but toward what end
Whether by dint of good fortune or through sheer force of will you happen to go on first dates with 63 strangers you met off the internet, dating is gonna drop some truth bombs on you. Some will be subtle, and others’ll hit you over the head.
Perhaps, reader, you may be wondering, “Wow, 63? Isn’t that emotionally (and financially!) draining?” You’re telling me, friend.
Here are my valedictory remarks – after 21 months I’ve learned:
That highly compatible aesthetic tastes regarding just about anything (music, food, art) tell you approximately nothing about whether you will enjoy spending time with someone.
People who entirely, 100% share your politics can still be jerks.
That there are innumerable reasons why someone may not respond to your advances online and that only some of them have to do with you. Even when they have to do with you, you were given such a small sliver of that someone’s attention that you cannot at all take it as an indictment of who you are. You just can’t.
That once you start getting kind, engaging, complimentary messages from seemingly warmhearted, decent people you are not attracted to at all, you’ll get why the nearly universal way of turning someone down in online dating is silence: engaging with those messages on a platonic level sends the wrong signal (it is a dating site after all), whereas a response that is forthright and clear in establishing you’re not interested in meeting your would-be wooer is no more fun to receive than none at all.
That you will experience a lot of firsts (& seconds, & thirds): your introductory messages will be ignored, you will be turned down for second dates, someone you date will refuse to exclusively date only you when you ask her or him to. These milestones will all hurt. Given enough time and dates they cease to be milestones and they become routine. Their being routine will strip these setbacks of their power to hurt you. The setbacks occurred – you’re still here.
That once you become inured to rejection through repetition (as opposed to intentional spiritual effort), when you no longer have any fear that you will not be desired, others will sense your equanimity and will be powerfully drawn to it. You will attract more romantic attention than you could ever realistically entertain.
There is a danger here: even when you attain a zen-like detachment from romantic loss, others are still breakable.
That the process of finding this out can rend your heart more than rejection used to, back before you were inured to it.
That equanimity being double-sided isn’t a mere matter of literal definition; that the same emotional distance that allows you to brush rejection off your shoulder with ease is in all likelihood an impassable boundary precluding true human connection.
That your friends will give you a lot of shit about how it’s wrong and deceptive to date several people at once, even if none of those several people have said anything to indicate they would object if they knew. He or she of your friends who is without romantic sin should cast the first stone. But still, they might be right.
After you date one person for a while, it will become impossible to remember how they appeared to you on the first date.
You kinda gotta wonder: how much of this increased dating success came from rigorous psychic self-improvement vs. how much can just be attributed to flossing with way more discipline and regularity than before?
That your ex, the one you lost and who you joined online dating sites to get over/transcend/replace, is not on those sites. He or she may literally be on there (and you are highly advised not to spend much time looking at or for the ex’s profile), but what I mean is a like-for-like replacement human being who looks like your ex, thinks and acts like your ex, and loves you like you fervently wished your ex still did is not. This realization is hard won. This truth is simultaneously both devastatingly sad and ok, somehow.
While adhering to the expectation that a partner should stand up and articulate what it is they desire (emotionally, sexually) can under some circumstances be a way to empower her or him and affirm his or her agency, under other circumstances that expectation can function as a self-serving rationalization for disregarding real power imbalances. That your partner may be, rightfully or wrongfully, too scared to ask for what they really want.
It is much, much easier to be the one to ask your partner “tell me what it is that you want” than it is to tell them what you want. That you shouldn’t pat yourself on the back too much for inviting someone to reveal themselves and make themselves vulnerable before you. That you should be honored if they do.
That if there’s anyone out there who isn’t kinda self-conscious and anxious the first time they sleep with a new person, I sure haven’t slept with them yet.
If you want to sound the depths of someone’s emotional seas, so to speak, you could do worse than to pay attention to his or her reactions to the gaffes or blunders that inevitably occur during sex.
That there are brilliant and thoughtful people who never went to prestigious colleges. There are vibrant, vital, creative individuals working shit jobs. The opposite of these two statements can also be true.
That contrary to popular belief, you should be most wary of dating those who are undamaged, or who have never really been sad.
A big reason people resort to hoary, unilluminating clichés (e.g., “I don’t feel a spark,” etc.) when choosing to end a relationship is because it’s goddamn hard to look someone in the eye and honestly tell them what they don’t have that you want, and to risk having it thrown back in your face, or worse: seeing someone you do care about dearly crumple in tears at the revelations.
That holding tight to generosity as a meta-level value to govern your interaction with lovers (and everybody else) – giving others the benefit of the doubt, recognizing that everyone else’s path to this exact moment has been idiosyncratic and has taken twists and turns you will never be able to comprehend the full extent of – isn’t just bleeding-heart altruistic/kind, but absolutely guides you to better choose which people are worth investing time in.
That someone who is rejecting you might be vulnerable and in need of your compassion.
That you are a complete and whole person even if any given individual doesn’t love you.
That that in you which one person sees as a flaw, the next may very well find endearing. This isn’t sappy sentimentalism – it is true; it is my lived experience.
That in online dating there are always new people to meet.
That this once seemed a consolation.
Or even: cause for celebration.

I got exceedingly bored at work and decided to drop by your blog. I really enjoyed this post. As someone who’s also had varied experiences with online dating, it’s interesting to see your perspective and where your journey has taken you. I admire your openness and optimistic empathy while meeting new people. You also avoid all those stupid pitfalls that most blog/magazine articles fall into when covering online dating (ie. your post is actually thoughtful, insightful, fresh, not another dreaded list with vague talking points).
So where does this leave you? Retiring, so to speak, from the online dating world? Or diving back in?
I appreciate your very kind feedback.
When I began this blog I was in the flush of what I thought was more or less total success with online dating; my enthusiasm was unalloyed. My basic stance was along the lines of “wow, does this ever work.”
My perspective on what it means for online dating to be “working” has shifted. It’s still possible to feel alone even while consistently meeting new intelligent, beautiful people – perpetually. I’m now past the point of thinking that the reasons why that could possibly be are contingent or entirely external to me. I want to know what it is within myself that could be a barrier to my experiencing love and joy.
I’m inclined to wrap up the project of this blog because while I feel reasonably qualified to advise people on the nuts and bolts mechanics of persuading strangers from the internet to meet them, I don’t think I’ve got a lot of guidance to offer regarding deeper issues that matter much more – establishing meaningful connections, tending to them, knowing when and to who to give yourself away, how to pursue what you desire without unnecessarily/unreasonably hurting others. They’re vexing.
Not sure the path forward from here. I now recognize that online dating isn’t a panacea. Where that leaves me (and you! dear readers) I dunno.
So glad I stumbled on this blog and this terrific, thoughtful post. I really enjoy your prose.
These lines really resonated with me: “That someone who is rejecting you might be vulnerable and in need of your compassion. That you are a complete and whole person even if any given individual doesn’t love you.”
Sending good vibes your way.
Right on! I’m heartened to hear something I wrote touched you. It’s been a couple years since I made these posts and I’m maybe a little less certain these days that I have meaningful wisdom to share with the world about love and dating. But if what I’ve shared here is useful at all, that makes me feel good.