For the last five years, I've gone to Gencon and I've taken three girlfriends throughout. All of them had a good time. I think I began dating my girlfriend now (whom went last year) with hopes of finding osmeone else to go to Gencon with. I
HEre is what I do.
1. I explained before things got serious how fun Gencon was and how it's something that goes beyond dungeons and dragons. Women I find at first havea fewat that this is some kind of guy nerd mecha (and its not... else there would be no duct tape girl). They rarely realize how many things there are to do. Last year, I went with a former friend whom wanted his gf to go but she had turned them down. I told him to break out the book and go over some games with her and the girl nearly flipped when she found out they had a Euchra tournament. (go figure) . The girl I"m dating now had never painted anything before last Gencon, but everytime i did anything gaming i took her with me and she was facinated by "minis". That became a major driving force for her to want to go. (I have since heard Jen Haley's name 10000 million times) . She also found the "anime room" which I didnt know existed in the last 4 years. She had so much fun she asked me to go to Gencon Socal 4 months later (it was no Gencon Indy and not worth flying halfway across the country). Funny thing is she had only played traditional games until I showed her Guiltoine on our first date.
2. I make sure we play a lot of games together well before Gencon registration begins. I couldn't imagine dating anyone and not having my gaming in common with them among other things. Even if she isn't into dnd (whic my last gf wasn't) her and ip layed plenty of guilitine and monopoly. I have 40 games and there has to be something that her and I both enjoy even if its not dnd.
3. From the minute Gencon tickets sales gets postponed the first time in FEbruary, I start making this an "us" trip. We do all the planning together, we do our schedules together and we make sure to have games designated as "us games". Last year, after going through the trouble of getting his girlfriend to go, my friend completely abandoned his girl for his brother. I felt so bad for her (considering she also had to sleep on the floor while they shared a bed). This is th wrong way to get your girlfriend to go back. If you want her to go and make it something for yearsto come make sure you two have things to do together. Plan time to walk with her in the Exhibits hall. PRoudly hold her hands and tease the other geeks whom went alone. Seriously, set up dates where you guys, plan out schedules, talk about new games and always each year do something different you've never done together. In So-Cal i actually painted a mini, four months earlier I played some sci-fi rpgs.
4. FInd something else to do in the city. There's nothing wrong with taking a few hours of the trip and going to the museums, nice restaurants and even a movie while you're in town. All this does is broden the trip. Don't just send her there with lunchmoney. Sacrafice some hours and spend it with her there. Remember this is not a trip to gencon, this is a VACATION for the TWO of you.
5. See if there are local conventions in your area between now and then and take her. Build up to it. Playing dnd in a campgin and at a convention is two different things and you want to exose her to the rules judge and idiots well before hand. Plus small conventions give you guys the chance to find more games you have in hobby.
I hope this helps. IF its any help my girlfriend is sitting here with me helping me write this as we plan out our attack for event registration Monday.