Finding the (Im)perfect Strategy

As 2015 comes to a close and I am every bit the Dateless-Man that I have ever been, I’ve been trying to take stock of where I stand and what my options are in the realm of dating. This began after the conclusion of the New York Comic Con speed-dating event that I chronicled two months ago. It’s since become more complicated over the past few weeks as I’ve seemed to make a new “friend” online as well as face “shadows from the past“. As the (probable) last blog post I make this year, I figure this is as good a chance as any to take stock and weigh options.

I am still caught in a crossroads between abandoning all hope of dating success on any level and embracing a life without any prospect of love or attraction and making one last great push before that big “4-0” hits me. I thought I had time during my 20’s but inevitably I didn’t, and things didn’t work out. After all, despite a movie, life as a 40 year old virgin isn’t any easier than life as a 30-something year old virgin in terms of dating; in fact I imagine it is harder. At least now I am still in (somewhat) of my physical prime, at the very least. And if there is one thing I may have genuinely improved upon over the past few years, it is being able to make small talk. I do it all the time for work to hundreds of strangers a day (albeit over the phone, with strict professional regulations), after all. I’ve faced plenty of hardships and tribulations since I graduated college. The challenge is not only convincing myself logically that it is worth it to invest time and money (which is very finite) towards pursuing this when statistically there is no reason to believe I will have any success.

Ideally, this means finding as perfect a strategy as possible. I need a venue or setting which caters to what few strengths I have. Unfortunately, this may not be as easy as it sounds. Short of telepathy or a change of either planet or dimension, I don’t think such a setting exists.

Having officially tried “speed dating” four times across six years, both with “mainstream” and “geeky” women in attendance, I think I can stick a fork in it and consider this option a failure. It’s a quick way to try to “catch up” and meet as many women as possible in a short a time as possible, but the format hasn’t favored me at all. My theory all comes down to competition. In some small ways, especially in a capitalist consumer place as New York, we are all competing with each other. Most of this is indirect, just living life. But some dating venues encourage direct competition with other men for the affections of the opposite sex, and “speed dating” is one of them. Those men who are the most appealing will get most of the attention; there’s no need for any of the women there to “settle” or have to risk being dismayed with a pick who offers less than she wants when there is literally another dude waiting in the wings in 3 minutes (who she may have already scoped out at the start). Even literally being interested in “every” woman at such an event doesn’t assure getting a shot. It also encourages a quick break when there’s no chemistry, or even when there’s some, just because of the format.

Unfortunately, what other options are there? School is over, and my social circle is small and made up of friends who are almost all “coupled up” and busy with their own lives or fellow men who are also single and thus more mercenary. Nobody ever “sets me up” and at this point I may not trust anyone who attempted to do so, as I am aware that my perennial datelessness is at best a subject of mockery with them at times. I don’t do well at bars, due to the loud music and the fact that even single women are often with friends and that makes talking to one harder. I don’t get invited to parties and, again, those encourage direct competition. I did get one date from OkCupid, so there is always online dating. However, with that I am at the mercy of a picture and a profile, when women are so deluged with options that many have to heavily filter their settings.

At best I would need a venue or setting which is as non-competitive with other men as possible while also allowing what few good qualities I have to be on display. Outside of relying on others to “set me up” or complete, random circumstance, I don’t know of any venues which can cater to me. As such, do I seek out to become more “zen” and abandon all attempts to date due to my own desires or a sense of having zero options, or both?

I have a lot of things to consider for 2016. As always, I will keep this blog in the loop, as it has helped me greatly to order my thoughts and vent my feelings. Thanks for all of those who read and comment. Have a great new year!



Dateless-Man vs. Shadows of the Past

At least this blog post title sounds dramatic, right?

It’s December again, which is usually the time of year for reflection, corporate mandated “cheer”, the commercial exploitation of Christmas, and eventually New Year’s Eve. This is usually the period of the year where my depression tends to hit a fever pitch (from October thru March), and I imagine I am not alone in that regard. The holidays can be rough on anyone for many reasons. This year hasn’t been so bad, thanks in some part to the fact that I do have this blog as a “safe space” to vent and order my thoughts about things outside of my own head, and have had it for over a year now. Considering my mother’s wavering health, I am one crisis away from the deep end, but for the moment I am probably better off than I was last year.

