Dateless-Man vs. Sex Island

It’s a new year, and I am still cringing from an old one. Just a few updates and then something I would have typed a post about last year, had life not been more pressing. For the moment, the eviction proceeding that I’d faced since May 2018 is over. It was discontinued without prejudice, which means the landlord lost, yet is free to try again, which he will. Considering this ends the involvement of my former union attorney (who began the case when I still worked for the city and thus had to continue aiding me, even 4 months after I’d been axed), a fact the landlord bragged to my mother that he is aware of, this could be a case of winning a battle but losing the war. But for now, a respite.

In better news, the new gig I got around mid-November is still around. The training is over and I am officially on the telephones now. After some first day jitters things are going about as well as can be expected. I am still green in terms of the company, but that’s expected. I haven’t had any supervisor meetings about performance, which are common in call center jobs. My immediate supervisor briefly claimed I was “near the top of my class” but I am trying not to get ahead of myself. I am trying to take it one week at a time and while a permanent gig there would be terrific — the job isn’t hard and the commute is a dream — I thought ahead at the last job and that cost me. For now I’ll ride this out until April or May and anything beyond that is a gift. I’ve seen what happens when I dare think of a future for myself, again and again.

There actually is one co-worker who I trained with who is definitely my type, but as with the previous gig, I usually consider co-workers off limits. I used to get angst ridden about fellow college classmates, but that was due to inexperience and nerves. Dating co-workers may be common, but it’s also something that even veteran “playahs” admit takes more skill to navigate without making people uncomfortable, being fired, or causing office gossip. We haven’t chatted as much as “Dinah” and I had at my last job, but she is definitely my type. Part of the problem is unlike with Dinah, our desks aren’t nearby and we never talk without 3rd or 4th wheels. But, again, it’s usually a bad idea to pursue co-workers. Really the only beneficial side to this is it helps prove that I am flexible with the types of women I consider attractive. Some men tend to date certain “types;” for example, my pal “Tee” typically only dates fellow Italian-Americans such as himself. My other friend, a Jewish-Asian-American, tended to mostly date those with similar Jewish roots. On the other hand I have another pal who has dated mostly white women, but was getting pretty steady with a woman of color the last we met. Now I can’t back any of my own flexibility up with actual relationships, since I’ve never had one. But the last two co-workers I considered my type were not the same as some of the women I’ve written about in past adventures — who were all or mostly white like me. Nor were they of similar heights or body types. I think it’s healthy to have flexible dating tastes, and I think I possess this.

Now, for the title. I’ve been examining my various hit tallies and the articles which seem to get the most. And by and large, between now and July 2014, my most popular article is far and away “My Embarrassing 2nd Base Story.” I have utterly no idea how or why this is. It could be the titillating title, or the fact that the story itself is a key example of the hard luck awkward clumsiness that is (or was) my love life. I think this one article makes up about 25-35% of all the hits my entire column here has gotten by itself. It has something like 4,000+ hits and the next closest competition for it isn’t even half that. Now, the point of this blog wasn’t to become popular or scream for attention; in fact I rather like how it remains a rather quiet and intimate thing, where the same folks like and comment in over the months or years and I don’t have to worry about floods of people clogging the comments. I am just fascinated, almost on a scientific level, quite why that post over all others is the clear reader favorite. There are ones where I poured my heart out a bit more than that one, or I thought were riskier or had more substance. But, the people like what they like. Sex sells, and that’s perhaps the closest I ever got to it.

Anyway, this was a story which hit the Internet around November-December 2018. Apparently once or twice a year there is this real life thing called “Sex Island.” It sounds shady as hell, and is believed to be held off the coast of Columbia — that bastion of legality. The gist is that it is somewhat secretive and “guests” who manage to track it down and pay about $6,000 spend a weekend on a Caribbean island filled with drugs and prostitutes. The UK paper The Sun broke the story in 2017, and more reports came in a few months ago. There have been efforts to crack down on this and arrest the organizers and/or the drugged out horny johns, but at last word there was a New Year’s Eve 2018 shindig.

So how did I stumble upon such a raunchy story? I stumbled upon a related story where a 16 year old “won” a ticket to this event when he “borrowed” his father’s credit card and entered the event. He went on to lose his virginity to a prostitute there, who he wants to marry. I usually keep abreast of stories involving people in a similar boat to me, although a 16 year old is hardly what I would call an “older male virgin.” Even I didn’t start to freak out about it until I hit 19-20.

I bring this up since it made me think about my own “evolvingstance on the notion of employing a sex worker to finally make a man of me and end my shame. When I started this blog, I was firmly in the camp of while it is tempting, it would cause more harm than good. And to a degree I still thing this. While it would allow me to physically have sex with someone I was at least physically attracted to, it wouldn’t teach me anything about how to relate to women, socialize, or seduce. And as much angst as I have about having to hide the fact that I am an older virgin to any potential woman I was to date — at least short term — the stigma against sex workers is far worse. Revealing my inexperience, or even that unspoken fetish (which I consider more shameful) is bad enough; but few women would want to know they were dating someone who’d slept with a sex worker.

Now, I have been told many times that women don’t view dating as a job interview and typically don’t ask about previous lovers. While I don’t disagree, I have seen enough people casually interact and mention previous lovers and/or exes enough to know that it would seem weird before long for a woman to date a man who never brings it up if he is beyond a certain age. A man my age (in my mid-late 30’s) who never mentions an ex-wife, a former girlfriend, or any sort of previous activity with a previous lover when compared to the average woman (who usually references an ex or at least some previous encounter or her tastes therein if she gets relaxed enough in a prolonged date conversation) may seem odd. It may even come off as being “standoff-ish” or “distant.” Of course if confronted about that I could coyly lie and say, “I don’t kiss and tell,” but that’s only technically true. Hell, many men a decade or so younger than me already have kids they share visitation with.

But now that I have experienced the near end of my life financially, and the specter of being homeless became very real, there’s emerged a sort of lack of care about other things. One of them is some of the stigmas that I used to fret about. By this point it is abundantly obvious that without either a dramatic stroke of luck or outside intervention, I will never have sex. Now, that in and of itself isn’t such a bad thing to live with anymore; if my recent eviction and unemployment have done anything, it’s remind me of how trivial my love life can seem to be in the grander scheme. I also had that brief encounter with someone online recently where I learned that it felt nice to be flattered, even in a totally artificial situation where nothing was “real.” It felt nice to imagine a woman somewhere was “into” me or at least recognized something about me, like my imagination. It was nice to see the words, out of context, even for a moment.

But much like my fascination about a particular blog entry’s performance, there is a part of me still curious about what sex would be like. What it would be like for a woman to at least pretend to like me for a little while, and tell me what I wanted to hear? It would be nicer if it was a “genuine” situation, but on the other hand, if it were, I am likely to nitpick and over-analyze it to death. Out in the wild if a woman I am interested in actually felt the same way about me, my immediate reaction isn’t “Yay,” it is “Why!?” There’s none of that with a sex worker; I know it is fake and all about the money. I can accept that an attractive woman wouldn’t be anywhere near me without me paying for it; it makes sense in my mind. But an otherwise unattached woman who I was into actually choosing me over any other man, anywhere? That’s unfathomable. I could find better for her than me just by spinning a bottle and directing her towards whatever man it pointed to.

And honestly, there isn’t a vast degree of difference between a consenting sexual encounter with a sex worker in an area where it is legal (like Las Vegas) and “hooking up” with some random woman at a keg party whose name is forgotten. The only difference is the amount of money changing hands, the context, and the social stigma. Trolling for “randos” in a bar is fine, but paying for it is sleazy. While I wouldn’t gain any emotional or social experience, I would gain at least a basic familiarity with a woman’s body and what I did or didn’t like in terms of sex. Some of the edge would be off. Any random date wouldn’t have to be making up for some three decades of futility in quite the same way anymore.

