One of my favorite things to do in more limber storytelling formats is to find a way to set and then subvert expectations. If you read my flash fiction, you’ve seen me do it tons of times. What you don’t know is that subverting expectations is my favorite way to create comedic situations in my Dungeons and Dragons campaigns. It is difficult to create humor without some about of subverted expectation because most humor is derived from an unexpected outcome to a pose situation. For example, the joke “Three men are walking down the street. Two of them walk into a bar but the third one ducks.” takes the format of a “walks into a bar” joke and spins it on its head, subverting the expectation that the punchline was going to involve a situation inside a drinking establishment. Of course, explaining a joke removes the humor, so the above joke is no longer the bit of supreme wit it was before I started this post, but it illustrates the quick payoff most jokes depend on. If you wait too long for the punchline, it is a lot more difficult to make the joke stick the landing.

In Dungeons and Dragons, though, the Dungeon Master has a little more leeway. For instance, in a comedic game I read a couple of weeks ago, the players were selected to participate in some kind of game by forces beyond their ken. As a result, they were pushed through a portal into a different world where they were given a problem to solve. In this case, they stepped out of a preparation room and into a Dr. Seuss world and were immediately approached by the Lorax who requested their aid in defending a grove of trees. Since all of the players knew the Dr. Seuss story, they immediately leapt to the yellow-mustachioed creature’s aid. They charged right up to the giant machine ripping up trees and woodland creatures as it belched smoke into the sky and accosted the man operating it.

As it turns out, he was just some guy doing his job. When the found out that the manager was in his operations booth off at the edge of what turned out to be a surprisingly rectangular forest, they went to discuss the problem with him, all the while animals continued to run into the now-idling machine. There, they found out that the company the manager represented owned the land and had specifically grown these trees to be harvested along with helping environmental groups restore the natural forests they had previously destroyed following the Lorax’s successful campaign to raise public awareness of the environmental impact of the loss of all those natural habitats. Unfortunately, this was the point when the party decided that the smoke was still a probably and started attacking the machine and its poor operator. If they’d continued seeking a peaceful solution, they’d have discovered that the smoke was actually beneficial to the environment given that the atmosphere of this strange planet in an alternate universe had a different chemical makeup than the atmosphere of earth. Instead, they attacked the poor operator, nearly killing him, and then actually killed the Earth Elemental cop who came to arrest them. After stealing a stun baton from one of the security officers and grabbing the badge the Earth Elemental dropped, they declared victory and then assisted the Lorax and his guerrilla army chase the rest of the company off the property before stepping through a door to their next waiting room.

Not only was this story itself a subversion of expectation (you should have seen their faces when I described the Lorax and his guerrilla fighters appearing from amongst the trees right after the Earth Elemental crumbled into rubble and a copper badge), but it’s part of a broader effort on my part to set the stage for future encounters in this “shiggles” campaign. I take something fairly simple and clear-cut, flip it on its head, and let them find out how far astray their assumptions have led them. After this, they’re generally a little more on-guard and I can actually break out the big guns. In a previous shiggles campaign, I had their characters wind up in a room that looked strikingly like the one they were in and, after the first remarks about how dumb it was that I was going that meta subsided, revealed that they’d actually stepped onto the elemental plane of Generic Suburban Houses that all contractors of pre-developed neighborhoods summon their houses fun. After that, they visited Carpenter’s Hell, and wound up accidentally stepping into a Harry Potter book before visiting a Faerie’s Demesne which was actually from a book none of them had read so no one got the reference.

The whole point of subverting their expectations constantly was to get them to abandon them completely so they would live entirely in the moment. If you can get your players to exist in that mental space, it is easier to keep them involved in the story you’re telling and the jokes you’re setting up. They stop worrying about what they should do or how they should behave and simply act, littering the campaign with easy places for you to insert humor or for it to arise naturally out of the group dynamic as they go about whatever little tasks you’ve given them. You need to keep subverting their expectations in order to maintain that mood, constantly flipping the script on them so they never feel like they’ve figured you out. If you stop or let things go too long, or maintain a joke for too long, then you step away from the comedy and back toward the drama of Dungeons and Dragons. For instance, my last “shiggles” campaign had a character all of the players loved, called Blornth the Tuba Player. Because they literally abandoned everything they were doing to follow him around, my ability to subvert expectations was pretty much limited to having Blornth do ridiculous stuff and that started to get stale quickly. I’m certain that, if the campaign had continued for much longer, they’d have all gotten sick of him and we wouldn’t be sharing memes about tuba players and musician gods while lamenting the end of the last campaign.

Comedy, like wisdom, needs to change and grow in order to stay fresh. If you stick with one thing for too long, it grows stale. So throw a curveball at them and, as soon as they think they’ve got you figured out, throw in a fastball just to watch them doubt themselves while trying to figure out were the trick is. It’ll be funny for everyone, especially you.