Earlier quoted context omitted.
I think using your analytical mind to affect your attention and behavior in social situations isn't the best way to learn social skills, because it's too easy to come across as creepy if you don't have the right "feel" for doing these things. My own approach is more about unlocking another part of your mind, to which socializing makes sense natively. It's a bit more inwardly focused, but still supposed to be used in…
I think these techniques are initially analytical in nature, and may seem forced, but eventually it becomes habit, and you don't have to think about it on a moment-to-moment basis. Your last sentence is interesting, but quite a cliffhanger. Can you expand upon your technique or point us to some resources?
The overall approach was inspired by the book "Drawing on the right side of the brain" by Betty Edwards. It starts with some simple exercises that don't teach you to draw per se, but get you into a strange inner state where drawing makes sense. (Repeating real world curves and angles with your pencil without looking at the paper, redrawing a sketch upside down, etc.) It works incredibly well - an adult with zero artistic skill could do these exercises for a couple hours and get a strong sense of "holy shit, I can draw anything I want!" It really feels like you're unlocking a part of your brain that was always there. And the upgrade sticks with you for life.
The point is that I think many skills, especially those with a bimodal separation (you either get it or don't), are really about your inner state. The right inner state is hard to teach, but it can be taught, and then you gain the skill quickly and almost miraculously. For example, all those infuriating people telling you to "just be yourself" are referring to some kind of change in inner state, but haven't found the key to communicating it. For drawing, Betty Edwards has found the key. For social skills, no one has found the key yet. I'm skeptical that my approach will work for everyone, but I'm certain that self-experimenting on your inner state when around other people is more fruitful than trying to force things with them (bravely approach! pay attention! ask them about their job!) It might take a long time though. For me it took years, and only after I stumbled into the right state a few times by accident.
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Anyway, if you want to follow me, here's what I would suggest. All training must be done while you're around other people, and the first step is noticing just how much information you're sending out. Many nerdy folks don't even fully register their own mood - how good or bad they feel at any given moment - even when everyone around them can see it plain as day. To me it felt at first like a firehose of information, much of it negative, that I couldn't help but blast at whoever was close. (Not through words! Through my pose, my eyes, etc.)
One way to notice it is by contrast. Watch a clip by Sean Paul, and imagine that everyone around is constantly comparing you to him. That's the firehose. It's very hard to change, because it feels like "water", a part of what you are. And it's hard to accept that the true reason people don't flock to you is your low-grade depression. It feels unfair! But becoming hyper-aware of it is the first step you must take.
When I'm socializing, the focus of my mind is being aware of that firehose of information. It's easy enough to redirect when it feels nasty (just turn it away from other people). And if I deliberately ignore what I want from other people, and focus entirely on making my firehose a bit less off-putting to them, I can slowly affect change. Breathe out, breathe in slowly, don't lose touch with the immovable object, and very carefully make it move.