The wildness of a “Sex Island” sounds like something out of a sleazy 1970’s grind-house film, and not something which I would ever seek to entertain. I’m not into drugs, for one, and it sounds like many of the women there are likely all but slaves of cartels. I am not into exploitation or harming women. But it made me think of my own “evolving” opinions on sex work. Maybe it’s only due to my own horny self interest; maybe it’s due to a change of opinion or even desperation. Maybe it is because I probably share more than one thing in common with Holden Caulfield, the lead of Catcher In The Rye (who infamously hires a sex worker, than merely talks with her). Who knows.

There is a part of me that regrets all this introspection. I may have been better off just chugging hardcore into online dating for the last 4-5 years instead and hoping to have gotten more experience out of tenacity. I especially should have let go of a lot of the emotional baggage I carried with me from high school and college regarding my dating woes, and not taken some of them so personally. For better or worse the person I am now is not the same, almost to the point of the irrelevance of comparing performances. Older me would have taken different choices, or not let certain things eat at me so long. But on the other hand, I think I have done a lot to let go of some of those woes, and figure out where I need to go and what I need to fix within. I would like very much to make some genuine connections, have feelings for a woman who actually felt them back to me, and experience genuine love making together. But the realist in me is realizing that I may never get that chance, or if I do, I may only have one shot at it because I am unlikely to have another at my age. So I have to keep all options on the table.

Aside for sex islands. That can be the realm of pop singers or 16 year olds.


Dateless-Man vs. 2018

I was sent down to Earth to show you a reason why you should live, but I can’t think of one darn reason. — “Married with Children,” 1989, “It’s a Bundyful Life, Part 2”

This has been an absolutely terrible, awful, no good, completely rotten year.

There’s really no way to sugar coat it, nor a reason why I would. I’ve been doing these annual round ups for the last 4 years and without any doubt this was the worst year I’ve had while running the blog. I’d argue that my emotional angst regarding my lack of a love life specifically was at its peak in 2014-2015. Last year, I reached a weird sort of Zen. Yet as I’d noted in my “vs. Life” entry, hindsight usually leads to me realizing that as miserable as I was and as bad as things seemed, there is always worse. I never hit rock bottom. Every time I feel I have experienced the worst my life has to offer, in comes another horror to correct me.

To recap, my mother and I have been engaged in an eviction proceeding set against us by our slumlord of a landlord since May. While I didn’t really want to bog down this blog with a topic which, theoretically, has nothing to do with my yearns for a love life or reflection on past or current failures with women, ultimately it became hard to ignore. It’s hard to land a date, after all, if I am homeless. In addition to this, the city job I had landed last year axed me at the end of September; barely 3.5 weeks before I would have become a permanent employee and thus gained more union protections. While I had made my errs, it turned out they had a quota and fired many more “transitional” employees from my training class of October 2017 — including one who was damn near perfect in every way. Next week the eviction case that was opened will be dismissed on technical grounds, but nothing will prevent the landlord from opening a new one, beyond his own impatience and irritation with legal costs. I won’t get into specifics, but let’s say the landlord could have a future playing Shylock in Shakespeare’s The Merchant Of Venice. The only difference is that in the play, Shylock loses in court. In real life, big landlord may be delayed, but never denied.

About the only bits of good news is landing a temporary position after being unemployed for only a month and a half. At this stage I am at the end of my 6 week training course, and will be “hitting the floor” so to speak and handling live callers again on a new system and dealing with a different kind of job sometime this week — possibly as soon as Wednesday. While I have worked on the phones for a living via sales and/or customer service since 2011, I haven’t really taken a full live call in about 2 months and fret about being rusty. After all, even pro athletes who miss that much time need to practice and warm up before hitting full stride again.

The company says all the right things about permanent employment. About how they’re growing and can use the new blood. That the job may not end in April or May and for everyone to think of themselves not as temps, but as future permanent employees. Hell, they’ve been surprisingly candid about how badly they need the help to cover the tax season which is coming up. But I’ve heard all this before and after the fix that was in for the city job, I am not getting ahead of myself this time. Even if I get axed in April or May, that’s still a job for 5-6 months, and that’s fine. It’ll allow me to go on unemployment again, and it will look good on my resume — especially the training. My trainers like me and everyone is claiming I am a natural in class, but, again, I have been here before.

About the only shift since the last posting which vaguely relates to the topic is in regards to what I have dubbed “The Kink Panther.” To recap, on another forum which deals with the fetish I admit to having but will never identify, another poster contacted me at pure random and wanted to do text role-plays with me. There’s nothing sexually explicit in them, even if they relate to the fetish heavily. This has been awkward for me not only because it delves into something I have even more of a taboo about than my virginity, but because the women is quite a bit younger — far younger than I would ever dream of pursuing.

Well, it turns out she lied about her age when we first interacted. When we began I all but made her acknowledge being at least 18. That’s the age of consent in my state, and I did not want to be entrapped; I’ve seen To Catch a Predator on TV. Well, while our interactions have become far more limited than they were over the summer, she has admitted to only being 16. I was frank about how uncomfortable that makes me feel, even though our role-plays, again, are not specifically romantic — albeit not for her lack of trying. Ever since the beginning she has been incredibly flirtatious and has sought to blur the lines between our “character interaction” and online interactions. I have always been polite but never fully engaged her on this. And unfortunately, even admitting that I am uncomfortable and don’t want to lead her on or even hint at anything improper has only increased her opinion of me. It’s just my luck; I finally meet someone of the opposite sex who is actually turned on by integrity, and it’s a teenager from Spain. I suppose I could just cut her off cold turkey and never reply again, or specifically say “this is the end,” but considering we barely interact more than once every 1-3 weeks anymore, I haven’t. Again, nothing about our role plays is sexually suggestive; it’s only the specifics of the fetish which even hint at that. It’s like if the fetish was about gloves and our role-plays were about two characters whose interactions and adventures always involve gloves a lot. And no, gloves are not my fetish.

I can say from this experience how some men seem to genuinely seek out teenagers. The lack of inexperience combined by a teen’s desire to be adventurous makes it easy to be seen as more than you are. I’ve done nothing to “lead her on” beyond display an imagination, integrity, and some romance-neutral compliments. The golden rule for dating is that if a man doesn’t want to seem weird, he shouldn’t date anyone younger than “half his age plus eight,” or so I have read. At this rate that puts it squarely at age 25-27, and ideally I’d prefer someone a bit older. On the other hand, the fact that this is a teenager and therefore no way of making this more than it is could be a good thing to prevent going in too deep. If this was, say, a 30 year old who was this eager, it would be more difficult to not justify getting more personal. At least this way I know there is a wall where I will stop and go no further in our interactions. No lines getting blurred now.

If 2018 has taught me anything, it is that there are scarier things than being alone, and being an older male virgin. I’d rather die a virgin than become homeless. But I didn’t need this lesson again; I’d learned it before I even started this blog. My life has been full of hardships and tragedy, especially after I graduated college, and especially after my grandmother died in 2010. I didn’t need a bigger, badder, and more dangerous sequel version of learning about perspective. And I suppose that considering there are homeless dudes who date — “couch surfing musician” and “starving artist” are boyfriend tropes for a reason — I don’t feel comfortable even thinking about pursuing it when my own situation feels so tenuous. There are men out there who are users, who get their hooks into someone — often a woman — and exploit her for financial gain. I am not one of these men and I don’t even want to accidentally be mistaken for one.

In a way it has helped burn through a lot of the fear of dating and rejection. “I’ve faced housing court, sweetheart; you think I care if you think I’m a geek anymore?” Unfortunately, I doubt when, or if, I will ever get another chance. I am tired of living han to mouth, and tired of all the misery. For once, I would genuinely like a “happy” new year.

Dateless-Man vs. A Life Not Lived

After that previous post, I bet those who follow this blog certainly want an update! I certainly want one.

