Let's say you and I are talking:
* Me: I'm a lawyer [not true, just an example]
* You: Oh yeah? What kind of lawyer are you?
* Me: I practice international law.
* You: Wow, that sounds really interesting. How'd you get into that?
If you sincerely express interest in what I'm interested in, I will enjoy talking to you. Actually, even if you don't really care about a topic, if somebody else is passionate about it, the topic will be interesting. I learned about this from Dale Carnegie's How to Win Friends and Influence People, which is a great book you should read. I read this book in 7th grade and it changed my life.
If I were you, I would focus first on mastering social conversations with guys, before focusing on girls. I would also steer away from the PickUp Artist (PUA) community until comfortable talking to guys. At that point, you may want to check out The Game: Penetrating the Secret Society of Pickup Artists by Neil Strauss.
Also, it sounds like you have mild social phobias. I would solve this with exposure therapy (http://en.wikipedia.org/wiki/Exposure_therapy). In other words, if you go to some events and mingle, your stem-brain will get over its mild social phobia. A great place to start is meetings at your local Toastmasters.
In summary, rather than look for a quick hack, I would focus on achieving small victories, like attending Toastmasters meeting regularly, and getting better at conversation.
Good luck man!