Wow, has it really been 6 years since I posted this?
I'd like to thank EnWorld, and especially the posters in the thread, only a handful of whom do I still see posting on a frequent basis. The advice I got from this thread not only helped me avoid some serious pitfalls, but set me on a track to help and heal someone who has become very important to me.
First off, let me say that D&D is an amazing game, and it can do amazing things. In 6 years of gaming with her (the subject of the OP) and following this thread's advice, she has gone from the shy, anxious, quiet newbie to a confident, enthusiastic, take-charge gamer, and nominal captain of the group. And her transformation goes beyond gaming; she hosts dinner parties, and has become the beating heart of our social circle. Last month she was a bridesmaid in front of 100 people and she did great (even if she was having a silent panic attack!).
Two years ago, she took up DM'ing, and let me tell you; she is an
amazing DM. Her stories are engaging and creative, and she is fantastic at roleplaying, and she loves it. Now, I would say she still has a problem with wanting to please the players, but she disagrees!
I posted this to say that this situation has taught me that while we can't always bear the burdens of others, we
can always share them. Patience and understanding and can overcome just about anything, I think. I decided those six years ago after reading the advice in this thread that I was going do whatever it takes, and I spent a lot of my free hours counseling and listening, and most of all being sensitive to her needs and planning around them.
Anyway, I am super proud of this girl who has become one of the best friends I ever had and what she's accomplished in the face of her fears, and I am super confident that when we exchange marriage vows in a few short weeks, she will be brave in front of that crowd of people!
Thanks, D&D! And thank you, EnWorld!