The truth of the matter is, not much has changed. For every step of progress, I face two of regression. It doesn’t seem to matter whether that’s in regards to my romantic pursuits, my professional life, or just life in general. And to be honest, not much about whether or not my life as I know it will officially and legally be over until early December, which is the next time my mother and I face off against the landlord of doom, and a judge, in housing court. I don’t know how it is in other states or countries, but where I am in New York, the housing court is essentially an enforcement arm of the landlords. If your landlord is small — say, in charge of a 1-4 family building or so — a tenant may have a fair chance. But if the landlord — either individually or as part of a partnership, corporation, or LLC — is in charge of one massive multi-million dollar apartment complex, if not several, then the courts basically act as a legalized minion. A century ago, if our landlord wanted to repel tenants, he or she would have to dirty their hands by going to seedy areas and hiring actual minions to drag them out physically — perhaps even pay some cops in bags of cash. Nowadays, they merely have to attain an attorney and have the courts (and ultimately, a marshal) do it for them in legal terms. Usually the best a tenant can do is delay the inevitable, which is what’s happened so far.

The good news is after being unemployed for roughly 90 days, I have gotten a new job. It’s a temp job which may last until April or May 2019 at best. However, it is with a very long term and notable firm in my neighborhood which, ironically, has ties to the city job which just fired me. If they are impressed enough by me, a permanent position beyond the spring may be possible. But, I’ve heard all this before; at this point I’ll gladly take a temp gig. The pay is less than what I had before, but without union dues, my actual take home will be comparable. To boot, the commute is a lot shorter — I could actually walk it if I had enough time to walk 2-3 miles in the morning. It’s not much farther than a place where I used to work in 2011 — which, ironically, was the last time I was unemployed. It’s another telephone gig, since that’s where my niche has been for the last 7 years. My degree may have the words “social work” on it, but in many ways that feels like a distant memory, and another life. I was last involved in that industry a decade ago, and only for roughly 8.5 months — at least professionally.

I also ran into a co-worker from the city job I was axed from at this new gig! I was actually surprised to see him, since he was far better at the city job than I was. He went into it with experience, and he didn’t have the absences or latenesses (or as many failed calls) as I had. As crushing as it was for me to be fired roughly 3.5 weeks before I finished my probationary period, my co-worker had been fired a mere 10 days before he would have hit it. He told me that our mutual co-worker and pal, a woman I dubbed “Dinah” since I did have a crush on her, had been axed not long after I had been. It seems like that city agency certainly has a kill quota, and performance doesn’t seem to matter. With a steady stream of fresh employees coming in, in addition to part time college students filling some gaps, they’re under little obligation to keep most new hires longer than they have to. Their agency office literally doesn’t have the space — either in work desks or lockers — to keep everyone they hire. The union gets their dues either way, and they don’t lift a finger to prevent a worker from getting axed before they last 12 months.

In the short term, this new job seems nice. It’s 6 weeks of training before we all hit the phones sometime in January. But, to be frank, most jobs are nice at the start. It’s only a few weeks or months in where the demons come out. I’ll have to miss a day due to housing court, which isn’t good.

And there is where the two steps back comes in. Neither me, my lawyer, my mother, or her guardian ad litem have come to terms with the landlord. He wants to offer a buyout, but it is a pittance and not enough to even last longer than 1-2 years elsewhere. He’s since lowered it since November began, for little reason other than a whim, or to stall us. I’ve spoken to him personally, as he’s tried to pressure me directly. He’s not much older than me, and may even be younger. He is an arrogant, impatient person who has been groomed and handed this position. He is passive aggressive and acts like he has little control over anything, while being shrewdly uncompromising the next. Now, I have dealt with a deadbeat father, a vicious aunt, and bullies many times in my life. But without a doubt this landlord is the person who has done my mother and I the most harm in our lives. From the shoddy conditions of our apartment (black mold, pipes that don’t work, crumbling ceilings, etc.) to the eviction, there is no one I hate more. And this is something different for me. It has been a long time since I had deep and passionate hatred for a single human being. The last time I did, it was 7th grade and I was a child — barely a teenager. Now I am an adult, and the stakes are much higher.

Regardless, it is difficult for me to land jobs, or keep jobs, when I never know if I will be homeless any given month, or have to miss a day every 30-90 days due to housing court. For all I know I could have survived my previous job without the stress of battling this since May. My life feels frozen in slow motion in the midst of a deep fall. I can see the bottom, but I can’t reach it, nor can I reach a handhold or anything to save myself. At this point I don’t even care if I hit bottom anymore, it’s the limbo that is eating at me.

It is during this state of impending doom that I rediscovered something which had been in my room for over 15 years. To back things up, when I was in elementary school, my first “puppy love” crush was in regards to a girl dubbed “Cynthia.” She was the subject of my third ever blog entry, dated July 12th, 2014. My crush on her was an open secret by 2nd grade, and things hit the skids by 4th grade in their usual unrequited and deflating manner — she’d essentially pretended to “like” me on a dare, and felt bad about it. I don’t bring thus up to drag on her; it wasn’t a nice thing to do and it did certainly effect me, but we were all kids. Kids aren’t perfect. Anyway, I rediscovered a Valentine from this era.

It was a cheap Chip N’ Dale Rescue Rangers Valentine’s card. But not a full card; more like a printed index card which could be had at a price of perhaps 30-something for a few dollars. This would have been around 1991-1992, when the show was in syndication as part of “the Disney Afternoon.” There was nothing written on it, and the message on the front simply had one of the characters — Chip, the one who dressed like Indiana Jones — leaning on a heart which said something akin to “rescue my heart” amid a yellow background. Nothing was written on the back. I remember on Valentine’s Day in the private Catholic school, the kids would hand these cards back and forth to each other. It wasn’t quite obligatory, but it was routine.


For what it was, it was simple, innocent, and commercial. Yet at some point I’d kept it. To date it was the first, and only, Valentine I had ever gotten from someone who wasn’t a relative. I imagine as a child it was very important to me. I’d stumbled upon it before; I had kept it atop a bookcase, near a harmonica I’d never learned how to play properly. But I never had the heart to throw it out, at least not as a pre-teen, or a teenager, or a college grad.

Coming across it now made me wonder about what sort of life I could have had, had I simply…let some things go. Sure, had Cynthia crushed on me for real and I had a first kiss before junior high, that would have been cool. But it may have been better had I not taken some of my defeats with the opposite sex as personally as I had. At the time they seemed like life altering events. Yet now as I face a real life altering event like homelessness, unemployment, and/or the death of my mother (who is in poor health), these sorts of things seem utterly trivial. What if I had the ability to shrug off some of that pain and keep chugging along? Especially by college, which was fertile ground without much of the baggage of my past that junior high and high school had. What if I capitalized on the one or two flickering chances I had, without any fear? What sort of man would I have become, had I been able to do that? Or been able to land a relationship? Would I have been more confident? Enough that I could have gotten better jobs sooner, and escaped this sort of fate? Or at least had better memories of pleasurable and happy times beyond childhood as I face the end of it all?

So many of the feelings and emotions that I felt regarding women and the opposite sex come from events at least a decade old, if not older, by now. The person I was then is hardly the person I am now. I hadn’t suffered as much, gone through as much turmoil. I hadn’t lived through unemployment, taking care of and then losing my grandmother, the added stress of my own mother’s declining health, and stress regarding my hovel of a home. So on the one hand, I have some more maturity and perspective, as well as social skills, that I lacked when I did 90% of my attempts at dating. On the other hand, I have become a more bitter person. My temper, especially over the past year or so, has gotten worse and harder to maintain. I don’t measure it often, but I likely have high blood pressure. I have have realized now that I am in my later 30’s that some people who I thought were “mean” as a kid weren’t that way because they were evil, or born that way, but because a cruel and unpleasant life had made them that way, like a tormented animal. I’m good at hiding it beyond a personable sense of humor and perhaps an inner goodness, but that cynicism is there below the surface. I trust in nothing and no one, and any time I feel I have nothing left to lose…I usually am in risk of losing more. And on the rare times that I gain something, all that gives me is something more to lose. Which I inevitably will.

To stick with the theme of a TV show, I feel that I am facing a finale. The question is I don’t know whether it is the season finale of my life, or the series finale. There’s a notable speech in 2006’s Rocky Balboa, which seems apt:

The world ain’t all sunshine and rainbows. It’s a very mean and nasty place and I don’t care how tough you are it will beat you to your knees and keep you there permanently if you let it. You, me, or nobody is gonna hit as hard as life. But it ain’t about how hard you hit. It’s about how hard you can get hit and keep moving forward. How much you can take and keep moving forward. That’s how winning is done!

