At the end of the fourth session, just yesterday, I actually ran out of content for the session almost an hour before I thought I would.

So I'm going to employ the old 'Adventurer's Guild' trope to present some space filling side quests. Problem is, for the main arc to keep making sense, all the side quests have to take place within a day's walk of the city. I've got a couple standard ones sketched out. One session length, gold payout at the end, boring if you ask me, but it's probably what they're hoping for.

What I'd like is to make an obviously boring 'joke' quest that ends up being several sessions long and takes several bizarre, hard left turns. I can write crazy crap all day, so I suppose my question is how do I present it to them?
How do I give them a quest that they're never going to take, until it's the last one on the list? And then when they finally do it they'll hate themselves for not doing it sooner.

If anyone has advice on getting my players to take the bait, I'd appreciate that as well as my main question.

  • \$\begingroup\$ I've edited your question to make it more easier to read. If you disagree, you can rollback the edit by visiting this link rpg.stackexchange.com/posts/166120/revisions \$\endgroup\$
    – Vylix
    Mar 10, 2020 at 4:18
  • \$\begingroup\$ This is a good subjective question that can utilise actionable advice based on analogous experience. \$\endgroup\$
    – Akixkisu
    Mar 10, 2020 at 14:51
  • \$\begingroup\$ To expand on Akixkisu's comment, this should be answerable and I don't think it needs to be closed until it proves itself to be attracting opinion based answers. \$\endgroup\$
    – Someone_Evil
    Mar 10, 2020 at 15:29

1 Answer 1


Quantum Reward

Make every quest they take is not your intended quest (or at least not the intended reward).

You mention your intent is to troll your players 'to hate themselves for not taking it sooner'. This is usually because the reward of the quest is very good or the impact of completing the quest will significantly help the other quests, so make it that any quest they take would yield rewards, but this one.

For example, there are three quests on the board.

  • Gathering herbs should reward a magic wand
  • Eliminate a pack of owlbear should reward a helm of true seeing
  • Delivering an urgent package should reward favor with the mayor, which would help them immensely - you want to hide this reward.

Suppose they pick Gathering Herbs as their first quest. All good. But then they pick Delivering Urgent Package as their second quest, which is not in our plan. Then you only need to swap the reward: Delivering Urgent Package reward now is helm of true seeing, and Eliminating Owlbears is favor with the mayor.

Whatever their pick, their 1st and 2nd quest always give reward other than favor with the mayor.

This is railroady, but necessary to achieve your goal. Why? Because the players can't be guaranteed to pick the quests in 'correct order', even when you know your players. Your players might be a serious group and do not like simple 'gathering herbs' quest, so you make 'gathering herbs', 'investigate the caved in goldmine', and 'investigate the haunted lighthouse', fully expecting 'gathering herbs' be picked last, but then they decide to take a break and want simpler quest.
Or meme-y group, like mine, will pick weird quest first.

Remember that not all players are okay with quantum choices, so tread carefully and be prepared to explain if ever they found out you are 'cheating' them.

  • \$\begingroup\$ If they pick the troll quest first, that won't ruin the quest, or my plan, it just wouldn't be as impactful a lesson. Rather I'd be impressed. But you have given me an idea: Maybe I can achieve my goal here by beating a cliche to death. This is helpful, thank you. As you can probably tell I struggle with communication in all forms, so I need all the help I can get. \$\endgroup\$
    – Jon
    Mar 10, 2020 at 4:03

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