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Where to start? (Pathfinder or 5th Edition D&D?)

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My initial advice would indeed be to check if there's an existing group somewhere he can join. If there is, best for him to start with the game that they play.

If there's no group he can join, or things are otherwise equal, I would say start with the 5e Starter Set. It's a good one. (The Pathfinder Beginner Box is also very good, but the jump from that to the 'real' game is much larger than with D&D.)

And with 5e there is no need to jump yo the full game after level 5.

The 5e basic game is my suggestion. That's what I am using with my kids (6, 9, and 14). Though with the release of PDFs of the 4e essentials stuff I am tempted to run that with them, but will probably stick with 5e for a while.
 

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I've run Pathfinder Beginner Box with 7 year olds, worked very well. No way would I recommend full Pathfinder, though. 5e seems a lot more practical, but my 8 year old greatly prefers Mentzer Classic D&D to any other edition, as long as he starts at 4th-5th level with a dragon. :D
 

I'm also going to put in a vote for 5e, and I recommend using the starter set. It's fairly cheap (especially through Amazon), and The Lost Mine of Phandelver is a pretty substantial adventure. (My group got about 40 hours of play from it.)

Another alternative would be Swords & Wizardry WhiteBox. It's derived from the original White Box/LBB version of D&D, and the rules are incredibly simple. It makes for a really fast and freewheeling game that I think would be perfect for an 8-year-old. Better yet, the rule book is a free download!

http://www.swordsandwizardry.com/?page_id=6
 

If he wants to PLAY D&D, then any rules set is fine - the GM will be handling most of the heavy lifting with regards to rules and all the kid has to do is roll dice and do some basic math which will be spelled out right there on the pre-done character sheet the GM will make for him, after going over some basic class and race question-and-answer with him.

If he wants to RUN D&D, then things get a little more complex. If he and a group of friends want to try the roleplaying experience all on their own, then they might be better off with the Basic Box D&D (if you can find a copy of it -- failing that, try to get a copy of Labyrinth Lord). You might want to consider DO: Pilgrims of The Flying Temple. You might want to have them try Old School Hack, which has simple and clear instructions, along with strongly-typed classes.

There's also No Thank You, Evil.
 


The Pathfinder Beginners Box or the 5E Starter Set are probably both fine. Though the 5E basic rules I think are a better longer term option.

If you go old school...as the DM, you will have to not just bring things to life, but fudge. Its really, really hard for 1st level basic characters to actually stay alive in, say, the Caves of Chaos from B2. Its hard for 2nd or 3rd level characters to stay alive, for that matter.
 


If you go old school...as the DM, you will have to not just bring things to life, but fudge. Its really, really hard for 1st level basic characters to actually stay alive in, say, the Caves of Chaos from B2. Its hard for 2nd or 3rd level characters to stay alive, for that matter.

First level can even be deadly for PCs in D&D 5e. When I ran The Lost Mine of Phandelver, I very nearly had a TPK with the very first encounter (i.e., the goblins on the road). Admittedly, I would have followed the book's instructions and just had the goblins leave the party unconscious if they hadn't won the fight.

But yeah, that's not a terrible reason to reconsider an OSR game. The main reason I suggested one is because I feel it might be better equipped to handle the type of imaginative play an 8-year-old would think of. Some more modern games tend to go along the lines of, "There aren't rules for how you can do that, so you can't," whereas OSR is more like, "That sounds awesome! Roll for it!" Admittedly, 5e can handle this type of rulings-over-rules play pretty well, but it still feels a little more rigid.

Still, 5e is a great way to go, and I'm sure the OP's nephew would be thrilled with it because it's Dungeons & Dragons (i.e., it has the name brand recognition).
 
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I'll also say 5e. Pathfinder is probably a bit too rules heavy for a novice player. Meanwhile, the 5e Basic rules are free, and the starter set seems at least decent. Also,it's currently in print, so easier to find than the older editions. Now, if the kid's just playing, edition isn't as important if the DM is any good. I've been running a 2e game for my sister's kids recently because it's the only edition I've got any published adventures for. I'd hardly consider it an ideal edition for novices, but things haven't gone too badly because the players can get by not knowing the rules inside out in the classic editions, while I'm still pretty familiar with 2e and I know how things work.
 

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