I'm going to add on to jumpluff's post with two simple pieces of advice. Now I dont mean this in a "my advice is better than all the above" way, but I do really believe, at least for questions such as yours Pwnemon, that this is the answer that needs to be given but is often not.
Towards the end of her post, Jumpluff touched a bit on the first, but here are the two pieces of advice.
1) Put yourself out there
2) Learn to take and in fact embrace rejection
You don't have to look deep on this website to see the many posts of people that say, "i'm so shy and or socially awkward". Just look at the "could you be your own friend" thread for example. And as jumpluff said, people get turned on and reply to different things, therefore its almost impossible to give a one all answer to such questions. A Gary Busey that puts himself out there will MUCH more easily find a significant other and enjoy the company of many more women or men than a Brad Pitt that sits at home/minds his own activities/admires from afar. I guess you just have to ask yourself what is currently more desired by you and if you are then willing to make priorities and put in the time to learn the necessary skills to achieve it. Also that whole speech (read: excuse) one gives him or herself about their social barriers is VERY crippling. Maybe start with a simply goal of "i'll say hi to 3 girls this month". There is no end goal, no real purpose. You are just aiming to say hi to 3 girls, nothing more and nothing less (and as far as what you'll say after that, well just be honest. The beauty about being honest is that you do not need to mastermind a bunch of replies to have just in case for after that initial hello. When one is being honest, they speak from the heart and it just flows. How about this for a reply; "Actually, i'm very shy and socially awkward you see, and I am currently working on breaking that. I have set goals for myself and for one month my current goal is to blah blah blah"). And should you get rejected? There are hundreds of lessons to be learned in rejection so consider class in session ;). Now for a worst case scenario: lets say you just couldn't get the words or all the words out, then so be it. Just walk away and move on. I'm not saying this will be easy, but it will be a learning experience each time you try i'm sure. And obviously you do not want to do this at a place where you'll be seeing those exact people often. Rejection is a class in session, but its a painful one, and maybe try this at a mall or a park instead. Again, there is no end goal or real purpose. You aren't trying to ask someone out or get in their pants. This is just an example I came up with on the spot anyways.
Another example i'll use is that of the popular character Barney Stinson from the popular show "How I met your mother". Now i'm not saying that anyone should go about putting themselves out there the way he does (he is very aggressive in his ways but makes up for it in his sharp focus, amazing charm when he wants to, and just goddamn so smooth), but Barney is the perfect example of this concept. He is constantly, constantly always putting himself out there (to the point of severe overkill). Whenever he gets rejected, however, what's his response and mentality? "Whatever. I'm awesome". Essentially he just forgets about it and moves on without letting it affect him too much. And as for his powerhouse of a confidence meter he has? Well one can easily argue that all that cornerstone advice that is given, such as "more confidence", can and is learnt in between those two pieces of advice. There have been more than enough episodes showing Barney's beginnings, and not only was he absolutely terrible at putting himself out there, taking rejection, and even talking to women, but his confidence levels were abysmal. Another thing to note is when Marshall broke down Barney's success to failure rate with women on a chart, using math (one of my favorite episodes for oh so many reasons outside Barney himself), and for the ladies man and absolute pro that Barney is, he fails an insane amount more than he succeeds (which is just the perfect reflection of REALITY, and just as important, and that concept of putting yourself out there as well as learning how to take rejection). Barney, although perhaps an extreme example, still makes a fantastic one.
So yes, definitely take all the advice given so far that can be summed up simply as "work on yourself". Definitely do not ignore such great advice, but also realize that at the end of the day, putting yourself out there (and subsequently learning the ways of rejection and all the lessons it brings) is the defining factor.
A good luck wish to you pwnemon (and anyone else in a similar situation). With much love - your resident smoggirl, Mariah Carey.
Edit: nothing in this post was meant as an attack to those with social anxiety, awkwardness, etc, etc. Again, if one really wanted something, help can be found. Where there is a will there will surely be a way.