It seems like all I have ever done is take the hits. Moving forward is all I know, whether deliberately or because I stagger that way in a punch drunk haze. But after a decade or two of crippling blows, I can feel my vision finally starting to blur. My knees becoming wobbly. The mat ever so close. And the irony is, I don’t even mind it anymore. I am prepared to accept that my life has come to an end. I am prepared to take that final blow and be left on the mat for the count. To finally leave the damn ring and be through with my punishment. I have no more illusions of winning the match, or a round, or even scoring a hit anymore. Any time I do the beating gets worse than it ever was before. I just want to leave the damn ring. I just want it to be over. Whether it means the ref calls it for a technicality or it ends in a TKO, I don’t care anymore. The endless limbo is driving me crazy.

And to think it all started so innocently with postcards of hearts and cartoon anthropomorphic rodents. Not even in some of my nightmares did I imagine this. I battled and went through so much, only for it to end here. Or in a few weeks, technically. Until then, it’s business as usual, a day at a time, a week at a time. Keep it moving, keep hustling as the kids say now.

Until the last hammer blow finally comes. And when it does, it’s about damn time.

Thanksgiving was alright. My mother and I weren’t feeling very thankful, but we had a nice take out dinner. Beyond November, I have no idea what will come, or how much longer this blog will last. Hopefully 2019 brings something better. I certainly would love to focus once again on those girls that didn’t like me or on my virginity. They seem so trivial now. Especially as I near what was my last chance.

Happy Cyber Monday, everyone! And thanks for reading, as always.

Dateless-Man vs. The End Of the World (as I know it)

It may be the title to a catchy song by R.E.M., but I don’t feel fine.

It seems like every year that I have put this blog together tends to have a theme. 2014-2015 was mostly spent on laying out all of my notable experiences with or about women. This was done in part to get them into another medium besides memory, and also to analyze them. Even to present them as evidence as to why my romantic quest was hopeless and doomed from the start. In 2017, the theme was definitely about a sense of Zen. Well, if 2018 has a theme, it is anxiety and genuinely “real” worries and struggles that make the topic of this blog seem moot. I dislike typing about topics which don’t technically involve my love life or romantically themed musings, but it’s hard not to when it is something which effects everything in my life, including that. I touched upon it in “Dateless-Man vs. Life,” and suffice it to say, everything since has caved in.

Remember how I got that city job in October last year and kept fretting that I wouldn’t last past my year long probationary period? I mentioned in nearly article since how I was amazed I made it that far and could feel the ax fall at any time? Just weeks after my last article in September, it happened. I was only 3.5 weeks away from passing probation. I was late a few times and there were a few odds and ends I didn’t do perfectly, but there was no ONE reason why I was canned. Nor was there any warning. It was just another typical Friday, and my supervisor asks me to pause out for a moment. Nothing unusual, until she says the floor manager wants to see me. This only happens if there is a major technology problem, someone complained about me personally, or some other serious matter. I asked if I was in trouble; she said she didn’t know. Said floor manager then said I suddenly had a “meeting” scheduled in a room typically used to hand out checks on payday. A part of me wondered if it was something good, like an orientation thing since I was on month 11 of 12. But my gut knew it was bad, and I was right.

At this job, the mass firing of probationary employees once they hit months 9 to 11 is fairly routine. They literally hire more people than they have work space or locker room space for. There will always be a steady stream of newbies to replenish the ranks. And not even the union cares because either way, they get dues. On my own team I saw two other employees “vanish” once they hit months 9-10, and one of them took every overtime shift possible. For the sake of maintaining “morale,” nobody is told when someone is axed. After the hammer fell, the floor manager told me “not to make a scene” as I went back to my desk to shut things down and get my stuff. Looking back, I regret not shouting it from the rafters. What were they going to do? Fire me more? If they badmouthed me to future employers, that’s lawsuit territory.

To say it was a blow was an understatement. This was the first job I had in a decade which had any kind of figure. And at my age, it felt like my last chance. And now it was gone. I cleared some odds and ends afterward, and then spent about an hour or two at a public park just laying on a bench. It was a peaceful autumn day, amid the pigeons, trees, and at least one very large spider. If I could have willed myself to die in that moment, I’d have had no regrets. Unfortunately, dying isn’t that easy if you actually want to. I know. I’ve been depressed many times before, and suicide is something I have extensively researched. My dilemma is doing it in a way which is relatively painless without access to firearms or hospital grade drugs.

On top of this, my housing situation has gone to critical mass. As mentioned before, my slumlord of a landlord has been trying to evict my mother and I from our “new age tenement” apartment since May. My apartment features such massive violations such as plumbing that doesn’t work, a non-flushing toilet, black mold for 5-10 years, cracks all throughout the walls and ceiling, and spotty wire-work. But my mother and I have too many belongings, so it’s considered “hording” and grounds for eviction. But the real motivation is that my mother and I have been there long enough that our apartment is “rent controlled,” which means it is way below current rates. And as typical in New York and elsewhere, landlords are greedy bastards who look for any and every excuse to kick out people with low rent — legal or otherwise. Every day at work 1-3 people would call me with similar problems. One old woman lamented to me, “I never killed anyone, I don’t steal, what did I do to deserve this?” It almost broke my heart. But now here we were.

We have been given a devil’s bargain. Accept a buyout to move, with a chunk of money which at best might pay for rent elsewhere for 1-2 years, or possibly be evicted later in the year. Even if we threw out everything, the repairs are so severe that the entire apartment would likely need to be gutted and rebuilt board by board — and the landlord has no intention of paying for any storage or hotels, or being reasonable on deadlines. All of this has effected my already ill mother’s health (and frankly, sanity) even further, and she wants out. Every attempt at legal or agency health has failed, and some would say we’re lucky to have even gotten this far.

So, very likely before December, I will be out of the only home I have ever known. Our options elsewhere are slim and mysterious. My mother has family in California, and a pal in Florida. She has an eye on property in Pennsylvania. All three of those states have an equal if not higher cost of living than where we are now, and similar rents, with lower minimum wages. Florida still has the federal wage, which stands at $7.25 an hour (which has not kept up with inflation since 1968). All of those would require learning how to drive, and then still somehow finding a vehicle. On top of being in an unfamiliar city, state, town, and needing to obtain new ID and everything.

We even discussed splitting the buyout and going separate ways. It is an option, although a part of me does not want to abandon my mother. Everyone else has, and she is not well. I would worry about how she is doing. Most of her options involve relatives who don’t give a damn about her, or pals who are either older and/or in worse health than she is. In theory if I wanted to stick to the apartment no matter what, I could stall things. But then it wouldn’t be the landlord making her life miserable, it would be me. And I can’t do that to her.

The next 45-30 days are likely going to define my life, which is already in a downward spiral. It will be double or nothing, and every time I rolled those odds, I wound up with nothing. I was born with nothing, and I still have most of it. That’s an old joke, anyway.

The last time things looked this economically bleak was in December 2010 to about fall 2011. I was without a job, and unemployment ran out. Grandmother was dead, and her meager resources were no longer available. I didn’t get a job until July, and even then it was part time at that time. My bank account went down to about $12. As of now, it stands at $50. And I will admit, in 2011, I was often depressed and contemplated suicide many times. I can’t remember how many times I was tempted to leap in front of a train coming home from a job interview I already knew was going nowhere. And there were hot agonizing emotions about it. But then again, at that time I was in my late 20’s. I still felt entitled to things. I still thought I had a chance.

Now things are different. I am older and wiser. I see life as a burden, something I have to endure, not experience. My mother and I have lived through some rough times, and every time we survive one round, years down the road when we face worse, we all but reminisce about the past. That is what has happened now. We make jokes about the miserable times of 2016 or 2011 or 2010 or 2009 because they still were better than now. And I genuinely don’t want to see what comes next. I don’t want to see what comes next that is so bad, that sometime in 2019 or 2020 we crack wise and go, “Yeah, remember when we were in that crumbling moldy apartment being evicted and scared for our lives? Weren’t those the days?” I don’t want to go there. Life itself is not worth it enough for me to want to endure this.

