What Makes A Roleplaying Game Interesting: Lessons For DMs

The problem with roleplaying games is that we dungeonmasters steal all of our best plot points from books and movies.  And no wonder!  We loved seeing Frodo sneak his way to Mordor, loved seeing Luke flying down the trench of the Death Star.
The problem is, “Luke flying down the trench of the Death Star” can make for a terribly boring gaming session.
“Okay, you’re flying down the trench.  Darth is behind you.”
“I fly up and out of the trench so he doesn’t kill me.”
“You can’t.  You need to fly in a straight line to keep your target in sight.”
“I… shoot at Darth?”
“You have no rearward facing cannons.”
“I… dodge?”
“That’s a good idea!  He shoots at you… (rolls)  He misses.  The force is strong with you!”
“I shoot at the exhaust port.”
“You’re not in range yet.”
“Well, I guess I fly forward.”
“Okay, Darth shoots at you… (rolls)  This time he hits!  Artoo goes up!”
“Are there any tactics I can use in this situation?  Any way of bettering my position?  Any relevant choices I can make aside from keep flying in a straight line and get shot at?”
“Um…. no.  You’ll be at the exhaust port in five rounds.  Hang on, and Darth rolls to hit…”
“Wake me up when I can do something.”
See, too many novice dungeonmasters think that exciting roleplaying is generated from situations and stakes. Which is a natural mistake; if you’re not paying attention too closely, that’s what the best stories look like they’re about.
So a lot of dungeonmasters steal from a movie and say, “Well, the Dark Overlord is rising from his pit!  The world is at stake!  He’s surrounded by a hundred of his minions, and the players must kill the minions before he wakes!”
Then the characters play whack-a-mole for twenty rounds, endlessly rolling the same dice to “kill another minion, kill another minion, kill another minion” and the game is now reduced to what the dice say instead of what the characters do.
The trick to DMing is realizing that situations are only useful so long as they set up interesting choices – then fast-forwarding past all the parts that don’t involve the characters making interesting choices.
Because when a character in a movie has no interesting options, that creates tension, because we’re not that character.  We worry because the character is helpless, and we want them to get out.  But when we are the character, and we have no interesting options, that creates a mixture of frustration and boredom, because we want to do something to propel our character to safety, and yet we’re told that we are helpless.
People don’t like going to games to be helpless.
Likewise, having big firefights in a movie looks like fun, because it passes quickly and the character is stylish.  But if it’s a curb-stomp battle where the DM will not say “Okay, it’s clear you’re winning, so you mop up the remaining five mooks,” then eventually the characters realize “Oh, yeah, I have to roll an 8 or above to kill a mook with my best attack to end this tedium,” and the game degenerates into rewarding dice rolls over creative roleplay.
(Some mooks will argue that a good player will always find a way to make the game interesting. This is partially true. However, a DM’s job is to make the game entertaining for everyone, not just the top-tier players, and why should I work that hard to have fun when the DM should be on my side?)
From a player’s perspective, the trench run is interesting when Luke decides to turn off his targeting computer and trusts to the force.  It’s interesting if Han (the character) decides to fight his way to the Death Star and save Luke’s ass.
It’s not interesting when Luke is locked into a single tactic – fly straight and pray – and we have to endure that for five rounds of dice-rolling.
Your players show up because they want to make interesting choices.  So:

• Do not present them with false choices: “Oh, I guess you can sneak into this castle!  But I don’t like the idea of you sneaking, so I’m going to punish you for not talking your way in like I’d planned.”
• Do reward them for making interesting choices.  You don’t have to have them succeed.  But interesting failures can be more entertaining – see also, Han charging after the small group of stormtroopers, only to run into an entire squadron of them.  Don’t fail; escalate.
• Do not give them combats where the most effective tactic is “use this weapon again.”  Mix it up!  Find a way to make them devise new tactics!  (And if the only tactic that will work is “the tactic you had in mind,” refer back to “Don’t present them with false choices.”)
• Do fast-forward whenever possible.  If the characters would make no interesting choices here, summarize.  Yes, Luke has to fly another 140 kilometers in this trench, which would technically be five rounds, but what’s better – five boring rounds, or one totally exciting one?

Your whole goal as a DM is to give the characters interesting choices.  You want to have a battle with eight mooks?  Great!  Do that!  But don’t have the characters stand in an empty hallway, trusting to dice over tactics.  Take a hint from Raiders of the Lost Ark and have the battle take place in a bar, which starts burning, with lots of cover and lots of creative things to use.
Because remember: “Being surrounded by 1,000 goblins” sounds like it should be fun, but you don’t have a lot of choices here.  “Having to stand on the bridge and tell the Balrog that he shall not pass”?
That’s the choice.