I continue to be stuck in the middle of a crossroads in terms of my romantic lot in life. The path of the mind which wants to intellectually abandon any thought of pursuing anything further, considering my litany of failure, frustration, and regret. The path of the heart is anxious about growing older (even further past 30) and yearns for companionship at times, believing that things are different now. I want to give up completely (as opposed to having given up about 99% of the way), yet such a thought hardly makes me joyful. Yet as fate would have it, I seem to get reminders of my pathetic past at unexpected intervals. I imagine it makes the blog a little more exciting for those following along, but it still feels odd to me.

Strangely, this links directly to an installment from last December, when I was still in the midst of “Dateless-Man: the College Years”. In involved a young woman who was a friend of a friend who I’d met in high school and continued to sporadically run into briefly during college (who I dubbed “Sybil“). My recent “friending” of her on Facebook inspired a brief look at my interactions with her. Naturally, they involved having a crush on her but being too hesitant to make a move beyond writing a “love note” to her which went undelivered. We haven’t interacted much online since, but out of the clear blue sky she messaged me last week. It was a completely innocent thing; the company that she works for is hiring and she was trying to sort out which of her old pals may be interested. By this time she’d long since had a boyfriend, as her Facebook home page made very clear. Sybil insisted on talking over the phone, so we did.

It wasn’t long before what began as a simple professional inquiry devolved into a bit of a gossip session with me filling her in about the old crew of mutual friends and whatnot. Despite some “hard right” political views vented online, Sybil remained just as sweet and easy to talk to as she’d always been. Before I knew it we’d talked almost a half hour, which is a rare thing for me to do over the phone. She spoke about her boyfriend a bit, noting that he was “kind of a nerd” and trying to see if I was interested in hanging out with them (and their other pals) to play some strategic “Star Trek” board game he had. I joked that she was “trying to arrange a play date for him” since she’s very tolerant of “geeky stuff”, she isn’t actually into it beyond casual exposure. The phone call ended well, just catching up between two old friends.

Yet it’s impossible to chat for a half hour with a woman who you used to have a crush on without some old memories and regrets from the past resurfacing. I haven’t carried a torch for her, I don’t for a moment think her contact was anything beyond reaching out to an old friend, and I have no intention of pursuing anything romantically with her. That ship sailed a long time ago. No, the regret came from the past. Hearing Sybil talk about her new boyfriend and her devotion to him despite his “geeky” hobbies to the point that she was trying to find people of similar interests for him to hang with made me wish I’d been bolder when we were younger. While I am still glad I never delivered the “love note” (as it was both embarrassing and depressing, as I essentially revealed my feelings and then apologized for it), it made me wonder how things would have turned out had I asked her out in person back in high school. Naturally at the time I didn’t because I doubted it was mutual and feared gossip; yet chatting with her now made me remember that Sybil always came off as too sweet to want to do anything like humiliate someone who asked her out (at least so long as I wasn’t a jerk about it). If things had worked out, however briefly, Sybil might have been an ideal “first girlfriend” for me. She certainly wouldn’t have rushed me outside of my comfort zones, and even if nothing got physical (as the rumor around the schoolyard was that she was “waiting until marriage” before having sex, though lord knows if that was true then or now), it probably would have been pleasant.

When most people think about their past experiences with love and the opposite sex, there is usually a mixture of things ranging from success to failure to embarrassment to passion and so on. Most of all I have is regret and one sided frustration. I should have been bolder as a teenager, but it felt impossible to me; I never thought such a thing as a woman liking me back was possible. Speaking with Sybil now was fun, but it also made me realize that I should have taken a chance when I was younger. I had very few opportunities for love as a youth, and one way or another I botched all of them due to what I can only summarize as fear. I covered some of this before in “Reflections“; consider this an addition to that.

I’ve gone over my own pathetic past with women over and over and over again. I’ve looked at things in different ways ever since starting this blog, and that’s good. While it sometimes took me a decade to see things differently, I have in some regards. The problem is reliving a past which was unsuccessful and frustrating in terms of romance in every regard. I can look at it from a new angle or revisit it but in the end it is still the same. It’s the past I am stuck with, which in the end always leads to one future; me being the Dateless-Man. There’s nothing in it which I can use as emotional ore to force ahead, but there are still some pleasantness within it, such as making friends like Sybil. It links me to others and my own strengths but it also keeps me trapped in my own failings. There’s no way to get a second chance or a do-over, and no way to resolve those regrets.

Happy holidays in case I don’t type again before 2016. All I want for Christmas is to be somebody else.