My story does not have a happy ending, and never has. It has endured for two reasons; my masochistic sense that eventually the odds will tilt in my favor if only because no streak endures forever, and because I have been too cowardly or lacked the opportunity to end my own life. This time I have shed no tears. There is no hot emotion beyond occasional bursts of anger or frustration. I am now older than a slew of historical figures, from Jesus Christ to Jimmy Hendrix. I am old enough that nobody under the age of 65 would claim I was in “the prime of my life.” If this was the prime, then it’s time to cash out. I am just spinning my wheels and waiting for the end. And I feel it coming faster now. I honestly didn’t expect or want my sickly mother to still be alive for it, but then again, not one moment of my life has been what I expected.

It’s probably for the best that I never had a romantic relationship. I’m a basket case and eventually I would have made a woman miserable, needing to be reassured every day. It would have been nice to experience, but so would have no end of experiences. I suppose in theory, if we did move to another state, in theory this is one area where I might see an improvement. Outside of NY, people get nicer, so I hear. And suddenly I would be the interesting out-of-towner with the different accent. At least two people who reply here have suggested I move in part for this reason, so who knows. But honestly, dying a virgin is the least of my worries now.

Every time I feel I don’t have anything left to lose, I realize I did. About all that’s left is my mother, and my health. I fully expect one or both to go before I realize it. I am tired of losing. And I am tired of people who blame it all on attitude or a lack of skill or a lack of will. I have endured and survived without a father, through over 30+ years of abject poverty, through watching the only parent I have ever known die by inches for almost 20 of those years, through one demeaning job after the next, and through assuming blame thrown at me by either my mother, customers, clients, or teachers for things I never did and had nothing to do with. I left a dead end job I was very comfortable in for a better life, and just as I feared, it all turned the poison when I got close. There is willpower, and then there is stubbornness. There is no winning this match; I have already lost by TKO about 15 rounds ago. All I want is to leave the ring without being slapped down and drug back in for more torment. I just want to leave it behind me. Maybe that is why I always had a sense of humor and some inborn skill at devil-may-care, spontaneous comedy. I wanted to wrangle some enjoyment and happiness at my own miserable cesspool of a life. I want to die with a smirk and wisecrack on my face. I want to meet the Grim Reaper and tell him his ass looks pretty bony, he should work out more. Then I’d ask what kept him, since I’d been ready for about a decade or so. It’s like another song, this one from Blue Oyster Cult — I don’t fear the Reaper.

Whatever contacts or opportunities I have are in New York, and even those would be short term. Outside of that I have nothing, and no one. Just another bum who couldn’t cut it in the Big Apple who was flushed down somewhere else. I’ve seen the bottom of one city, I don’t want to see the bottom of more. Nobody who has to start over past 35 ever gets anywhere near anything decent. Not without some miraculous skill or luck, neither of which I have so far. And above it all I failed to bring my mother out of poverty, either. I failed her as much as I failed myself, if not more. I was always the person who was told had potential, but never was able to make it work. So what good was it?

I may still be where I am by next month, but after that, who knows? This isn’t good-bye, because that would mean I know it is good-bye. Maybe things will work out and I can regale everyone with angst about trying OkCupid in a new area or seeing if the dive bar has any women dumb enough to fall for a guy who sounds like a New York cop. But more than likely things will cave in and I may not post for a while. Life’s supposed to be about the awe and challenge of not knowing, right?

If you’re someone who was like me, an older male virgin looking for a shared voice in the wilderness, I am sorry I could not become a success story for you. I am sorry I could not find a way to escape my own pit and deliver what wisdom I discovered to you. I am sorry I couldn’t then package said wisdom in a few hundred well pitched words and charge you $9.99 for it or something similar for “personal coaching.” But maybe in my own way, I can fulfill another need. There is a lot of Pollyanna, saccharine baloney out there in the realm of dating advice for older virgins, with no one willing or brave enough to say or confirm those worst fears. That sometimes life doesn’t get better. That sometimes all you are and all you do won’t be enough, that you can still fail every time and wind up in the gutter. That such a fear is not as illogical or impossible as the Confidence Gurus (TM) will insist. And while I suppose it is worth it to try, always try knowing that failure is an option, whether you want it to be or not. Life breaks all of us in time, some sooner and worse than others. One day it will come for you, when you least expect it, in a form you never prepared for. I thought I’d already been properly broken, but every time a boot came to stomp the shards further when I wasn’t looking.

So I guess despite my lamentation near the start of this blog in 2014, my best role is that of Jacob Marley — someone to avoid becoming.

And I am still tired of being Jacob Marley.

The Kink Panther Leaves amid Co-Worker Rumblings

It’s nearly the end of the month so it’s time for another blog post. The most pressing update is my housing situation. The saga, or sham, of housing court continues. It has been adjourned again to mid October. It feels like waiting for my economic life to come to an end in slow motion. And until then there is little I can do but take work one day at a time. I’ve had plenty of”real life”things take my focus away from dating or my own non-existent, premature, failure of a love life, but this takes the cake. I genuinely don’t want to see what gets worse than possibly becoming homeless. I’m on month 11 out of 12 for probation, and still expecting to be axed any day.

But until that happens, thanks to sublimation I can comment on other things more in line with the stated purpose of this blog. And both of these updates and segments are bits which might be too short to make their own proper installments individually, but together may produce a proper length. I don’t have a text minimum or anything, I just like expressing myself with the proper wordage. “New month, not dead yet,” doesn’t quite fill up a screen too well.

The first update stems directly from last month, which maintains a sense of flow. While I haven’t planned the order or subjects of posts so often since I ran out of meaty past memories a few years ago, I do like when the subjects fit together from month to month. After all, I imagine myself a writer. Back in August I reported on a slightly significant development in terms of the subjects of this blog. To recap, I’d stumbled across a younger woman online whose fetish taste happened to match up with mine, and we’d spent the summer doing text RP sessions via instant messages. And no, I am still not going to reveal it openly here. Anyway, I went at it from all angles, mingling my fascination with ANY positive experience with a woman in any medium with concerns over her age (she was in college) as well as pondering if maybe I divide segments of myself too much out of shyness and shame.

Well, like many things in life, it’s ended anti-climatically. The two of us would IM several times a day, or at least daily, from June thru the top of August. Yet for the past month or so as summer has waned into fall, she fell off. It wasn’t just our “roleplaying,” it was also our chatter between each other on the forum where she’d first reached out to me. By about mid August I was lucky to get 2-3 exchanges in a week. And now it’s been nothing since about Sept. 9th. The Kink Panther may have been stirred, but now it is time to slumber once more.

I’m actually not terribly disappointed about this. It’d be creepy if I was, since all this was was a little text role-play online — “CHOOSE YOUR OWN ADVENTURE” with a partner where nothing got beyond PG. Nor did I especially want it to. As I said, while it was genuinely flattering and ego boosting to have a woman compliment me or call me “awesome” or flirt with me, even via text, the age gap was a bit distressing for me. It was nothing illegal — I all but demanded she acknowledge being over 18 before any of this started — but still beyond any age gap I was really comfortable with. While we both indulged our fetishes in our shared fan fiction, there were lines I wouldn’t cross. The distance between us was another factor — she lives in Madrid, Spain — but the age was the biggest factor. I felt like I was straddling the line of what was acceptable for someone in my position to do considering my age and morality. And all of this was over wordplay which was less risque than the average romance paperback at most chain pharmacies!

It’s possible (even likely) that she was investing more emotion in this than I was, and lost interest. I return compliments every time, but it never got as flirty as I think she wanted it to. She often blurred the line between “her” and “her character” more than I was willing to. Again, on my end this was another symptom to her being much younger. I did not want to take advantage, or lead her on, or give her illusions I had no intention of fulfilling, even in as small an interaction as we had going. Were she, say, at least 25-26 maybe things would have gotten more complicated. I may have pushed the envelope more. But younger than that and I feel like a vampire, or Dorian Grey.

