It occurs to me that as I go forward trying to make the systems I've created to run a thief job duet game for my partner into something other people can use, it would be wise to come up with some guiding principles. Or at least, make concrete the ones I've been implicitly using.
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Crook
A game where a lone scoundrel does unusual jobs for unusual people.
1. Player-focused preparation. There is only one player; the GM should focus on things -that specific- player is likely to be interested in.
2. Alternative challenges. There is only one player; it is not possible to solve every problem by hitting it.
3. Alternative consequences. There is only one player; removing them from play should be avoided, but bad things can and will happen to them.
4. Rulings over rules. In the OSR/DIY sense: don't use a rule where you can make it work well on the fly.
5. Be permissive. Yes, and/but. No locked doors without stakes.
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Thoughts on what these mean for making decisions when designing Crook:
1: What sorts of things is our crook going to be interested in? The people who offer them jobs, and the nature of those jobs (I've been working on a job generator for this). The people and things that can help them accomplish those jobs. Something that they can do or work towards with the rewards from those jobs (are they paying off a debt? are they atoning for their past? do they want to prove themselves to a specific person? this likely should be a key trait established in when the player makes their crook). Organizations they can be part of, influence or be influenced by that will affect the other things they're interested in (thieves guilds, town guard, noble families, merchants, gangs, etc).
It's also important to tailor to the specific tastes of the player in your duet. Do they like dungeoncrawling more than courtly intrigue? Do they run off their mouth and start fights? Have they trained for years to become the perfect silent assassin? The jobs they're offered and the challenges they face should reflect the tastes of the player-as-a-person.
2: Combat shouldn't always be avoided, but there should be a focus on solving problems in a way that doesn't get the crook killed or incarcerated. This is important in all kinds of roleplaying adventure games, but I feel it's especially important in a duet. Ingenuity, insight, and non-linear thinking can be encouraged by giving the crook non-combat tools: immovable rods, vials of grease, and 1/day misty step as opposed to flasks of alchemists fire, acid arrows, and enchanted daggers (though if such standard combat items are given sparingly, that will encourage their use in creative ways).
This also can be reflected in environment design. Firey laterns swinging on long chains; precarious boulders above the narrow pass; loose bricks around the other side of the house. Traps that can be reset or redirected. Multiple paths in and out, and ways to manipulate the environment totally--what if there's a button on a pedestal that turns all the liquid in a 20 ft radius into blood? What if the inscription on the ceiling, when translated, teaches a chant that blocks out the sun for 2 minutes and then you forget the chant forever?
3: Preventing your one player from doing what they want to do by killing them or otherwise taking them out of play only serves to stop the game. Instead, have things break, or lost, or be stolen. Have important other people die. If a brutal combat does occur, have the crook be scarred or lose a limb or an eye. Or perhaps the baddies choose not to kill: it's always fun to have our protagonist hogtied and left to die in the desert--or perhaps thrown into a barrel, which is then chucked into a river heading toward a waterfall.
4: This is as much a reminder to myself to pare down rules wherever I can as it is guidance for running the game. That said, while making systems for Crook, I can and probably will go overboard, with full knowledge that I'll have to cut away all the cruft later. A rule of thumb I like for this is from Goblin Punch: "only write a rule when it is better than what you could come up with on the fly". And "better" can be defined in a number of ways as detailed in that post.
5: Others have been far more sophisticated than I with this, but nothing annoys me more than a locked door that is hard to open and if you fail there's no consequence other than not getting through the door. At least put some time pressure on: is the guardian automaton searching for the crook? Is a boulder rolling down the hallway towards us? Or give consequences for failure: the lock breaks and now you've made a wall. Or picking it sloppily triggers a visible blowdart aimed at the lock, or releases acid into the font of healing mineral water you're trying to get to. NO LOCKED DOORS WITHOUT STAKES.
If they want to do something and there's no consequence for failure, they do it! If you really want it to hurt for your Crook to try doing something mundane you can roll to see how many tries it takes and make them lose some spare change down a chasm each time they stumble (and I hope it's clear that that kind of pettiness is precisely what should be avoided). This goes for -abstract- doors especially. If our crook has a hunch about what kind of liquor the gang leader likes to drink as a digestif, they either can find out by asking the GM if they know or can do something interesting to find out (like sneaking into the leader's office and reading their diary, or bribing the manager of the member's-only bar, or beating it out of a lackey)--it should -not- be locked behind a knowledge roll that can be failed.
I think that'll do for now.
OH WAIT one thing I like about the name Crook is that it reminds me of "by hook or by crook" which is exactly the way in which our protagonist should try to accomplish things.
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