When I outlined this essay, I planned to dedicate this section to caveats. Namely, I intended to pre-empt any reaction that I’m an unattractive, shitty personality’d brat who’s bitter because she never gets asked out, and who prefers to blame the rest of the world rather than recognize her own part in her destiny. [In fact, I am passably attractive and reasonably personality’d, and I get asked out far more than I think my own desirability justifies.]

But then I had drinks with a good guy friend and realized that I need to acknowledge a much more cutting and depressing possibility for why the social scene here is what is it.

You see, the guy friend with whom I was splitting a bottle of wine is a stud. He’s great looking, hilarious, athletic, and successful by all conceivable standards. He’s starting a company and pursuing artistic interests on the side – and he’s actively looking for a girlfriend.  And he gave me thirty-odd reasons why San Francisco sucks for men, too.

Our common complaint started with: “where are the good-looking, ambitious, accomplished and interesting people in this city?” But as we drank more wine, we got more honest: we’d both been on plenty of dates with very good-looking, ambitious, accomplished, interesting (not old) people. And, we both conceded, there wasn’t a single one whom, if we never saw them again, we’d remember to think about.

What kind of person says that?? That is, what kind of people are my guy friend and I to be so dismissive, and is it possible that San Francisco is not so bad because it has a lot of geeks and marrieds and gays and male cougars, but because it has so many of us.

And what are we? We’re the ones who excelled in our small town high schools, netting us a place at prestigious universities and, from there, elite jobs and enrollment in competitive graduate programs where we were further groomed to think we can and should do anything to which we set our minds. We’re the ones parents and teachers tapped as “high potential” when we were 12, at which point we were given permission to focus all our attention on ourselves. While the geeks were developing their computer programming skills, we were becoming experts on the art of self-perfecting. We collected accomplishments for broad-if-not-deep resumes and prepared ourselves for roles as future leaders of America.

Why do we come to San Francisco? It’s partly because we can’t go back home – our peers from New York and London are starting to migrate back that way, but the places we come from don’t afford the opportunities we’ve been bred to pursue. But it’s partly because, as it always has in America, the West Coast represents the next thing. And that, in the end, is what people like my studly guy friend and I are programmed to seek. It’s not goal-orientation, its progress-orientation. It’s the reason most of us have never stayed at a company more than two bonus cycles, the reason at my one year business school reunion the predictable answer to the question “how are things going?” was: “Fantastic! Totally kicking ass…..But I’m keeping my options open, you know. Have you heard of any interesting opportunities lately?”

How does this translate to personal relationships? A desperate fear of settling, an overly-attuned eye for flaws, and a thirty-year habit of uninhibited self-prioritization.

So it’s not that there aren’t a lot of check-all-the-boxes men and women in San Francisco, it’s that, when you take out the engineers, the marrieds, the gays, and the older men, that’s all that’s here. For all its transplants, San Francisco is a homogenous city, a pot of overachievers whose normal means of standing out fall flat. Try impressing someone at a bar here: Went to a prestigious university? Where else would you have gone? Starting a company? Aren’t we all?  Have travelled to 21 countries? Only 21? Recently ran a marathon? Why not an ultra?

But here’s the big thing: all those achievements apply to women and men. If you didn’t hear the voice, it would be impossible to tell whether a bio (“I studied History at Harvard, then worked at BCG, then went back to Harvard for business school. During that time, I biked across the United States, hiked Kilamanjaro, started a nonprofit in Africa, and now I’m head of corporate strategy for a start-up travel website”) is that of a guy or a girl. Which complicates gender roles beyond logistics (whose career do we prioritize?) to fundamental worth (what do you bring to this that I don’t already have? What can you provide that I couldn’t provide for myself?).

In short, I fully acknowledge that there’s another piece of this argument, which is that San Francisco is so bad because the women here are so difficult. Were I a man here, I would be complaining that I “just can’t win” with women in SF: that they’re expectations are simultaneously incredibly high and very poorly articulated.  I think the Hong Kong geek from my cocktail party had a point, if badly delivered: the women here have replaced traditional feminine charms (no one would argue that focus on personal appearance is significantly muted here relative to other cities) with gender equal pursuits. And yet we still expect to find a man whose power and ability-to-provide-something-we-can’t-provide-for-ourselves stirs our respect and desire. Men, meanwhile, understandably want to be with someone whose achievements and pursuits complement, not compete with, their own. Which makes you wonder whether gender equality is necessarily emasculating, and what that means for a generation bred in it.

And so maybe all this ranting isn’t so much about the city as about our generation, and what’s so bad about San Francisco is the sobering reality that it’s the frontier toward which we’ve been driving. It’s the city that’s creating tomorrow’s companies and setting the standard for social progress. It’s the mecca for people who want to change the world, from geeks to entrepreneurs to Self-Reliant Overeducated Thirty Somethings like me. And it leaves you wondering: where is all the progress taking us, when meaningful relationships seem so difficult to find and maintain. Is this really the world that we want? And is there anywhere else to go?