The Art of the Sidequest, Part 1

I’m a busy grown-up with a job and a tie and everything, and so are a lot of the people with whom I game. And one of the problems with being a busy grown-up is that sometimes non-gaming obligations bungle into the way of game time. In the last month, we’ve had to cancel or nearly cancel sessions because we had a player working, being with family, going out of town, saving lives, or storming castles.

That part’s not a joke. All of those things happened.

Gamers are understandably loathe to not game. It’s in our name. But in situations where the game can’t progress because a player or three can’t make it our options are limited. We can either cancel the gaming session or have a session anyway, and then the question becomes how to deal with the missing player. I’ve offered a few suggestions before, but there’s a subset of options I hadn’t considered, namely to run a sidequest.

I’m going to assume you don’t know what that is because my spellcheck sure doesn’t. A sidequest is any quest that isn’t related to the main plot. For example, if you’re on a quest to save a prince kidnapped by a dragon and you have to fight some goblins because they’re guarding the path to the dragon’s cave, that’s not a sidequest because it’s a necessary part of working toward your goal. But if the goblins aren’t a problem you need to handle, it’s a sidequest. Even if killing them helps you because it means you can collect their bounty and afford that dragon-slaying sword to make the final fight easier, it’s still optional.

Which is the beauty of adding sidequests to a campaign. Because they’re optional, you can run them even when you’re short a player so that player doesn’t miss any of the main plot. Sure, the player might be miffed that they didn’t get to fireball some short folk, but they’re still fully caught up on everything that’s going on with the dragon. It’s better to miss a sidequest but still know where you are in the main plot than to miss a session and wonder why you’re hundreds of miles away from where you last remembered, alone, mostly naked, with swords pointed at you.

In general you’ll probably find you need sidequests more in long campaigns. So consider the timing of this post intentional.

There are a few types of sidequests you can use depending on what you need. In increasing order of campaign relevance:


  • Filler: A sidequest that has nothing to do with the plot at all. There are no long-term consequences, no rewards, no real threat to the party, and a very low chance that NPCs from the main plot will appear. An example is a video game achievement; you may get points on your profile or what have you, but the game itself doesn’t care whether you have an achievement or not. A filler session exists just to fill time and give everybody something to do, and it’s common to never speak of it against once it ends. In anime circles filler is almost universally reviled. But it can give you a chance to do something totally off-the-wall or non-canon, like try a weird game mechanic or throw a one-shot enemy at the party, and if you really want to game it’s better than nothing.
  • Graduated Filler: This is a session that masquerades as filler but gains relevance later in the campaign. For example, if you have a filler enemy who later shows up in the main plot, or if the place you visited in the filler session is the site of the final dungeon, the filler retroactively graduates to the main plot. Again with a video game example, this is an achievement that later unlocks something for you, like unlimited ammunition. From the DM’s perspective this roughly falls into two categories: innocuously important sessions, which look like filler to the players but in which you actually do something meaningful, or ascended filler, where you initially intended the session as filler and changed your mind later.
  • Proper Sidequest: A sidequest that affects the campaign but not necessarily the main plot. In video games most sidequests in RPGs are like this; finding all the treasure chests or killing the hidden boss doesn’t meaningfully change the plot but it does give you experience and loot you wouldn’t otherwise have. Arguably most sidequests in D&D are like this for the same reason. It’s a way of rewarding the players who can attend a filler session without significantly punishing the players who don’t. Sure, the present players might be a few hundred gold richer than those who missed a session, but at least everybody’s caught up on the storyline.
  • Main Quest in Disguise: A sidequest that’s actually part of the main plot even if it doesn’t look like it at first. Particularly irksome (I clearly have an opinion here) video games use these by offering sidequests but refusing to let you advance unless you complete them because they they provide some necessary reward. It’s a little iffy using these in D&D because you’re defeating the point of having a side session in the first place. There are two ways to go about it. The good way is to have something that looks distinct from the main plot but later ties into it; the goblins seem off the beaten path, but they’re actually the dragon’s minions and they’re guarding one of the artifacts the dragon uses to protect his layer, so now the party knows this and they can look for the rest. The bad way is to keep the sidequest unrelated except for the result; the party gets a magic scroll from the goblins, but it’s not clear why the goblins have it or what the scroll even does until twenty sessions later when it dispel’s the dragon’s wards.

The sidequest types are part of a balancing act, in that the earlier types are better for a player missing a session and worse for a player attending and vice versa. If a player is going to miss a session, they’d generally prefer if that session doesn’t include huge important plot information because they they feel like they’re missing out. But a player who did attend generally doesn’t want to feel the whole session was a waste of time, all risk and effort for no reward. Unless I’m running a breather session I try to stick with the middle two types for whenever somebody is missing and save the last for when everybody is there. This isn’t always feasible, like when a player can’t attend a session mid-dungeon, but it’s a good rule of thumb.

So that’s what a sidequest is and why. Next post I’m going to go over how and a few do’s and don’ts.

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