It’s possible she lost interest because, well…she’s at that age where that happens. It’s possible school season’s kicked up and she has far less spare time. Maybe she was RPing with some other dudes closer to her own age who played the game more to her liking. Or it could be a combination of these things. Regardless, I do consider it a learning experience, and an unexpected bright spot on a summer which has been pretty stressful and terrible overall. I learned that it was possible for a woman to be receptive, even enthusiastic and complimentary, of a part of my sexual identity which I am even more ashamed of than being a virgin in my 30’s. I once again learned what I am willing to do and not do to “scratch my itches,” albeit even in limited forms such as text and shared imagination. I will not exploit ignorance to get pleasure from a woman, at least not comfortably. The disadvantage of a younger woman, especially one in her mid to early 20’s, is she doesn’t have enough life experience to realize what a loser I am. I do. And if I capitalize, then I take responsibility for misleading someone.

Amid all this, I have a somewhat interesting dynamic relating to a co-worker. I haven’t talked about any of my co-workers often, since my last job in 2016. This new city job has produced a new mass of co-workers to have to interact with, but they’re not the same. Most are too “normal,” too focused on career to have much imagination, and too cutthroat to allow any difference or abnormality to emerge without trying to score brownie points gossiping to a supervisor. It gave me a bit of pause to become face to face so many times with that which I have punished myself for being unable to become — a “normal” person. So lacking in passion, understanding, empathy, or anything beyond a spreadsheet and mindless protocol. I may hardly be much of a freak, but next to the norms I may as well wear a gimp mask and dance in a cage.

No, that is not my fetish.

There are also more women at this new job, and the co-workers I got the closest to were the ones who did training with me last October. That makes sense, since the shared environment and experiences were very much like a class. All of us were bundles of nerves, together. And all of us got thrown into the fire of “the real job” at the same time. The one I have probably gotten the closest to is a woman who will now get an alias. How about Dinah? (For those who may be new or haven’t kept up with previous chapters, I use aliases for women that I specifically talk about in my life in which I take the first letter of their first name and come up with an alternate name around that.) I’d noticed her not long into my training, but midway thru it they switched our seating arrangements so we sat together.

The frustrating thing about myself is despite all of my bleating about being an outcast or bad at talking to people, I’m fine so long as romance is off the table. I’ve actually gotten better at it since mid-2011, when I first began my “career” of telephone customer service/telemarketing. I HAD to. I had under $20 in my bank account at the time and no other jobs were happening. Matched with my own natural inclination to use humor and wisecracks to interact with people, and it actually gives off the impression that I am way friendlier and/or socially hip than I am. And since I don’t see the workplace as a dating service, even though I may encounter women who are “my type” at a particular job, I don’t have illusions or delusions about that. As my experience with, say, exploring a fetish under an alias online (as well as my dating angst) shows, I am fine with sublimating and dividing segments of my life. Perhaps too good. Anyway, what this ironically means is that I probably have an easier time revealing my “genuine self” or closer to it to someone with which I am not actively trying to woo.

Dinah didn’t immediately seem like the sort of person who might like my often cynical sense of humor, but she has. But then again, most people do; I say it a lot and it translates horribly here, but in real life it isn’t hard for me to make someone laugh so long as the timing is appropriate and they’re not humorless in general. We often sit near each other on the work floor (since we have to sit as near our supervisor as possible) and even our lockers are pretty close together. Any work dealing with the public, whether by phone or live, means some in between call banter to de-stress and we do that sometimes. And we talk if we run into each other at the end of the day in the locker room (which, obviously, are co-ed with lockers exactly as crummy as high school lockers).

Now, however, we’ve reached that point in my interactions with any woman I get to know for any length of time who may be “my type” where I wonder what is genuine friendliness or interaction and what is a sign she may “like me” in some ways. Usually, from what I have learned from the Internet, TV, and urban legends, it’s some deviance from the routine. There are times when I feel she goes out of her way to get a chance to talk to me, although it’s hardly an everyday thing. During one period when our schedules and seating arrangements resulted in zero contact for about a week or so, I entered the locker room with her there and she said, “I was JUST thinking about you.”

No woman, who wasn’t a relative or teacher, in any circumstance had said anything like that to me in at least a decade, if not ever. I had to stop from either gasping or doing a double take. I am not exaggerating. Positive interactions with women I am even remotely into are more rare than an honest televangelist. “R-Really,” I believe I stammered. “Nothing bad, I hope.” It turned out to just be that we’d been passing ships lately.

The wrinkle of course isn’t just that it is work. Dating at the workplace or among co-workers is often considered forbidden fruit for a variety of reasons. Guilty corporate men fearing lawsuits is one of them. Another is that if things go badly or are misunderstood, at best it can make the workplace awkward and lead to distracting gossip. At worst, it could lead to a complaint to HR or a supervisor. Dating co-workers is considered “expert level dating” for this reason alone, and even many ravenous stud-muffins will draw a line at it. But at my work place in particular the added wrinkle is the element I described earlier; other co-workers or supervisors seemingly eager to complain or issue a write up for even the slightest perception of a rule violation. I don’t fear if I made a move at Dinah and our wires were crossed she’d personally run to make a sexual harassment claim. I fear that any supervisor or random co-worker who gets wind of it would do so. My position is the lowest rung of the totem pole, and a “probie” is lower than even that. And this job never lets me forget it for even one week.

So this keeps me from getting my hopes up or desiring this to change realms from professional to personal. So it, ironically, keeps me at ease talking with her. Because I am a guy who can be myself at work, and a masked virgin here, and a masked fetish explorer elsewhere. But there are times where I wonder if dividing myself, as well as burying things about myself that I dislike, is really the best way to live. Were I younger I would be moaning and groaning at how cruel fate was regarding this situation with Dinah. But as an older adult with perspective I know it’s just one of those things. It is what it is and I am comfortable with where it is and so is she.

So anyway, that’s where I am at in between housing court drudgery. Sink your teeth into that one. And no, that’s not my fetish.

The Kink Panther

It actually is a bit of a shame that this blog, much like my entire life at the moment, is under the specter of homelessness and/or economic despair despite still having my city job (month 9 out of 12 of probation is in the can). Not just because of homelessness being bad, but because I had a genuinely interesting development related to this blog’s topic develop more or less ever since my last installment was posted in July. In fact, in many ways it dovetails with a segment from 2016. It’s always good when this blog has some sense of narrative flow, especially since it is totally unintentional.

Rather than summarize that last installment, I’ll just get to the gist. In addition to being a hapless older male virgin, I also have a sexual fetish. Quite what it is I shall never reveal. Should anyone even guess it, I would deny it or decline to comment. Suffice it to say, it’s nothing illegal and it, like many of my “darkest desires,” is probably tamer than the average prime time TV show. It was something which developed alongside my sexual development during puberty. I likely feel certain degrees of shame around it, and perhaps this helps fuel a lot of my romantic shyness and anxiety. After all, a virgin in his 30’s is weird and bizarre enough; reveal he has a fetish too and suddenly it risks being seen as a creep. “Oh, so that’s why no woman will touch you! You’re a pervert!” I imagine the hordes screaming. It’s bad enough being seen as a potential mass shooter in waiting.

Ever since the Internet became a part of my daily life in college, I’ve sought to dip my toe into exploring it in the usual way I explore things. I use an online alias to keep my identity a mystery, and I separate it from my “everyday” life and identity as much as I can. I’m a man behind a mask, but I wear more than one mask. Perhaps the way I compartmentalize everything in my life is another quirk or problem. My “real friends” are here, my “work associates” are here, my love life is in a box over there, and the fetish trunk is off to the side. Never the twain shall meet, yet they’re all elements of who I am. Maybe it doesn’t get easier to explore or move forward in any one direction when I am already split up in several. Yet on the rare chances there is a risk of overlap, I found it very disconcerting at best, and nerve wracking at worst. The world is complicated, and my life has been a chaotic mix of poverty and tenacity, so I try to inject as much order and purpose as possible. Even where none may be possible.

