ygolo,
You've got a laundry-list of things you want to change. If your discipline isn't strong yet, then there's no point in trying to address all of them at once. You need to commit to something and dedicate yourself. I would choose the thing or things that are easiest to change and have the biggest payoff. I think that going to the gym and working on being silly are excellent starts.
In terms of going to the gym, you just need to get out and go. There IS no trick, but it does get easier after you gain some momentum. It's hard at first and you need to force yourself. That's it. How frequently, per week, could you go (and actually maintain)? I thought 3 times was a fair amount, enough to get the ball rolling, but not overkill. 2 plus some other sports activity, - jogging, biking, yoga - would be okay too. Could you commit to that?
As for the rest,
But in general conversation, I tried to empathise with people too, but seem to be horrible at it. I end up asking things like "that must have been fun, huh?," or "how did that feel?" and I end up getting responses like, "What's with the 3rd degree?" after a while.
Sometimes you just have nothing to say, and that's okay. This isn't Late Night with your host, Ygolo O'Brien. You're a regular guy, probably more reflective that most. So, the first thing to do is to cut yourself some slack. You're going to make mistakes just like the people who ask why you're giving them the 3rd degree (pretty obnoxious, imo). Practice being silly. Instead of "conversing," just play for your own amusement. If people look like they want to open up, listen to them as best you can. If they look at you weird, that's fine. Maybe
they're not ready to empathize with people, just as you have your own challenges. If there's anything you can understand, it's difficulty socializing, right?
That has been on-going for sometime. Nothing particuarly conclusive, yet. I know there is a narrow set of activities I still like to do. I want to find more. But I am thinking, part of it is low self-esteem stemming from feeling generally incompetent at life.
Again, patience is important. How old are you? How many people your age would you consider competent in life? Otherwise, you can start making some changes to make you more competent. Working out is a great centerpiece that I'm asking you to dedicate to.
What does "flowingly" mean?
With grace.
I don't know about speedbagging my nut-sack (I think that'll hurt). But being silly is cetainly something I can try.
Okay, but make sure you nut sack is involved. LOL
Seriously. I process slowly. If people talk too fast, I get lost. If too many things are going on at the same time, I get lost. I am not a good driver, but I manage by avoiding the rush-times. I really suck at shooting games. I am most people's top kill when I play. In college, I got good at quake levels, by knowing where to "camp" to get a lot of frags (apparently this is frowned on). I'll check out Set and photohunt.
I process slowly too. Whatever. In some areas I'm faster than others, in some areas I'm slower. Set is still good.
How do I recognize a particular emotion in myself?
How do I recognize a particular emotion in someone else?
Yoga, exercise, and the stuff I wrote to Aelan to help get you in touch with your body and to calm down your mind.
How do I determine (in)appropriate/(un)acceptable behavior when the appropriate behavior is not spelled out? Assuming, in addition, that the behavior being judged clearly does not harm (or neglect to help) someone.
Looking for cues in your environment, and acting with confidence. Wit and playfulness is also a good way to disarm judgment and show that you're harmless. Your approach to socializing seems very intellectual, but doesn't have to be. The trick, I think, is to get in touch with yourself by giving yourself permission to fuck up and permission to not worry so much about fucking up, or about making a good impression and being accepted. If that means you turn quiet and contemplative, that's fine. Eventually, I think, you'll work into a "zone" where you'll know how to act and what to do.
Practice giving yourself permission to fuck up. Practice being silly at least once or twice a day and try and work it into social situations with friends. Hit the gym 2-3 times a week. Walk with focus and pride. Also, I would recommend watching a shitload of the Dog Whisperer on YouTube, although that's only icing on the cake. It's not a substitute.