[ScottyP431]

Boolean,

It's a question of do you want to put in the time to acquire the skillset of being an outgoing/talkative person. Gaining comfort and conversational skills will probably only come with practice. Just try striking up a 1 minute conversation with everyone you come into contact with. Cashiers, waiters, girls in line at the bank whatever.Seriously, you can easily do like at minimum 10 of these a day. 2 weeks later you will have no fear of social interactions because you just put 140 of these under your belt.

It's pretty hip on here right now to bash "The Game" and such tactics for getting women, but most of that stuff are things that nerds read in psychology books about general interaction and then backwards engineered (i say this since most of the original research was done on women, there is a good carol gilligan quote in the game about this) to apply exclusively to picking up women. I would specifically recomend you download like the Juggler post archives (its free). He talks about a lot of simple non trick/gimmick based ways to build conversational skills. Here is a quick outline of some that can help you:

-90/10 rule- when you begin a social interaction, most often the other person will be just as apprehensive as you are, so you need to supply most of the initial talking/conversation. Be willing to put in 90 percent. A real conversation is like a game of catch. You throw the ball back and forth. But you can't often jump right into normal conversation, you have to build to it. So be willing to do more of the work at first.
-Eye contact- this is huge, and a real problem i notice in many of my friends i would describe in the same way you (and others in this thread) have described yourselves. They tend to do this kind of weird shifty eye thing where they look at everything other than a new persons eyes. You don't have to stare down the other person, but make sure you employ active listening. Especially with women, if you just throw in some head nods and verbal agreements your results will dramatically improve.
-Dont ask a lot of questions at first. When you meet someone new, you aren't interrogating them. Everyone says the same [censored] "where do you live/go to school/work" etc and no one really cares to be asked or to hear the answers. Instead make statements about things that are interesting that would be a springboard for them to talk back to you.
-Emotional relevance- you want to talk about things that the girl (your GF's friends) can contribute to. You can't be like "oh god, last night i was 8 tabling 30-60 hi low stud when...." That gives them nothing to throw back at you. This doesnt mean you have to talk about Allie Mcbeal or oprah's book club though. Talk about travel, food, movies etc. Example

Girl: So where do you work?<lame question>
Boolean: Well right now i do XYZ<answer lame question>, but, I am probably gonna quit to go to spain and become a bullfighter. I really want to travel and pull a kind of hemingway drunken genius thing off for a few years.
Girl: I love to travel, i went to ABC and it was awesome
Boolean: Yea, i'd love to visit ABC, is it anything like DEF? I went there and this amsuing anecdote happend <insert anecdote>

If nothign else you can always fall back on talking about your GF because that is common ground you share. Make fun of her playfully
Boolean: So when you have a girls night out with my GF, does she make you carry all kinds of crap for her? Tongiht she tried to make me pocket enough makeup to do rupaul up for a week
Girl: Oh my god i know, she takes so long to get ready
Boolean: No crap, earlier today when she started to get ready, tehre was a stegosaurus outside our apt, thats how god damn long ago it was

Ok, enough meta level theoretical drivel. I know how you feel about meeting your GF's friends. My GF has a seemingly unending string of drunken hoes that shes friends with so anytime I am around here I have to meet 40 new people and it can be really annoying. Esp since girls make a big deal about meeting their friends BF's and what not. If I could break it down for you I guess I would say that a good short convo with meeting someone like this in a bar is like, actually, here is like a sample convo and then it can be broken down later, lets say you are at a bar and your GF Jen introduces you to her friend KT

Jen: hey, this is my BF boolean
KT: oh my god, I've heard so much about you (girls always say this for some reason, especially when they've heard nothing)
Boolean: Hi <eye contact> , nice to finally meet you, Jen has told me lots of stories about you and yalls debauchery together (most girls are now hooked, thinking "oh crap, what has jen told him)
KT: Oh no, i swear it isn't true, blah blah blah do you go to school with jen?<lame question>
Boolean: Yea i do, but i am considering dropping out to become a professional thumb wrestler/stamp picture photographer/astronaut, (whatever. Something fun and playfull that shows your sense of humor. )

As for starting conversations with strangers, use the 90-10 rule and just overload them with stuff. Dont worry about having the perfect opening line. Just say anything stupid. Today i was at the ATM and the girl in front of me was making a deposit and she reached for the left stack of envelopes and i said "no! not that one" and she kind of laughed and gave me the what look and i said "I had my eye on that one, take one from the back" , she giggled and took one from the back and we chatted a little. Just any kind of stupid thing can open as long as you are personable/playful and fun. A good one in bars is to critique the persons drink. Like if you are at a bar and a girl next to you orders a drink, comment on it.