A baby step back to the future

Believe it or not I do try to average at least two blog posts a month (with occasional spurts of more), but it seems that I did miss that schedule again. The reason has been a mixture of my work schedule (both my day and night job and hobbies) as well as a general sense of malaise. I think such a sense has been obvious all summer, now that I look back. Two out of my last three posts have been dealing with my angst of being an older male virgin; after all, I am even more “over 30” this year than I was when I began this long term recount of my dating failures. As I have stated before, I feel myself at the center of a crossroads between giving up on dating forever (or at least the near and incoming future) versus making one last desperate push based on absolutely nothing logical. Usually the months between March and October are the months where my general sense of depression decreases. I am hardly depressed, but I simply feel a sense of being adrift in a lonely ocean and wondering whether it is worth it to strain my arms in futility trying to pick a direction in this matter or to simply continue to allow the tide to take me.

I know I am not an ideal lover or date for most women around me. I know that I have very little to offer either physically or in terms of charisma. I know that I have no end of esteem and emotional issues, as well as plenty of real financial and even family worries to juggle as well. My mother’s long term health is rarely good, after all. On the other hand, I am not getting any younger, and as difficult as all this is now, it will be even harder when I am “over 40” or beyond. There are no end of men going through just as much as I am or worse who don’t give a damn about dumping their problems or issues on women in their quests to get laid; why must I be the lone hold out in the universe? Sure, I may have integrity, but that doesn’t keep you content at night for long. My ideal to quash the very feelings of loneliness doesn’t seem to be entirely and permanently possible without some outside substance or horrible brain injury – neither of which I desire.

The truth is that I have been in the middle of a period of “giving up trying” in terms of romance for at least six years. My 20’s faded away and now I am where I am now. And the more I mull over options and worst case outcomes, the more time I may be losing. There is a part of me that wants this, that wants all of this stress and self mourning to be over. But there’s this other part that still wants to try and succeed at this, despite the mountain of evidence I have complied in the installments below which state fairly clearly that I am not cut out for this. I’ve had few genuine opportunities at romance. What opportunities I had I botched so spectacularly that it took me years to realize it. Yet despite all that hindsight, I likely would screw up again if I went at it again. There’s no reason why I should believe otherwise. If there is one lesson I have learned in life, it that regardless of age or setting, no woman I have ever had even faint attraction towards has ever been interested in me in any way. It may as well be an enchantment on my flesh.

But, I have taken a baby step forward. Like most people, “putting your money where your mouth is” can spur at least some motion. I’ve been mulling “investing” some small amounts of money into opportunities which have come up in regards to dating. One of them is going “premium” at OkCupid (one of the internet’s biggest free dating websites which I rarely visit and in which I got exactly one date with nearly a decade back) to look at the 25 women who clicked “like” on my profile (who for all I know may no longer be on the site). Another was signing up for an annual speed-dating event at this year’s annual New York Comic Con, which I have been attending ever since 2011. I’ve done speed-dating before, but this time promises a collection of women at least modestly (if not heavily) into the same geeky crap I am into. It’s an event which usually fills up weeks before the actual con, so time was of the essence. Yesterday, I plunked down my $20 digital dollars and signed up for the latter. So, almost six years after my last speed dating event, I have decided on that as my first foray into the realm of potential romance once again.

The con alone will be tiring, especially since I usually get little sleep beforehand preparing for it (atop of my usual work schedule). Speed-dating can itself be exhausting; it feels like dozens of job interviews at once. I could always flake out between now and the event itself and just decide to eat the twenty bucks and not bother. There is the chance that some “once in a lifetime” event or signing or panel could have happening at the same time and I have to choose. But, the very act of committing some (green) skin into the game at least makes it more probable that I will go through with it. So, at the very least, I will have another post coming next month.

Part of the dilemma is that as I am utterly inept at going with the flow or capitalizing on a crumb of a chance, I attempt to overcompensate by over analyzing things in advance. I call it “prep-time”, a term some fans throw about to explain how Batman can beat anyone given enough time to prepare. And part of that is trying to prepare myself, at least emotionally, for all of the worst case outcomes at once. And I realized that even if things go well with a woman, that doesn’t lead me towards any happiness; only another awkward moment and more potential for yet another deflating and frustrating outcome atop of all the others I have had in regards to dating. Say it goes well, I get a date. The date goes well, eventually I have to try to go in for a kiss. I’ve never kissed before, so naturally I’ll be terrible at it since I had no practice. A poor kisser is a mood killer for many women, and not for any unfair reason. But say that goes well and we have more dates; then I have to make further moves, or at least explain why I am not bothering while still projecting interest. Even the very notion of admitting my interest in a woman directly to her feels…off. I’ve literally never done that. I have literally never said or typed or communicated to one of the women I have ever liked, “I like you, I think you are beautiful/intelligent/etc. and would like to continue whatever”, not once. I always knew the outcome or feared it. I can’t imagine even taking off my shirt before a woman, what with the large lipoma on my back and a wart near my nipple, without imagining her even vomiting or sending me fleeing into the night with thrown objects. I simply cannot be that charming or handsome face wise towards a woman to compensate for this; and if I was, that would only cause me to become more suspicious. All this mental drama before I’ve even sat down and rotated or sent out an IM. You can see why I don’t want to bother anymore. It’s a mess for everyone.

At the same time, living in endless fear and underachievement doesn’t feel any more secure. The safety in endless misery only lasts so long. So, a baby step in one direction. We’ll see how it goes. I expect it to go poorly and be underwhelming. I doubt I am any more appealing to comic con women than I am to “average” midtown Manhattan women.

I do have one more past adventure to recount, which by now I have likely built up more than I can deliver with. I will get it typed eventually. I do think it is a doozy. But, all for another time, and another lonely night at the keyboard. Thanks for reading.

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