DMing for a 5th Grade Boy

Hello fellow DMs,

I recently mentioned that I play DnD to my 5th-grade cousin. He came over to my house this weekend, and we played the level 3 one-shot from the Candelkeep set of adventures. I had him use my level 5 Dragonborn Paladin character, since he was a solo player and just wanted to jump into a game. As we were going, I realized that the typical roleplay/mystery-based games I normally run were not up his alley, and he much preferred to fight things. I am going to finish up the one-shot with him today, and then see if he wants to play more.

If he wants to play more (which, based on how much he was telling his mom about it, I think he will), I am going to help him make his own character and start the campaign at level 1 to teach him about all of the typical DnD abilities and tropes. I plan to run some overarching plot that will get him to level 5, with boss battles at the threshold to the next level (I don't like XP-based leveling), but I need some suggestions on what the subplots for each level should be. I think he will be playing solo or with another cousin my age, so encounters will be a bit easier than normal.

I also want to use this as a chance to teach him about general RP table manners, so if/when he finds a bigger group to play with, he can be a good party member.

Any advice you have would be great!

Update: He wants to keep playing! He's going to play a human rogue, and I'm going to build his character sheet to make sure it doesn't get too overwhelming/unbalanced. I think a Pirate-based game should have a good opportunity for Plan-A-is-kill-people type of plots, lots of fun loot, and a good chance for NPC roleplay. Lmk your advice, and if there are any good oneshots I can start to build off of.

When playing with only one or two people, it can sometimes be difficult to keep them engaged, so try to keep the story moving and, based on his playstyle, don't delve too much into roleplay, keeping most conversations short and informative. A pirate adventure sounds awesome, some helpful sources can be Ghosts of Saltmarsh and the rules for underwater combat and boats in the PHB. 

Plot is kind of optional at that age. As someone who also started playing in 5th grade, a long, long time ago, we just did dungeon crawls. It was 1e, which arguably was mostly about doing dungeon crawls, but it was what we were really interested in. Mostly we just needed a reason to be pointed in the general direction of a dungeon and that was all the role play involved. 

But if you’re going pirate campaign, you can always do it island hopping style. They’re looking for, I don’t know, the One Piece. They go to an island, fight some monsters, take their stuff. The one piece isn’t here, so repeat. Then throw in an island or two that’s got a pirate town where they can buy supplies and have recurring NPCs and maybe have a quest giver in case the PCs aren’t sure what to do next.

You might also want to look at Tasha’s sidekick rules. Rogues really need someone in melee with them to help trigger sneak attack. Or build a DMPC that’s one of the tank-y clerics (tempest is great for a pirate) so you have someone who can be in melee and heal. 

I play with my kids often, and we started when the youngest was 4. I play a simple version with them and write adventures they are interested in. The rules are the most basic to still allow game play, somewhat akin to 1E. The games are short. 1 hour until recently when we played for two 2-hour sessions. I avoid difficult combat encounters although most of my combat encounters at my adult table require strategy to win.  I also minimize the risk of death (although character death is not infrequent at my adult table).  

I have been told by people on this forum doing the above is impossible but it works real well for my kids (and sometimes their friends).  

~V

I run for a table of 6 at my schools club so it about finding a chance of what you enjoy and what they enjoy

If you don't mind spending some money (about $5) DM's Guild has a great little adventure called The Crystaline Curse trilogy that I recently ran to help teach someone how to play. It's written specially for one DM and one player, goes from level 1-5, and is written very much as a tutorial with clear "now show me how you attack, now show me role play" sections.

(Just checked and it's free at the moment: https://www.dmsguild.com/en/product/279400/crystalline-curse-trilogy-bundle )