[openeyes]

I would tackle this by learning to embrace failure. Even if you went out with someone and they found you boring, what's the worst that could happen? You gain experience and are better prepared for the next time, becoming more relaxed each time as you find things much easier than expected. This is one benefit I received from working a couple sales jobs, making dozens of cold calls daily. After a while you see failure not as the end, but as a step bringing you closer toward success.

As for becoming interesting (as if you weren't already), check out Dale Carnegie's How to Make Friends and Influence People. A good listener can often be much more interesting than someone who never stops talking.