[kjackson]

Sorry to be so blunt, but for someone who doesn't have any social skills, it's odd you would feel that Dale Carnegie's book is outdated. It doesn't seem like you are qualified to know what is outdated or not, given your lack of expertise.

I suggest you follow that book because it concentrates on the fundamentals. It's very important you internalize this.

When you go to the Hackers and Founders meetup, every 1 hr, walk up to someone and say "Hi, my name is gs7. So what brings you here?" It is awkward and embarrassing, but work through it. You'll get over it. At least it's friendly and people won't think you're a jerk. And then you can engage people on things that are interesting to both of you.

If you do this exactly 100 times over the course of several months, you'll find that it's not a problem anymore. All it takes is practice. You will fail miserably the first 40 times. The next 30 times, you'll do crappy, but you'll be doing better. The next 20 times, you'll be doing okay. And the last 10 times, you'll be good at it.

[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By labeling his book outdated I actually meant the examples and situations he describes.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!