An additional concern is not being able to find women with compatible intellectual interests (I don't mean having or not having specific interests but being interested and capable of thinking/talking about intellectual topics). Fortunately, there are dating sites. OkCupid seems to trend smart, but there are lots of others too. If you live near a good university, you can also attend evening special lectures and events of that sort that are heavily attended by graduate students. They often have a socializing aspect to them after the event.
I don't live near a university (the local Christian college does not, IMHO, count). I've tried dating sites, but never had any luck with them. I tried a meeting of my local professional society, but I was one of three people under 50.
Damn! That's exactly the kind of vague advice that HughRistik decries.
I wasn't trying to communicate a thoroughly systematic method for acquiring social skills, so I confess that this phrase may have been a bit vague.
That said, it's English, not a formal language. "Just get out of the house" does not mean, "position yourself in some location X such that X is not a member of the subset of locations within your house."
The expression means that one should get out of the house and go to places that are conducive to some form of social interaction. Appropriate places vary tremendously from person to person, which is why the phrase is so non-specific. But if you pick some social event or scene where there are likely to be people vaguely similar to you, and you keep going to these events, there's a pretty good chance you'll meet interesting people and get better at socializing generally, if you need work at that. Hell, as long as you pick some social event where you don't actually have contempt for everyone there, and you keep going out even after things go poorly, you're probably going to do OK.
You can't expect to be a great skier the first time you hit the slopes, and if you give up because you're falling too much, you'll never even be a competent skier. You can't expect to have decent social skills if you don't make a sincere effort to socialize. I understand that, in some cases, people sincerely try, deal with falling down a lot, keep trying, and still fail. I admit I have no easy solution for that. But I think that's a pretty small minority of cases. If I'm wrong about that, please correct me.
"But if you pick some social event or scene where there are likely to be people vaguely similar to you"
I suspect that for most of us, such scenes consist almost exclusively of dudes.
I have trouble meeting women, and it's due to three major constraints:
1) I'm not religious, so church is out.
2) Bars bore me.
3) I haven't identified any other venues where a 30-something guy can approach women in a sociable context.
These constraints may be typical of the Less Wrong readership.
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It's not at all clear to me why I'd enter the classroom in the first place, unless I had a corresponding roomful of women and was going to play Yentl for my own amusement. I don't really consider myself someone with expertise in the matter! Apart from a few vague hints like my remarks about meeting people through other people, I've confined myself to ethical claims, not practical advice. My ethical claims have been peppered with reassuring remarks that they don't spell practical disaster (excessively demanding ethical philosophies tend not to be very popular), but they are still just ethical claims. I don't have that stellar of a dating history to draw on for practical help: mostly, I collect admirers through the Internet and they turn out to live far away. In terms of actually going to a physical location alone with a romantic interest on an explicitly-purposed date, I've been on two.
There are really two problems here. The first is that single men and women can have a hard time meeting each other. The second is a mismatch between the expectations of each and the reality.
We all have an idea of what we're looking for in a mate. That idea owes a lot to the media, and it isn't all that realistic. She is looking for a man with smouldering good looks and a deep sensitive streak (full disclosure: I'm a man, and most of the time I don't even care about my own feelings). He is looking for a woman who is paying for her math degree by stripping. Only very rarely are these expectations fulfilled.