Online dating is frustrating
There's a lot to hate about online dating in its current instantiations. Here are some specific things:
Having to find pictures of yourself, then posting those pictures publicly for explicit evaluation.
The near-requirement that said pictures depict you as someone who does interesting things in flattering poses (but not too flattering, which would be considered conceited, gauche, or both).
The commodification of romance: mobile-first apps like Tinder wrap up potential mates into swipeable little packages, whereas desktop-first apps like OKCupid assign to each candidate a numeric compatibility score. (Let's set aside the obvious hubris of an endeavor such as attempting to build a quantified scoring system for romantic compatibility that generalizes across place & cultural context, and instead dwell on the potential psycho-social effects of assigning numeric scores to all the members of an entire region of one's social graph.)
The persistent desire to continually check whether you have a new match and/or new message. This desire appears to operate at reptilian-brain level, where it is difficult to counter with well-reasoned temperance, and is particularly nefarious when paired with a mobile device, on which such checks can occur during almost any part of your day.
The incredible asymmetry of the straight-man and straight-woman experience. Men blast volley after volley of messages into the void, whereas women endure a constant bombardment of duplicity, misogynistic insults, and bad pick-up lines. This isn't good for anybody. For evidence, I direct you to this amusing casual experiment (a). See also this Cracked article (a).
The absolute arbitrariness of outcomes: as a straight man, you can do everything "right" (interesting opener; thoughtful, timely replies if the conversation takes) and still have the conversation peter out; whereas a throwaway opener and a half-assed conversation can result in a first date. And it seems straight women don't have tools for sussing out genuinely good fits from clever, duplicitous fellows who will just say whatever is most likely to keep the conversation moving towards a conversion.
As a straight man who takes pride in his writing, sending dozens of well-crafted messages into the abyss is an exercise akin to chewing crushed glass.
Perhaps the worst part is that the online dating exercise is only the first stage in the dating process. The online dating services purport to function as replacement for face-to-face dating, but in my experience they function only as prelude. This is not a problem, per se (and arguably the dating services yield higher-quality in-person dates by way of their sorting algorithms), but the additional time cost is real and shouldn't be discounted when comparing to alternatives, e.g. intentional celibacy or staring into a beer at a bar.
There's a lot to hate about in-person dating, too, in its current instantiation. I'm not going to delve into that here, because (a) I am less peeved about in-person dating, and (b) it (in some form) seems a necessary part of the romantic arc.
Is online dating worth it, despite its flaws? I'm acutely unresolved on the question. Inspired by Optimal Cupid, I've been giving it a thorough go for a couple weeks now, and have been frustrated & dissatisfied so far. I do think that my current efforts are pushing the needle towards going on more dates (thus making a satisfying relationship more likely), but the magnitude of the effect is unclear. It seems very possible that I could save myself a fair measure of psychic distress by abandoning the whole online thing and instead spending three nights a week reading novels in East Bay bars, without much difference in p(satisfying relationship).
But I don't think I'm going to give up quite yet. There's still promise here, despite the frustrations. A lot of my psychic distress is internally generated, and a more disciplined approach could yield similar benefit with a fraction of the cost.
What does a more disciplined approach look like?
Send thoughtful messages to three promising people a day.
Don't expect that anyone will reply to these messages. Don't feel bad when no one replies to your messages; it's not you, they're just deluged & fatigued.
Send-it-and-forget-it: there's nothing to be gained by checking in on how messages you've sent are "doing." Once you message someone, they will either reply or not. Follow-on messages aren't going to change the probabilities here, only add to the poor woman's deluge.
Have conversations with promising people who reply.
Keep conversational focus on arranging a first date (really more of a pre-date, just a brief in-person meeting to see if you are in fact interested in each other). Don't be fanatical in this focus – it's okay to chat for a while, and applying pressure isn't going to help anything.
Check the apps as little as possible (ideally, only once per day, but more realistically 2-3 times per day). If done properly, the whole shebang should average less than 15 minutes a day.
Simple enough. As is often the case, the difficulty is not in the framework, but in the implementation.
[rereads: 3, edits: phrasing tweaks. "shatterproof" -> "crushed" on a later reading, removed the bulleted list cause it looked bad. Written in my best DFW impression, whilst listening to the National's Slow Show on repeat. Somewhat reluctant to post this publicly, but I'm doing it anyway.]