Mazes & Mondays: Unfortunate Side Quests
The Chronicle of Unfortunate Side Quests
Every game master has been there. You carefully craft a dramatic storyline, and then one innocuous side quest derails everything. The hero’s solemn vow to defeat the ultimate evil is put on hold… because they’ve discovered a badly injured talking bird that needs their help. What starts as a minor detour balloons into hours of absurd chaos. This is the magic of side quests, and when they go off-track, they become the stories your players will laugh about for years.
This guide will explore how to craft side quests designed to spiral wildly out of control. We’ll share hilarious examples, provide practical tips, and offer three 2d6 tables to help you create unforgettable chaos in your next game.
Why Side Quests Matter (Even the Ridiculous Ones)
A great side quest can bring unexpected depth to your game. It can uncover obscure parts of the world, develop relationships with quirky NPCs, or simply provide a much-needed comedic break from heavy plotlines.
Unfortunate side quests, however, have a charm all their own. These are the ones where a single decision snowballs into catastrophe. They’re hilarious, inconsequential, and utterly outlandish, but they also keep everyone invested and engaged. Done right, an unpredictable side quest can become the highlight of any campaign.
Case Study of Chaos
Picture this. The party visits a small fishing village for supplies. A local elder asks them to investigate why the fisherman aren’t catching what they used to. Seems easy, right? But one harmless role-playing moment introduces a clumsy apprentice wizard who accidentally animates an entire fleet of fishing boats. Now, the players are scrambling to wrangle possessed ships while trying to avoid angry villagers. The fishing problem? Still unresolved, thanks to all the property damage.
These disasters remind us that sometimes the messiest side quests are also the most memorable.
Crafting Wild and Wacky Side Quests
Follow these steps to intentionally design side quests that threaten to go gloriously off the rails.
1. Start with a Simple Premise
A side quest doesn’t have to be complicated. It often begins with a mundane problem, like “fetch a rare herb” or “help fix a broken well.” What makes it spiral is layering chaos on top of this mundane prompt.
Roll on this table for Side Quest Premises (2d6)
| Roll | Premise |
|---|---|
| 2 | A goat has wandered off and must be retrieved. |
| 3-4 | An NPC needs help evicting a mischievous creature. |
| 5-6 | A local festival has gone terribly wrong (but how?). |
| 7-8 | A wandering minstrel is searching for their missing lute. |
| 9-10 | A merchant claims their wagon was robbed by ghosts. |
| 11 | A strange, glowing object fell from the sky overnight. |
| 12 | A child swears their imaginary friend is real. |
The key is to keep it small, enticing, and deceptively simple.
2. Introduce Unexpected Twists
Once the players take the bait, start pulling the rug out from beneath their feet. Maybe the herb they’re collecting loves to teleport away when approached, or the “ghosts” robbing the merchant turn out to be extremely clever raccoons armed with glitter bombs.
The more absurd the twist, the better. Aim for surprises the players could never predict, but that still feel consistent within your game world.
Roll on this table for Absurd Side Quest Twists (2d6)
| Roll | Twist |
|---|---|
| 2 | The quest giver reveals they lied about why they needed help. |
| 3-4 | The quest item talks and is extremely rude. |
| 5-6 | A magical storm erupts, but only in a 20-foot radius. |
| 7-8 | The “enemy” turns out to be a misunderstood ally. |
| 9-10 | A rival adventuring party arrives to “help” and makes it worse. |
| 11 | A completely unconnected NPC accuses the players of sabotage. |
| 12 | The problem has already escalated into full-scale chaos. |
3. End with Over-the-Top Consequences
Finally, capitalize on the chaos by letting events spiral into increasingly ridiculous consequences. Perhaps rescuing the cursed goat (finally!) reveals it’s actually the village mayor. Or maybe the players’ bumbling leads to a parade of angry squirrels taking over a nearby tavern. Consequences cement the absurdity and leave everyone laughing.
Roll on this table for Consequences of the Side Quest (2d6)
| Roll | Consequence |
|---|---|
| 2 | The entire town now worships the players as minor deities. |
| 3-4 | An innocent bystander is accidentally crowned king of something. |
| 5-6 | A rare, mythical creature shows up out of nowhere. |
| 7-8 | All mundane objects within a mile radius temporarily come to life. |
| 9-10 | The players unknowingly set off a completely unrelated crisis. |
| 11 | A festival is held in honor of the players’ “heroism.” |
| 12 | The quest giver vanishes, leaving behind only cryptic notes. |
Tips for Running These Quests
While chaotic side quests can be fun, they still require thoughtful handling. Here are some best practices to keep things manageable (and enjoyable):
- Balance Humor and Impact: Sometimes the ridiculousness can overshadow the main story. Tie effects or consequences of the side quest loosely back to the greater narrative to retain focus.
- Read the Room: Not all players enjoy utter absurdity. Gauge your group’s mood before pushing the chaos dial to 11.
- Roll with Improvisation: Your players will inevitably add to the pandemonium. Lean into their ideas whenever possible to make the experience collaborative.
Why These Side Quests Shine
Unfortunate side quests remind us why we play these games in the first place. They bring laughter, creativity, and spontaneity to the table. Whether it’s a cursed goat causing havoc or an accidental festival in the players’ honor, these moments become the memories you talk about for years to come.
Game Masters, don’t shy away from the chaos. Use it to your advantage, and make side quests an opportunity for hilarity and connection. After all, an unfortunate detour is often the most direct route to an unforgettable adventure.
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