|Really old gamer|
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I started some years ago... Let me tell you, it was a different game back then. We didn't have numbers for hit points yet. I used to hate the cruddy bottle caps we used back then. Ah yes, bottle caps. Back in my day, there were real drinks. Soft, fizzy drinks, and we could all drink as much alcohol as we wanted because there were no laws about it yet. I had a girl once, who used to wear blue dresses. But public transportation... Wazzat? Speak up. Characters? Yeah, I played a level two fighting man. He used to whack people with a bohemian ear spoon... Zzzzzzz...
Ok Lune if you're going to GenCon I think you have to repeat have to take your son to True Dungeon! What better culmination of gaming than to actually embody a character? Also maybe after con start a world of darkness campaign, the themes in that tend to be very mature and the Storyteller system is a great counter balance to this rules heavy system. Last idea if he's not ready to run a game you could GM his idea for a game he would be a cowriter. I hope you find this helpful and maybe ill see you guys at con.
Kendrosthenes: Thank you for your suggestions. Scavenger hunter ... hmm, that gives me something to think on. I would like to take credit for being a selfless parent in raising my son but to be honest he has made it easy on us. He shares a lot of interests with both of us so it makes it easy to support him as we all enjoy the same things. :)
Scythia: Hm... that gives me an idea for the above Suggested Scavenger hunt.
Popupjoe: I was planning on checking that out. :)
Also I have been thinking of getting him to design some scenarios but I think he may need some help starting out. This could be a good way to help him transition. Thanx!
I just want to second any of the 'have him GM his own game' options.
A far as finding a group goes, I don't know where you live and what the gaming community is like but I'm sure you could find some people willing to help out, even if it is just the rest of your normal group.
A PFS scenario is a great idea for a start, but since you say your son is quite mature and intelligent I would suggest that you as a player not be afraid to go off the rails (but know the limitations to this, you should probably know the scenario as well or better than if you were planning to run it yourself).
Challenge him and let him know that the success of the night was his doing and not some Paizo author's.