How do I cater to the Three Stooges and good roleplayers at the same time?

Question

As a little background, in case it matters: most of the players in my group (but not all) are college aged, and all of them are personal friends of mine. We're playing D&D 3.5. I myself am the group's only real DM, but even I'm more of a long-time listener than a long-time caller. I've been running roleplaying games for most of my life, but I've probably only run half a dozen real play sessions of any system as complex as D&D.

My group isn't currently playing because we're separated for work reasons. This gives me a little time to reflect before jumping back in.

So my players — let me tell you 'bout my players.

• The Barbarian loves D&D perhaps more than anyone else at the table. But he couldn't tell you just what a saving throw is. He tries, but he's got mild dyslexia, and hates reading almost as much as he loves role-playing. So he tries to rely on me/other players for the rules and plays a Barbarian because 'hit it with my axe' is always the correct solution. He's never once invoked his Barbarian Rage power.

• The Wizard is stunningly poor at thinking strategically. I have to practically bean him over the head out-of-character to remind him that he has the power to cast magic spells. In addition, he's so shy and non-confrontational that he can't even hold an assertive conversation with fictional NPCs.

• The Bard is super chill. No matter what happens, he's happy, because I gave him 500 bonus XP at the start of the campaign for drawing a picture of his character. And for pretending that all the other PC's are members of his delusional band. No problems here.

• The Rogue is the only player who I could say with confidence has read the rulebook. Many times, he's snuck off in the middle of the night to go use his Sneak skill, and the entire table (myself very nearly included) has sat in awe as he uses sheer brainpower to accomplish things the other party members never thought possible. There's no Munchkin roleplaying here, no Thespian roleplaying--just pure creative problem-solving.

• The Ranger (and elf Ranger, no less) doesn't seem to have grasped the ways in which D&D is different from a video game. He's a little frustrated because his character doesn't deal much damage with a default shortbow, but can't seem to make the leap to realizing that he needs to take some initiative if he wants to change that. I can't even get the guy to go shopping for a composite longbow.

So those are the regulars.

My question here isn't about the fact that most of them don't know the rules very well; I've more or less given up on forcing them to put in study time they don't want to, and instead choose to hope that over time, with gentle reminders, they'll pick up the rules they want to pick up and become pretty competent. This seems to have started working, to a degree.

My Problem Is:

How do I keep the game entertaining for this entire band of misfits at once? The Rogue is getting a little bored because no one else can keep up with him. He's asking me about a Ninja prestige class while I still have to walk some of the other players through leveling up their base class. The Wizard is getting a little discouraged because he can't keep up with the others. The Barbarian's fun times are interrupted every once in a while when he realizes that he could be doing things even cooler than hitting if he'd read a few more rules. The Ranger is just getting aggravated that his Ranger isn't a badass yet, and he's already level 3.

Over the last couple sessions, I once let the Wizard try his hand at being the DM. To make a long and depressingly bizarre story short, the party is scattered across half the fictional continent, and the party members who aren't in captivity are more interested in getting back 20K of 'Russian' gold than rescuing the others. I'm uncertain of my ability to bring everyone back onto the rails, because even getting them to finish a single dungeon is a major accomplishment. Even if I give them a map, they manage to get lost and conclude that they're supposed to exit through the nearest window.

You're free to tell me that we're playing this game wrong in every conceivable way. But please try to include an answer to the question as well if you choose to respond.

Answer 1

Well that sounds about par for the course. I have a regular group that I DM for since 2009, and your player archetypes sound pretty familiar to me. (And yes, those are the real archetypes, not what is described in the DMG).

Don't worry so much

First off, don't worry so much. From your post, it seems like it's going ok. The important part is that you have fun. If the group has fun, there's not a big problem, even if you as a DM might feel you are doing stuff wrong.

Talk about it

After a session, or maybe during a coffee or smoke break, ask the players about these topics. What do they like, what do they dislike? How do they think the game can be improved? If everyone says it's fine, great. If not, I am sure they have some suggestions for improvement. I do this after every session, sometimes for 3 minutes, sometimes we discuss this for half an hour or more. It really helps.

Play to the player's strengths

If a player or his character is good at something (and everyone has has a speciality), give him or her a chance to use this strength. So the rogue player is inventive - give him a chance to use his wits. What I do is that I generally prepare some specific additional puzzles or challenges for them. I think the best way to integrate those is if you have a fight and at the same time some additional pressing matter that people have to attend to, either with some skill checks or just with good ideas. So maybe while the party deals with the brunt of the attackers, someone must slip through the enemy ranks and disable the ballista before the city walls are down.

Help your players

So the ranger treats this like a video game, but is not pro-active enough. Well, he doesn't have to go shopping. Drop some loot for him that is a part (one third) of a magic bow. Maybe a bow string made out of dryad hair? This should awaken his video gamey instinct to collect all parts, involve him more into the story and finally lead to him getting a better bow.