At any rate, in this other “community” I am one of countless people behind a fake name and an avatar image on a screen. And I interact with people, yet my interactions are far more limited than my efforts here, or over at Doctor Nerdlove’s spare forum. At some point at pure random another user — a much younger woman — has reached out to me in private messages. Quite why she chose me I have no idea, but we got to talking and now we essentially role play our fetishes via instant message texts and shared imagination. It is sort of like CHOOSE YOUR OWN ADVENTURE with a partner.

To say this is a bizarre situation is to put it mildly. Before we began, fearing some sort of set up or misunderstanding, I insisted that she acknowledge being at least 18 or over in text (which I saved). The last thing I wanted to do is stumble into a pedophile’s trap. And while this does revolve around a fetish, none of our actual roleplays themselves are strictly erotic. It isn’t like what used to be known as “cyber,” where two people online basically describe having sex with each other via text. In fact, while if looked at objectively, the fetish would be obvious, the material is little different than a lot of pop fiction which is rated PG or so. It’s content which may check off the fetish boxes for those who share it, but to outsiders is hardly what any would consider pornographic. No mention of genitals, and our “characters” never take off clothes in our “adventures.”

I’ve engaged in message board role playing as part of my daily routine since 2002. Yet much of this until now has been centered around the universes within comic books or anime that I like, or games created by some of my friends. It’s an extension of the tabletop RPG’s my friends and I played in high school (character sheets, dice and all). I’ve interacted with players much younger than me before as part of this, and this hasn’t been a problem for the most part. Yet this is something quite different. Much as people who know me as the Dateless-Man know me first and foremost because of my shameful secret, this is someone who knows me first and foremost because of a shared fetish. It’s the first detail which we knew we had in common, and the rest is extended from that.

Yet because of my own woeful inexperience and my segmenting of aspects of my life, she has become the first woman in my entire life who has interacted with me regarding a topic which at least vaguely sexual. And not just sexual, but a part of my sexual identity which I both acknowledge and consider taboo. In this small, baby step way, I have met someone who approves of and wants to interact with at least one aspect of my romantic self, albeit in text, across vast differences (since she lives in Europe), and in a format which is far tamer than I am making it seem.

Part of this is difficult. Because she is quite a bit younger than I (a college freshman), I am very careful with my responses outside of the roleplay. I do not want to scare her off or appear mean. On the other hand, I do not want to lead her on or make this into more than it is. The other part of this is that she’s quite…enthusiastic about certain things. “Out of character” she flirts and offers compliments (i.e. it isn’t rare for her to call me “handsome” even though she has no idea what I look like). Because I have a vivid imagination and a clever grasp of wordplay (as well as a quick wit, it seems), I have somehow emerged as near the peak of those she has roleplayed this stuff with — at least so she claims. We collaborate a little on the basic premise of whatever roleplay she wants and then I essentially come up with all the details, including character dialogue, virtually on the fly. Somehow she sees this as magic, or above average. She has called me “awesome” many times, for instance. I assume a lot of this is due to her own inexperience compared to my experience. I’ve had years to practice how to write, after all. I’m a college graduate and I have been both role playing online and writing in general a long time. And then she has escalated to the point where, on her own volition, she sent me pictures of herself. They’re standard Facebook style picture, nothing suggestive or anything, but they were still unprompted and I do worry she is maybe making more of this than I want to. So I play a bit of a game where I want to give positive responses while also being vague on details and I wonder if this is better or worse than just going, “Look, I am thirty-[BLANK] years old and while the RP’s are fun it isn’t developing into anything more.”

Yet on the other hand, I know what it is like to be weird and lonely. I suppose by now I should come up with a patented nickname for her, so I’ll go with “Ellie”. From how she describes things, men her age where she is don’t appreciate “geeky” girls. And our forum is one revolving around a fetish, which most people keep under wraps. I’m not the first person she’s RP’d like this before (she’s implied she’s done this with at least two others, whether currently or in the past is unknown). She does blur the line between her “character” and her sometimes, perhaps in the similar way that I go online and only talk about my fretting about being a crusty old virgin as “the Dateless-Man (TM)”. While she teases about meeting up and cosplaying, the distance makes that doubtful. Nor would I engage her if it got to that level. She is simply too young.

This interaction with Ellie reminded me a bit of some of the advice I have been given over the years. More than one person, including one of our regular commentors, suggested I go after younger women rather than ones my age or older more or less for this reason. That their inexperience matched with their current development phase (often still in the “fooling around/exploring stuff for the sake of exploration” age) means they may be more down with stumbling upon an old unicorn like me rather than a woman who is 30+ with a kid and two jobs. Yet to me that feels awkward at best, and taking advantage of naivety at worst, and I do not like to take advantage of people deliberately.

A part of me wonders just how “awesome” Ellie would think I am if she knew I was a 30+ year old virgin who still lived with my mother who was THIS CLOSE to becoming homeless. I only seem clever or sophisticated because I have better text wordplay and imagination than the mostly teenage dudes she’s been used to — go me, I can outwit men half my age (or more). It’s easy to pretend to be suave or charming via the written word; you have all the time in the world to come up with the perfect line, and can look at your own archives in black and white to think about each subsequent response. Whereas the real life experience is far less eloquent or elegant. It’s a conditional and temporary phase, one which she or others in her situation may one day regret doing if things go too far. While I would never, say, search for people this young were I to make a serious go on OkCupid again, it isn’t impossible for me to stumble upon someone age 21 in a bar. The last speed dating event I want to at a comic convention was full of women who were, at best, a day over 21. And while over 18 is over the age of consent, does that entirely mean someone aged 18-21 or so is incapable of offering it? Is it wrong of me to deny someone autonomy if it just sort of happened? Is is wrong to be that “cool older guy” even if I know objectively it’s a phase? Where does the line between taking advantage and capitalizing begin? Sure, ideally I shouldn’t even consider dating anyone under 25-26 under the “half your age plus 8” rule, and even that’s awfully young. Yet am I once again overthinking even theoretical stuff just to stay miserable? If a gal wanted to add “witty older virgin” to her Pokemon badge vest, is it being controlling to insist that I know better?

There are parts of this, while still in the realm of not being pornographic or seductive, that I wonder might end up being good practice or showcase what sort of lover I could be. Being that these are role plays based heavily around a fetish, I have an idea of what she likes (especially since in our planning sessions she’s more or less told me in so many words). There is one aspect or angle that isn’t quite my bag, but I am willing to compromise about in small ways within the shared narrative because I know she likes it. Plus, my years of running less kinky role plays has taught me that it isn’t about being a parasite, but a give and take. A “player” is willing to have more fun and stick around if I give them what they want sometimes, rather than be inflexible or make it all about myself. And adapting to a narrative curve-ball in a session is kind of fun. And when they have fun, I have fun, because it is a shared experience.

Perhaps most importantly was showcasing my ability to compromise in the “fetish sessions” with one instance where I crossed a line. Without knowing it I had written some angle which to Ellie went a little too far. Again, this is nothing pornographic or involves genitalia, but the sort of unique quirks and tropes of our fetish. I stumbled into a bit which wasn’t her bag, completely innocently. Ellie made it very clear this was too far and basically asked me to redo it. And did I get defensive and obstinate? At best I plead my case for one line before capitulating. It’s the overall session which matters, and us being comfortable. Ellie not liking it was enough, and ultimately it was hardly a big deal, especially in the imaginary world of text role playing. Yet I hear in the world of real sex and romance, being able to be flexible and adaptable with shared interests and making a well intended err are good qualities. To me they’re just automatic reflexes.

In another post about temptation from 2015, I wondered how I would react upon hearing certain things. While I have been complimented by women before, even by those I was or could have been romantically interested in, this seems different. Perhaps because Ellie is part of a world which I and many others lock in boxes and don’t share with the world out of fear. Or at least perhaps because I do. The very idea that someone could know this one detail about me and still consider me “awesome” is kind of flattering. It is absolutely rare when I feel that emotion around women, or anything that hinted at something kinky or risque. I usually feel invisible at best and like a freak at worst around women, or situations which even tease with being romantic or kinky.

