I am a recently single guy and just realized how hard it seems to be to meet new people (men or women) in the City. One craigslist post summed it up well, “Ever notice how people (downtown anyway) just walk right past each other, no eye contact? Creepy.”
I heard a great Perspective on KQED on a closely related topic: why do we crave proximity but not intimacy with those around us?
It seems like after college there is no regular, required ‘mixing’ environment. University offered 5-7 new classes each semester, a forced shared living environment, and communal extracurricular activities.
Of course, there’s always the workplace, but that’s often ineffective. Coworkers are in varying stages of life connected only by an employer, not a shared desire to meet others.
Bars are okay, but alcohol gets in the way of real interactions. In the City, Zeitgeist is a good bar for meeting people, especially when it’s busy and you’re forced to sit next to strangers.
KQED Perspective: Proximity Without Intimacy
kfarr 
I definitely agree with you about the lack of (set up for you) social mixing after college. I guess that’s the same in any big city, but I think Japan’s even worse because the culture generally says to stay to yourself. It’s almost imaginable for people here to talk to strangers just for smalltalk. Sure if you need to ask directions or something you can, but you almost never would expect some random person on a train or walking down the street to talk to you. It’s not that people are unfriendly – they’re just taught not to talk to strangers.
I’ve recently been hearing from a lot more Japanese people that internet sites like Facebook are being used to meet people. The community features on those sites are used to meet people with common interests, and oftentimes for meeting in real life. It could just be me, but I’d be a little hesitant in meeting people from the net. I guess over here they feel more comfortable having a website or group as their middleman.
I don’t know that I agree with Anthony about meeting people you met over the internet. I will say that I used eHarmony for a couple of months as a way to try to meet people since I was experiencing the same problems, and it was utterly disastrous. Even with a big city nearby (Chicago) to draw from, the kinds of people were not always top notch, and a lot of people seemed hesitant to get together to meet despite the fact that we were using an online dating site, which seems ludicrous since the entire premise of online dating is that you meet people online and then get to meet the interesting ones in real life. Despite my bad experience, I don’t think meeting people online is such a bad thing. It isn’t any riskier than meeting random people in a bar, and at least there aren’t as many awkward moments where you’re feeling someone’s personality and interests out.
Of course, the indecision and weirdness of meeting new people gives it part of its charm.
In talking with other friends, I think that the biggest difference that people our age need to adjust to when leaving school is that there aren’t any “required” meetings anymore, so we have to make a conscious effort to put ourselves in situations where we’re able to meet with like-minded people. Really, bars are huge social mixers where not everyone is going to be compatible. For myself, I never met people that I felt were worth more than a date or two at a bar or club. I would recommend more things that are events that would draw a specific crowd, whether it’s a concert by your favorite band, a houseparty from some of your friends (they need to bring their friends as well, that way you can poach from their extended social network and work associates as well… i’ll get to that in a little bit), church if you’re into that, political events, museums, exhibits, poetry readings, whatever. You know what you like, and people that like some of the same things as you are a lot more likely to be interested in talking to you than the girl with the knockoff purse and snooty lips sitting on the other end of the bar.
In no uncertain terms, should you ever try to date people you work with. Please, don’t shit where you eat. It’s bad etiquette and asking for a problem if things go south, or even if you hit a rough patch. Plus, a lot of workplaces have rules prohibiting office hookups, so you could get fired. Meet people that your friends work with. That way, if things go bad, they have to deal with it instead of you. Hahahahaha.
Anyway, that’s the end of my rant for today. Sorry to hear that you’re on the market again after so long, unless it’s a good thing, and then congratulations are in order. Take care.