[gs7]

By labeling his book outdated I actually meant the examples and situations he describes. The lessons learned and advice he gives are definitely timeless.

After reading everyone's suggestions here I realized that I'm not as socially inept as I thought. I do have the fundamentals down. I guess it's the lack of practice and not knowing how to keep a conversation going when you're not naturally interested in the other person that I'm having a difficult time with.

But I appreciate your suggestion on how to approach people at the Hackers & Founders meeting. I think this is what I need, tips on how to initiate a conversation while sounding natural. And LOTS of practice. Thanks!