Read This If This Site Makes You Feel Discouraged
Some people have told me that reading this site has actually made them feel worse than they did before. Basically, they were already struggling with an issue such as social anxiety and the idea that their people skills were part of the problem/solution wasn't even on the radar. Reading this site provided the double-whammy morale boost of telling them, a) your problem is bigger in scope than you thought it was, and b) it may take more work and time than you thought to improve. That's like being told at the last minute that you actually need to take another year of classes to graduate. Knocks the chair out from under you, or whatever that expression is.
Here are some points that I hope will make you feel better:
Figure out if you really could benefit from learning this stuff
Improving my all-around interpersonal skills helped me a lot in becoming less of an unhappy loser. I can't speak for your exact situation though. Take a look at your issues and your history and decide if a social skills deficit is part of the problem. You may conclude that you're mostly okay in this area and your concerns lie elsewhere (e.g., having more confidence, getting your anxiety under control).
This is a trite thing to say, but take things one step at a time
Lots of tasks seem overwhelming and intimidating when you have some distance and look at them as an abstract whole. Once you dive in and start handling the individual little tasks one after another it doesn't seem so bad. There's no reason you need to learn all this stuff right away or all at once. Pick an area that is important to you or which seems manageable and start with that. Once you've got a handle on that move on to something else.
Start with the easier stuff and work your way up
The articles I've written for this site can roughly be thrown into these categories in terms of difficulty. Other sources of information can also fit into this framework:
Any kind of general self-improvement that you can work on by yourself and at your own pace. Improving as a person has an indirect, though very real, effect on your social success. It makes you a more well-rounded, fleshed out person and allows you to take part in more opportunities. It allows you to genuinely connect with more types of people. Examples: making over your look, getting out more and doing fun new things, taking up an activity you can enjoy with other people in the future, making lifestlye changes, and reading up on areas you can talk to people about.
Trust me, if you were to take three months off from all socializing and just work on improving yourself by reading about people, the world, and things they know about but that you don't, you'll have a noticeably easier time getting along with folks afterwards. It doesn't feel like you're directly addressing the problem but it works in a 'wax on, wax off' kind of way.Any advice on social skills and the accompanying attitudes that focus on what not to do. It's usually less stressful to try and cut down on a trait or habit you already have rather than trying to learn a new one. Examples: Toning down your weird sense of humor, cutting down on the solitary video game playing, not debating with people so much, trying to be less touchy when people joke around with you, stopping negative cognitions and self-talk.
Any advice on social skills and the accompanying attitudes that focus on things you should do, but that just involve changing your current thinking. There are already people in your life. Try changing your attitudes about the pre-existing situations you find yourself in with them. Examples: Being more accepting of other people's annoying quirks, being engaged in a social situation instead of living in your head, having more tolerance for social unpredictability.
Any advice on social skills/attitudes that asks you to do something new, but that doesn't involve putting yourself on the line for rejection. You actually have to start doing things with other people here. Inhibitions can come into play, though they're not as bad as they could be. Examples: Speaking up more in conversations, joining in group activities instead of hanging on the sidelines, learning to make eye contact with people, trying out a new way to make conversation.
Any advice on social skills that asks you to do something and does carry a risk of rejection. Inhibited feelings start to become more of a problem here. Examples: Starting conversations with strangers, inviting someone to hang out with you.
Any advice on the opposite sex. I think for most people this is the most nerve racking area. Personally I felt my strongest feelings of inhibition and anxiety when I had to do things like learning to initiate conversations with people I found attractive, asking someone out, calling a number I got at a party, or 'making a move'.
Certain things may be easier or harder for you based on your unique situation. Start with whatever is the easiest for you. It will provide you with a foundation of skills and knowledge that will make subsequent steps go more smoothly.
Focus on becoming good enough to get by, not on being socially perfect
Don't feel you need to become the most suave, charismatic person in the world to be socially successful. Most people have some rough spots in their interpersonal skills and personalities, but they're good enough on the whole to get by. Everyone makes mistakes or comes off looking stupid here and there as well. That's no big deal as long as you're doing more good things than bad. Take dating as an example: You could be a little nervous, say some a dumb thing or two, and bumble the first kiss, but she could still like you because the overall package you presented was attractive. Have realistic expectations for yourself and you'll go a lot further.