I too am very socially awkward (cripplingly so) and have found it very tough to cope. I've started getting over my fears little by little because my problem I find is I'm intimidated easily so I would say for you to think about what the specific issue is for yourself that discourages speech. The next thing is to ask general questions to open up conversations. Questions create the most time in conversation and especially time sensitive or personal questions (relevant to your person or others) are what can create more continuous conversations. The other thing is to not really care about what the other person thinks and what I mean by that is always try to be aggressive. Obviously I don't mean be mean, but try to keep as active in a conversation as you can. Attentive listening, as I greatly know, is sometimes all some conversations need. And when the opportunity comes to speak your own piece don't be afraid of what you have to say or what others will think about it if you mean it with passion.
I'm a shy fellow around groups greater than two people, but I don't really mind. I have plenty else in my life I can enjoy.
one tip that I used on myself so I went from Fluttershy to Pinkie Pie irl: other people feel same way like you, so they are not in any advantage in social stuff over you, so relax and be yourself. Same thoughts you have, they might have too, they are also afraid to say something awkward, so they are in same position like you. with that in mind, relax and talk. maybe something you thought it would be awkward, they wanted to say as well, but were afraid.
I try to use the "Elfen Lied" approach, as incredibly dark as it is. The main character, "Lucy", does not view humans as other beings, but rather, things. Only those of her race (and a specific human) she views as people. It's definitely odd and difficult to do, but if you think about it, in the long run, minor encounters will be forgotten the next day.
Yes, I feel you :3 I've always been socially awkward. Well, maybe not always... I guess it started with being bullied at the lower school. It's basically that I'm constantly afraid people won't like me (anymore). It might sound silly to some, but it's always been and still is a huge thing for me. It can keep me from having conversations, even if I know someone quite well. Even here on this site, surrounded by the coolest people on earth, I feel that way from time to time. It still gives me the sads sometimes. But, it's slowly drawing in. The only thing I can think of is just to accept it and to sit it out. I know I've come a long way already, looking back on the scared little kid I once was. And I also try to live by these: - Do not blame yourself when you're going through an awkard moment. - Every now and then, if you feel you're able to, take that plunge and try to start a conversation with someone new. Even if it doesn't go well, the important thing is you tried. - Take it easy. You are fine the way you are, and not everyone has to like you. Not easy at all, but I'm trying. I suggest you do the same. ;P