Hmm...I don't have much advice on the pickup thing because I've never done that before, but I do have something else to say.
People have said this before, and I have discovered this on my own, that society does pressure you into getting a relationship and all of that juicy stuff. Movies, TV shows, songs on the radio, and seeing everyone you know get into relationships...a while back, I felt like **** for being single. On top of that, I would come to this site and reading a whole crapload of field reports, all of this about people getting head, getting laid, making out, and all of that. True, getting in a relationship is fun and it will make you happy. But there are some things more important than relationships. I would say don't do it if it's only because you feel left out.
Anyway, I don't know if I would randomly call a girl I don't know. If your friend knows her...maybe get him to hook you guys up somehow? Or do something with both of them and get acquainted.
As for conversation...I had and still have trouble with that too. You might try reading "Psycho-Cyberentics" by Maxwell Maltz. Conversation is easy, and it shouldn't be a form of work. You don't HAVE to make the other person laugh, and if you consciously try to, you won't pull it off. If you are worried about being boring, it won't work either. Just try to have fun. When you aren't trying to impress someone, when you aren't worried about what they think of you, or when you aren't consciously thinking about something witty to say, it is the easiest thing in the world. If you read Emerson's "Self-Reliance", you will also realize that other people are thinking the same things as you. Other people are equally worried about the impression they leave on you and are equally as insecure. When you realize that, it gets easier. After that...I started treating other people as I wanted to be treated, and it worked.
Sorry if I rambled a little bit, hope this helps.