Tukukkk

For context, this is my first adventure as a DM.

About 40 minutes into the first session, while investigating the rumours about a ghost ship, the group meets with Aleyd Burrows, a skilled veteran, Captain of the Guard and a very important figure.

She gives them various pieces of information and sends them on their way with new leads. As the party starts to leave, the last player walks up to Aleyd, shakes her hand and tries to steal her purse. Luckily he passes the Sleight of Hand check with ease since he rolled a 16+8 (he's a rogue with Expertise).

However, I do not know how to deal with this had he failed.

Knowing him, he is likely going to pull similar stunts.

P.S. I did talk with him afterwards, and he promised to be more mindful from now on.

He enjoys fooling around, but he is trying to do so without reducing the fun of the others.

He also set off a bit of a conflict with another thing he did, which me and the other players commented on. He did thoroughly apologise for it, and they spent some more time talking it out.

I mostly want to know how to deal with deal with such situations without stepping out of the “in game” position.

This is not uncommon since many players come from video games, wantonly stealing and murdering NPCs. NPCs in roleplay games tend to be smarter though, and have logic.

Give them a reputational cost.

They didn't interact with anyone else. If they check their wallet after, they'll know that it was probably that thief who stole from them. So what do they do? Not fight a bunch of murderhobos. They go to the pub and complain about these so called 'adventurers' who rob and steal from everyone they meet, and then in that village or town, people refuse to serve that thief and anyone associated with them for fear of having their stuff stolen. Don't make it universal, unless they repeatedly do stuff, but if they harass NPCs, NPCs won't want to talk to them unless very seedy, and quest givers won't give them useful info.

If they had failed the check, the NPC would slap their hand away, swear at them, and march off to tell people how untrustworthy the adventurers were, unless she really really needed them.

Explain morality. Make sure they know being a thief doesn't mean they are supposed to steal from everyone they meet. Allies are supposed to be safe- just as being a fighter doesn't mean you stick your sword in random allies, being a wizard doesn't mean you turn the local cleric who heals you into a frog, being a thief doesn't mean random stealing.

Give them a common sense check. Sometimes it would make sense to steal from an ally. A sufficiently mercenary group might want to steal from an ally if there is a valuable enough possession, and that's a quest and a heist. If their ally has a rare and powerful magical item, maybe they can get it off them, and maybe it's worth the reputational cost. A few gold probably isn't worth that risk.

In a real situation, no one will ever try that. You talk with someone who can probably kill you in a second and you try to steal her purse ? No way.

This kind of issue can be from 2 things:

• The player test your limits and check if you are going to punish that kind of behavior


• Maybe the player was not really aware that Aleyd can kill him easily or just throw him into jail until the end of his life.

There's multiple kind of possibles punishment. Throwing the character into jail for years is the logical solution but the player will likely just make a new character.

Instead of this, you can :

• make Aleyd confiscate all the player stuff as a fine


• start a fight between Aleyd and the player. Of course the player's character can't win this fight but Aleyd does not want to kill him, she just want to make a fine and good scar on his face


• make Aleyd neutralize the player's character, then she says to the rest of the group: "You better look after him, one day you are all gonna die because of its fault"

Don't let the player derail things

Many players who are new to tabletop RPGs enjoy the feeling of liberty that stems from not being subject to a rigid mechanical engine, like in a computer game or a board game. This makes trying unconventional things like petty theft very appealing to some.

However, pulling off stunts like this detracts from an even bigger concern: a tabletop RPG is supposed to be something that you do together, as a group activity. Wanton theft and other troublemaking can quickly change the game from "a group of heroes adventuring together" to "Tuikku the Rogue stirs trouble and everyone has to fix it, every time". That's where approaches relying on in-game consequences fail --- even if you punish just the thief in question, and even if the punishment is fair, it still winds up drawing lots of time and energy from the entire group.

Therefore, as you've already opened conversation with the player in question, the next time they want to do something that'd potentially cause trouble for the entire party, say something like this:

Doing that would likely result in the rest of the session being spent to undo whatever damage or complications might happen. Given the magnitude of the decision you're making, I'm sorry but I'm not letting you do it unless everyone is on board.