Some answers on this board stress how important player agency and pro-active players are for the game. I am not sure I fully agree with this. Some people are just naturally more passive, and if you can help them so they have more fun and everyone has more fun, just do it.

Use mechanics to cover the player's weaknesses

For the wizard - maybe propose Sense Motive, Gather Information or similar (Insight in 5e) checks when you feel he's missing something. If he succeeds the check, give him a hint. Like this, you can use the character's strength to cover the player's weaknesses. And after a few successes, it is likely that the positive reinforcement will lead to the player doing this on his own more often.

A similar thing about this assertiveness: Have a friendly NPC cast a spell him, or maybe an enemy a curse, and tell him how this makes him feel more assertive, mighty and filled to the brim with power. Sometimes this helps such players to slip into a role they would not otherwise take on.

On the other hand, specifically this is not really a problem in my eyes - a nerdy shy wizard doesn't seem so out of place.

Offer help with their characters

So this is a two-sided sword. It might be a great help, but can also ruin a lot. Make sure the players want and appreciate your help with their characters before doing anything. You really want to avoid messing with 'their guy' if they don't want you to. But if done right, it can be a great help to certain players.

One of my players is like your barbarian player. Doesn't like to read the rules, but is very enthusiastic and a great addition to the game. Before a new campaign, I generally have a skype conf with him and discuss the background a bit and what character he wants to play. Then I build a character for him, send it to him and we discuss some changes he usually wants. Once we have a character he's happy with, I make him a nice colourful character sheet in Numbers with all the important stuff up front. This worked out very well. It allows him to focus on the game, and not worry about details or picking whatever CharOp stuff from way too many sources he's not interested in, while still playing his concept and being on a similar power level as other players who are more into optimising.

Allow them to rebuild or change characters (within reason)

Sometimes, a new player might choose a character that doesn't really fit his play style. Might be the wizard player would be happier with a sorcerer - new players tend to fare better with the simpler approach of having a few known spells instead of building a spellbook and preparing their daily prepared lists.

The system

Finally, maybe D&D 3.5e is not the ideal system for players who don't read up on the rules themselves. If your group is open to change the system, I can suggest two options:

1. D&D 5e. While similar in many respects, it has one advantage: A lot of stuff is just way simpler and easier than 3.5. While 3.5e is my personal favourite among all D&D editions, for my main group, I have switched to 5e, and we haven't looked back.

2. Games with far less rules: Dungeon World or Fate come to mind. I have played them, and had fun, but for my group, it was not the right choice. We like the miniature battles and everything around that. But those are certainly great games.

And, in the end, the evil master plan

Of course, all this cuddling and making players happy only serves one goal: to make them experienced enough so you can start being a true evil dungeon master. Once they know the system, know their characters and have a fair chance to survive bad things, the fun starts: Poison, traps and and horrible dismemberment. It's no fun punishing them if they have no chance to deal with it. But once they have shown they are up for the task, you can start driving the finger screws in, and let them into the tomb of horrors.

Answer 2

It's going to take a lot of encouragement to get the group into the frame of mind with enough knowledge of the rules to really grab hold of the reins and take control of your campaign, and the best way for you to do so would likely be to hold a rules primer for each of the characters that highlights each of the strengths of their classes and really lets them come into their own. You don't want to be mean when doing so, stay as helpful as possible while you're doing it to insure the maximum amount of receptivity.

I'd start with the wizard first, as wizards are naturally the most complicated of the classes you have present at your table and involve things much more advanced than move to x and hit y with your axe. You need to sit down with him and explain the ways that he can use his spells to maximum effectiveness. This should be rather easy, just collect his character sheet, see what spells he's taken, and present to him a few situations in which his spells could potentially be useful. The more knowledge he has about his spells the more likely he will be inclined to use them during combats or situations that can be solved by casting a quick cantrip.

The barbarian would likely be next. Dyslexia can be a problem and it does encourage people to not want to read, and you can help him out with that by reading the important stuff for him, make sure he knows about saves, about hit points, and most importantly instruct him on the mechanics for his barbarian rage and combat maneuvers such as trip, sunder, and bull rush. Once he realizes that his strong axe guy can become even stronger and hardier through an explanation of the rules he will be willing to hulk out and destroy his enemies, with massive damage numbers all around.

Lastly, Address the Ranger. He seems to have the smallest problem of the three, which can be fixed just by telling him the different rules surrounding ranged weapons and the differences between longbows, composite longbows, and mighty composite longbows. Explain to him that each of these individual weapons fires an arrow that flies faster because the bow requires much more than average strength to be able to pull back the string to launch the arrow.

Once he understands this and the way his strength modifiers work for damage perhaps take the time to introduce him to a prestige class with relaxed entry requirements, like Order of the Bow Initiate to increase his ranged damage to higher levels, as well as the Manyshot / Rapid shot feats so he can get the most out of his ranged class.

