth that kind of drama?

I don’t think so, so I haven’t. But to not blog about it when it clearly links up to the start of the entry and is very relevant bordered on malpractice.

This weekend I am going to hang out with some friends for the first time in over a year and I am really looking forward to it. No romantic opportunities, just something social, and not related to any jobs, on the clock or otherwise. Where I can just…be for a while. I didn’t realize how much I missed that kind of thing until I lost it.

Maybe I, too, don’t need a girlfriend as much as a life of my own, but a life of my own not at the expense of the one who gave me life. And that’s the riddle.

Thanks for reading.

As always, I remain…the Dateless-Man.