(remember that everyone includes yourself. It's not something you should do lightly, but if you're uncomfortable accommodating for any player action, you have every right to veto them)

This has worked well for me beforehand --- the strong point is that it forces the player to consider the consequences of their actions on the whole game. Are cheap laughs or exercising their theft skills just for some coins really worth of half an hour of everyone's table time to resolve the incident and its aftermath? It's also flexible, as the same argument applies equally to murdering non-threatening NPCs and similar "rash" decisions.

Alternatives for sticky-fingered PCs

That said, if your player wants to maintain theft as a part of their character, you have options that don't require stealing the focus or risking the party at the table. One option is encouraging thievery as a Downtime activity, making the character earn some additional coin between adventures. You can ask the player to cover their crime sprees in a few sentences:

GM: "Ok, it's been four days since your last adventure. Do I remember correctly that Tuikku the Rogue was doing theft as a downtime activity? Roll how much money you made, and then briefly describe what you stole during that time, and from who."

Tuikku's player: "I mostly just picked purses in the marketplace from stuck-up burghers, and also swiped and fenced an ornate ring from a handsome gentleman."

If you feel the downtime action needs a little something extra, you can also drop in plot hooks:

GM: "This morning, you caught word that the gentleman has hired a large group of investigators to look for that ring --- for far more coin that the trinket is worth. They're roughing up people for information, and your fence has gone off the radar for their own safety. What's with that thing?"

You can also ask your player to come up with plot hooks or details of stolen items if you like.

this way, your player gets to engage in rampant theft and have that as a part of their character without it detracting from everyone else's sessions.

Actions have consequences

the last player walks up to Aleyd, shakes her hand and tries to steal
her purse. Luckily he passes the Sleight of Hand check with ease since
he rolled a 16+8 (he's a rogue with Expertise).

Before he rolled, what DC did you assign to the attempt? If you didn't do that ahead of time, then you are setting yourself up for difficulty in the future. The games basic premise is this (Basic Rules, p. 4):

1. DM describes the environment/situation


2. Player describes what they want to do.


3. 
   

   The DM narrates the results of the adventurers’ actions. (Only roll the dice when the situation is in doubt).

   
   
   

   What DC did you set for the attempt? In the basic rules (p. 61) we find:

   
   

Task Difficulty DC

Very easy 5

Easy 10

Medium 15

Hard 20

Very hard 25

Nearly impossible 30

If you set a DC of 22, and they rolled a 24 - fine! The rogue pulled it off. (See below). If you set a DC of 25, the rogue failed (24 being the roll+mods) and an angry Captain of the Guard is still shaking the hand of the thief and notices the attempt to steal her purse ... trouble just happened and needs to be resolved. Someone just made an ally into a enemy, or maybe not. Maybe some fast talking can get them out of this - "Captain, I was just showing you how good we are a this undercover stuff ..."

Will she buy it?

DMing note: you can always assign disadvantage to a roll for an ability check if the circumstances around it call for that. Is there a reason that you did not assign disadvantage to this blatant attempt at theft? You don't have to, but it seems a valid use of that mechanic.

The DM can also decide that circumstances influence a roll in one direction or the other and grant advantage or impose disadvantage as a result. (p. 60, basic rulse)

If the player didn't set up the situation such that the Captain of the Guard was distracted, the sleight-of-hand check will be a lot harder than if she was distracted. Use advantage and disadvantage as a DM. It's there for you to use.

Lastly, if you didn't first set a DC and the player "just rolled" and you all marveled at the high score, go back to the order of operations 1-3.

But heck, let's say "this rogue succeeded!" Nice pocket picking there!

The captain notices her missing purse

The game world reacts to the characters' decisions.

Either the Captain knows who she last had a conference with, and suspects that her purse is where they are, or, the Captain (your roll) does or doesn't remember who she was last in a meeting with when she knew where her purse was.

If you set it up as the latter case, or if you don't want to just decide, make an unmodified Intelligence Ability Check, or an Intelligence (Investigation) check on behalf of the captain. (I'd do it behind the screen ... DC 10 or so is suitable here).

1. If she misses the roll (your rogue need not know the outcome) she doesn't remember them in association with the purse and thinks she misplaced it.




2. If she makes the roll, well then, trouble for the rogue.

If the party gets a visit from the captain ...

... a squad of guards (NPC, Town Guard) armed with heavy crossbows, with the Captain leading them, tracks down the party (or just the rogue) and at crossbow point suggests that the rogue return the purse.

Further consequences are then figured out based on how the party responds.