At least until I remember the reality. This is a young woman who is a world away, who is too young to realize how lame I am, and who I am a different cohort to. Our interactions are fun, but ultimately the sort of online baby steps of exploration that most people in their 20’s or so have long since moved past. Ellie is right on track in her development, while I am akin to a gnome under a bridge that time forgot. I may be a nice gnome, and we may have a good visit for a time, but ultimately this is a fleeting experience. Ellie has the world ahead of her, of which I am a very small part. I don’t mind having been part of a positive experience for someone else, especially a geeky kid who feels peers can’t relate. But on the other hand, I know of the limitations, and that my own development has forever been stunted.

Perhaps something constructive could have been learned from this. Perhaps my failure in online dating in college was not due to me being terrible, but the fact that I barely gave it full gusto, and that my writing skills have had over 11 years to develop. Maybe there is a way to capitalize on this in text, with people my own age. And even if I failed, maybe I would improve over time. But what then? What if I wooed someone with wordplay, only to be “Herp, derp, do you like stuff” in real life due to insecurity? Is it wrong to use my writing skills to project a version of myself that I in no way, shape or form could live up to? What about doing so with my voice? I’ve technically made a living with it via telephone jobs for 7 years. There are chat-lines, although they are not cheap.

This is a fascinating development. For a fleeting moment I have a little positive vibes around an element of myself that I am even shyer about than being a virgin. Such a shame that it has arisen at a time when my own economic instability may make all of this academic. Thanks for reading, everyone.

Dateless-Man vs. Life

July marks the 4th anniversary of this blog. Both I and this space have gone through a lot. I began this journey needing a place to vent a lot of my frustrations, memories, and theories about the opposite sex. It took a while to burn through my history of major interactions with women — not all interactions, but most of the critical ones. A part of me is amazed it took as long as it did, considering I’d only been on three dates in my life and still am flying Virgin Airlines. June went by without a post, because I’ve been busy with life.

Unfortunately, not much of it have been good. I am still working at my new city job, having just passed the 8th month threshold. Only four left until I make it past probation, and therefore my job becomes harder to lose. They already feel like a century, although back in the spring I would have been psyched to make it this far. I hate twisting in the wind, where every mistake or misstep seems like an unforgivable offense. But the worst part of it is that my elderly, disabled mother (and I) are facing eviction from our slumlord. Our tenement apartment building gained a new management company in December 2017, and they officially assumed command in January. This was the 4th management company overseeing the building since 2009 (when the original landlord was murdered). The building is a den of disrepair and health code violations, and has been run by varying batches of mobsters, retired mobsters, and white collar criminals since as far back as I could remember. Such is the state of real estate in New York. Because my mother and I have been in one apartment since 1983 — and won a lawsuit which froze the rent a while — we likely pay among the lowest rent in the building. Furthermore, we’re also the 2nd longest serving tenants there; half the building has barely been there 2 years, by design. So the cross-hairs are on us, and we’re going thru the merry go ’round of housing court and various agencies which never help. Even my union lawyer does slightly more than nothing. Despite never missing rent, and despite living in a hovel which has black mold and where the pipes don’t work, and half the ceilings are cracked or look like they’re about to collapse, the odds of me being homeless around Labor Day, or at best Halloween, is even.

I was technically homeless within the first year of my life; thankfully I don’t recall it. The notion of becoming homeless for the second time in less than 40 years is not only scary, but is pathetic for someone who lives in “the richest nation in the world.” Suffice it to say, my fretting or philosophizing about being a single virgin took lower priority. Not to say that the oncoming catastrophe has made me never think about it at all; it’s simply become “one more thing.” Something to cast aside until times improve, if ever. Yet my enemy remains time itself.

And that got me thinking. There isn’t much to do when you await a meteor to hit me, at least economically. I think to the previous tragedies in my life, or my mother’s life, which resulted in having to cope, or recover, or adapt to a new change, which pushed my love life to the curb. In summer 2016, for example, a knee injury was an obvious example. But that was barely a drop in the bucket. So for my sake and your reading pleasure, I’ll list a few by year. The challenge will be doing so without revealing my age.

1994-1996: My mother’s health was waning, I was taking more responsibility, and her own failing health and sanity led Grandma to spend more time with us. I literally shared a room with her 75% of the time by this stage.

1999: My mother officially and legally becomes handicapped and can no longer work. Money becomes tighter. I have to grow up faster.

2000-2005: My mother becomes a basket case for a bit over some of her own relationships that end badly. I wonder if this effected me? Some of these years include my peak depression years in college.

2005-2008: Grandma’s health declines and America’s botched health care system begins ruining her. Home care attendants don’t cut it anymore, and tending to her becomes my mother’s full time job, and my part time job.

2009-2011: I am unemployed for 2.5 years (and unemployment insurance barely lasted for two). I have been devoting 1-2 days a week of full time duty tending to Grandma (and my own declining mother) from 2008-2010. Grandma dies in the beginning of 2010. Our building has been sold from its original owner (who was murdered) and the shenanigans begin in earnest.

2012: Finally working full time again, yet still broke a lot. Apartment construction took a lot of time. Around this time, mother and I never leave the apartment unoccupied.

2013-2014ish: For an 8 month period, the door breaks and literally won’t lock.

2016: Injure my knee briefly. Work drastically changes, am unsure if I will cut it and plan month to month.

2017: I cut it, but the company folds. Immediately found new company with co-workers and management, yet still unsure how long it will last. I learned that in the industry I was in, a company can go from “normal week, full payroll,” to “everyone’s fired” within a weekend.

2018: Facing eviction. Likely the end of the economic road.

Some of the years are fudgy but you get the point. After all, I don’t review what year the bullying happened. For a large chunk of my life, especially post-puberty, I was reeling from one thing or another. And amid all this I was still trying to have a life, hang with friends, date, do hobbies, etc. But for large chunks of time it took a back seat. It seems unfair to date, for instance, when I am broke. Or spending most of my time on relatives. Or morbidly depressed. Or worried I am about to lose my job any week. Or, in 2018, expecting to be on the street sometime after August.

Now, these sorts of woes are nothing compared to what most people have faced (although in my defense, this list is the Cliff’s Notes of Cliff’s Notes). And there are plenty of people who have dated thru tragedies. War, death, hell, sometimes tragedy is the motivation for a pointless rebound fling. Lord have I considered quitting my job, cashing in unused sick/vacation days, going to Vegas, and becoming a man (and going on a drinking binge) for a week or so. But ultimately that’s only a distraction and won’t solve anything. But I never felt comfortable dating when the background radiation of my life was hardship. And the shame of it is that hardship is all I have ever known. It’s relative, of course. I have never been raped, or suffered a stint in a hospital. I don’t live in a third world country. I imagine most kids in Iraq would consider my life paradise. But that doesn’t negate the fact that for me, it has always felt like my dating woes were more than just my inner lameness, or lack of charisma, or even poor luck. That life itself was organizing against me. That any time I took a step forward, I was knocked five back. I have adapted to more in my time than most of my male friends will ever know, or comprehend. It would have killed them in a week. But there are times I wonder if not all of me made it, if a part of my soul hasn’t come out whole since childhood.

And I wonder if my desire to write is born out of nothing more than an attempt to be remembered when life finally knocks me back hard enough that I fail to get up. So that whatever wisp of a life I had or didn’t have didn’t just vanish altogether. So, to quote the best line from Blade Runner,

“all those moments won’t be lost in time. Like tears in rain.”

I was the Dateless-Man, and I was here. Hardly anyone noticed, but I was here. And for now, I am still here.

The annoying thing is, before this eviction mess began, I actually had some interesting anecdotes to add to the blog! I ran into an old friend, however briefly, who invites a topic about dating mothers. And I have a development relating to the fetish I reveal exists but never talk about! And that long awaited lecture about a film which meant a lot to me at a terrible time of my life. I hope to share all of these with everyone reading the blog soon.

Assuming I am not writing it from under an overpass.