I love to check the search strings on my blog. A quite common thread is people that ask how can they help a socially anxious person. Of course there's the conventional path that they need to be encouraged to take and that I recommend: tell their doctor, find a therapist, read tons of books on the subject, read blogs and try to hook up with people that have the same issue, read blogs and try to hook up with people that don't have this issue, write a blog or keep a journal for their feelings, symptoms, etc.
In this post though, I'd like to talk about how to interact with them on a daily basis. The simple answer is just be there for them and let them know you are there for them. When I was pregnant I had a cyber-friend that emailed me each time I posted an update on the Preeclampsia Forum. Each and every time, I would get an email saying she's thinking about me, she's glad I'm doing well or sorry that I'm not doing so well. There were months when I didn't even get myself to answer those emails, but they kept coming. Thank you so much for those emails, N! They really helped.
So the long term solution is to reach out to them occasionally even if they don't answer back. But I think an even more interesting question is how to react to the emotional roller coaster they go through and they sometimes drag the other ones around into.
I stand by my previous posts ( see Dealing with Emotional People and Dealing with Emotional People - Part II) that when upset, you need to listen to their vent and empathise. Don't try to rationalize (it will just demonstrate to them they are irrational) and don't tell them it's all in their head. After they relax, make sure to reassure them that you still love them, you think they are fine, that this kind of meltdowns happen to everyone (an example of when this happened to you is great).
What about when they are overcome with shyness, obviously not being able to get over it: blushing, nervous, trying to say something, but can't, wringing hands, looking down, etc. I think you need to do the same: break the silence with a question, ask what are they thinking, say it's OK, they are fine, that you have time to listen. Don't go away trying to relieve them of their obvious discomfort, just help them go through it.
Sometimes the silence becomes so awkward for the socially anxious that they wouldn't start talking because the issue is too small and they made too big of a deal of it. This will extend the silence even more and make it even more awkward. All they want is to run away and hide. Don't let them run away. It will make them feel good for a short time, but will hate themselves later. Again, after the episode, make sure to let them know they are fine and you still love them. Don't laugh at how small their issues are.
The question that comes up in our heads time and time again after these episodes is: what is he/she going to think about me? He/she will run away and never want to see me again.