Once you've finished explaining this to the group you can use this actual learning and explanation of the rules as an ongoing part of your in-game narrative. Explain to each of the players that you were split across to the four corners of the world and that you each had to learn a special skill (Barbarian's rage, wizard's spellcasting, ranger's aim) before converging back on a single point to save the world from its ills. You can use this newfound knowledge as a campaign booster and hopefully motivate the more shy players to come out of their shells a little. They're among friends who will not judge them, and you should do your best to communicate that.

For the really good roleplayers give them a nice exp bonus once they do something particularly awesome. If the other players see you rewarding experience points for roleplaying perhaps it will encourage them to roleplay as well.

Answer 3

Knowing the Rules is mostly important for the GM.

I'm sure that title will attract downvotes, but it is important enough to put up there. As the mediator of the world, it is part of the GM's job to translate Player Action into Die Rolls. What you're running into here is a mental problem I should probably invent a name for so I can stop calling it the Three Clue Rule from that Alexandrian article - regardess, it goes thusly; from a position of knowing information, things seem simple, and attempts to explain it do not include enough detail or obvious simplicity to be understood by those who do not already know that information.

I've also put it like this; stop hinting, start telling.

-Your magical training tells you that you could use your Burning Hands to spray flame all over the kobolds, killing many of them in one fell swoop.

-This battle is going south, and you feel it coming over you, the BERSERKER RAGE of your ancestors. Do you let the hate flow through you, or control it?

-Your ranger thinks that while he is in town, he should probably buy a longbow rather than the hunting shortbow he currently has.. hrm. Maybe he can try to get his hands on a magical one? It would certainly help kill the larger monsters.

-These fools are gonna die if you don't do something, Bard! 'Like what' Use a mind control spell! 'I have those' Yes!

'I want to kill the kobolds' is a viable in-character action to state. It doesn't need to be 'I use my burning hands from SW corner of my square, aiming diagonally after moving 25' to the northwest' for you to offer them that, then if they say yes, move them and measure out a cone, and give them the dice to roll. Some players don't want to, or can't, interact with the rules. It's the GM's job in those circumstances to mediate the rules in the exact same way you mediate the world descriptions and NPC interactions - telling the PCs what is there, what they can do, and offering suggestions to shortcut the process.

Encounter Design

When you have a party with wildly different levels of skill and optimization, designing encounters that they can all interact with is important. Interactable terrain (rope bridges, moving carts, stairs to fight up, multiple levels, a burning building, clotheslines/hanging clothes, even just furniture etc), multiple foes including weak ones whose organization and manner of dress and weaponry tell a story, 'strong' foes that don't just rely on lots of damage and hp, but some kind of videogame-like defensive method (movement, defensive spells with specific timing-based weaknesses, AC, walls of fire, calling forth more minions like a leader or a summoner type, etc), foes that talk and reveal motivation and characterization by doing so, etc, these are all things anyone who has seen movies or read books can deal with, whereas 'a cockatrice' is more of an unknown quantity they will hesitate before trying to interact with.

Character Strength

I give bonus feats to weaker characters. And cool plot interactions. And have stuff there for them to kill. A weak character can be due to a weak class, a player bad at fighting/tactics/rules, or just an unlucky one. If you don't set things up for them to be heroic, and when I say set up, I don't mean 'secretly put a thing in there for them and tell no-one and don't make it explicit', and I don't mean 'OH HERE IS A RIDDLE ONLY A WIZARD CAN SOLVE'. I mean set up a believable encounter or problem their character can trash, set on fire, watch it explode, then pose in front of the explosion. And make it so it is right there and super obvious. Is this necessarily easy, no, but screw easy you're GMing roleplaying games. This can be as simple as adding some mooks to the fight in an annoying position so the wizard can ash them out of the way for the barbarian to rush up the steps and king hit the shaman before he gets off the ritual, or it can be as complicated as adding an evil Spymaster as an archenemy who exists throughout the entire game to rival your party's Rogue in epic backstabbery plottery goodness, and who the rogue fistfights atop a waterfall at the end of the campaign, both of them falling to their deaths.

Straight up giving mechanical bonuses to weak characters isn't ideal. It's better to mold the world around them to make it more likely they can be a hero too. But in extremity, it's better than having them feel impotent and useless.

TL;DR - Handle rules for people, don't tell them how the rules work. Design interesting encounters to hook their minds on the cool stuff they are doing, and quietly handle the mechanics for the ones who don't like the mechanics.

Oh, and as for getting the party back together, let me indicate my answer to this question. I'd suggest daisy-chaining it - 'hey Jim, how DID your barbarian end up in the Greenblood tavern two weeks later?' 'Bob, your Wizard arrived there roughly the same time - why was he on that road?'.

Keeping the party on rails isn't super important. What's important is understanding that to a certain degree you can and should use coincidence to make your story work. Why do all these fell powers suddenly appear as soon as these PCs start adventuring? Because if not, you'd be playing for a bunch of different characters 200 years later.