PJ (my fiance) has wanted to try out roleplaying for a few months, now. She's never done so, despite having friends that have and a brother that is in to World of Warcraft. It started as a joke, but eventually became a serious thought. I tossed the idea of what to around in my head for quite some time.
She's read Shelly Nazzanoble's Confessions of a Part-Time Sorceress, which uses Dungeons & Dragons as reference points. Due to that, I thought the best bet for PJ's first gaming experience should be a d20-based, fantasy game. I don't own any of the current incarnations of D&D. I own several 1st ed. products, as well as some of the retro clones in .pdf format. Alas, I did not own any core books. I've heard nothing but bad about 4e and remember very little awesomeness to WotC's 3.X product lines. So, I picked up Pathfinder. Several friends play it and enjoy it.
We worked through making her first character as a first level sorceress. It took a couple of hours and was painful at times. From there we moved through making up the rest of the party that will be accompanying her. We did a couple per night and spread it out over a week's time. We created characters of various races, arcane magic users, divine magic users, a rogue, and a fighter. She is by no means a master at character creation, but she gets it.
PJ wanted to get to know roleplaying before playing in a group setting. This would help her learn as many of the rules as possible and make her more comfortable come time for the big show on Sunday. I'll be running an one-shot for her and some friends.
I decided that for her 1:1 sessions, I would have her make up a gestalt style character. she went with a cleric/rogue. This would allow her to function in city situations, cast magic, and have some fighting abilities.
I also decided that I would use one of my own settings, instead of using a produced setting. My thinking is that I can tailor everything I need to fit where I need it to fit. I don't have to worry about what really belongs where and who is actually this person or that person.*
I have noticed that I tend to gloss over details that we history & arts type nerds know by rote. These very details can be very important to setting the scene. I know how far apart towns and villages would be and why. I know why different arms and armors would exist, what would lead to their development, and which cultures might even eschew them. All of my players do not.
You cannot assume that the player will know any of the conventions of the setting (or any setting). We all know that when you stay in the inn at the edge of the big, scary forest, you have to eat dinner in the common room. After all, you don't hear the good rumors or get in a fight by staying in your room eating your trail rations.
New players don't know to ask to roll to see if they know any local history. Therefore, they don't know that the big, scary forest, is a big, scary forest until they arrive at the big, scary forest and you describe it as a "big, scary forest."
Let them control the story. Let them describe some of the set peices in scenes. It gets more buy-in from them and makes them feel involved. With a 1:1 game, it also shares the responsibilities (and talking) in the game.
The first session went okay, after I got the story moving. I think she had fun, after all, she wants to play more this week and is looking forward to the one-shot on Sunday.
My game mastering in a recent game was lacking. Part of it was due to my waning interest. Another may have been that I had forgotten that while the above notes are very important to a new player, they're still important to seasoned players, as well. There were other reasons, to be sure, but these two may have led to my personal downfall in the game.
*And I can put my goblins wherever I damn well please.