‘Remember that time we…’ – How RPG encounters go sideways.

Role playing games are designed to be flexible and open-ended, and with a huge detailed world and an emphasis on player agency, anything can happen. It shouldn’t be surprising then, that sometimes what the Game Master has planned and what the characters do are very different things. I’m here to tell you about just such a situation, which turned into a true descent into lunacy.

I have been GMing a D&D 5e group through the Storm King’s Thunder official campaign. Needless to say, there might be a spoiler or two coming up.

Near the end of the adventure the players had been handed a gambling chip from a casino as a clue to the next story step. They had in fact visited this casino previously and recognised the chip. They knew where to go, and they knew they needed to ask the owner a few questions.

The casino itself is on a river barge in Yartar, that casts off at dusk and returns to the city around dawn. It caters to the upper crust of society, high lords and wealthy merchants, and offers all kinds of luxury and debauchery. In the hour before it leaves the captain hires commoners to work various jobs for the night and the head of security, a wizard named Pow Ming, welcomes guests, on the expectation that they are wealthy and unarmed. The adventurers had previously visited in various disguises, gaining access as wealthy guests, waitresses and musical entertainment.

The previous visit had been a whole session and I assumed that this one would be a quick in and out. They knew to dress up fancy, get the information and would not likely spend too much time revisiting the gambling games. How wrong I was.

The first problem was getting on board. I had unsubtly reminded them that getting on as a wealthy guest was the best option, and made a point of asking what they were going to wear. The monk and the ranger bought some slinky silk dresses; excellent. The bard planned to go on as musician again; good. The barbarian went to a tailor to commission some travelling clothes, and traded away a set of fancy clothes as payment; okay… The cleric used mending to patch the holes in his clothes; sigh. They did leave behind weapons and armour however.

At the boat the cleric, in his common travelling clothes, approaches the guest entrance and asks to enter. He receives a flat no. The barbarian steps up in his new travelling clothes, explains that they are adventures and had heard that “This was the place to be,” and receives the same answer. Imagine two randoms in hoodies and old jeans asking a suit wearing bouncer if they could enter the most exclusive night club in town. That is what they tried. No deception, no persuasion, no bribes. They just asked nicely. As they try to argue the monk and ranger strut up, hand a coin pouch to the security wizard and walk aboard.

Meanwhile the bard has engaged in a quick performance challenge to be hired over another applicant. The two rejected adventures walk over to the crowd of commoners and get themselves hired as rowers. The ship was propelled by thirty or so large oars in the bowels of the ship and that was where the barbarian and cleric were going to spend the encounter. Suffice to say, I had not fleshed out the rowing deck and its inhabitants.

The ship casts off and things progressed well for at least a few moments, with the ladies mingling in the casino, the bard playing away upstairs and the boys getting into the rhythm of rowing. One of the ladies, however, had not made it onto the boat last time, and decides this was the time to suddenly have a gambling addiction. I shuffle through my notes, find the details of the various games and spend way more time that expected gambling.

Eventually I had the chance to introduce the owner of the casino ship, a Lord Drylund, who was using the enterprise to build up wealthy backers for his plan to take control of the city. After a short description of him shaking hands and giving out gambling chips to his favourites, a comparison was made to The Godfather and I found myself doing a bad Marlon Brando accent. He progresses downstairs and crosses the room to greet the monk and the ranger.

By this point the ranger had decides she has no interest in anything other than gambling. Thankfully, the monk had her eyes on the prize. Having used up all her subtlety getting onto the boat, she proceeds to seduce Lord Drylund, with comments such as “My what a big boat you have” and “I bet your bed is just as big.” After choking momentarily on his drink, Lord Drylund eagerly escorts the two ladies upstairs, observed by the bard as they cross the dancefloor together.

Sensing that other players downstairs were feeling excluded, I give a bit of a description about how the barbarian is beginning to bulge out of his shirt and rip it open here and there whenever he gives a particularly strong oar stroke. The cleric decides to cast mending on it between his strokes, and it turns into a constant battle to keep the now sweat-soaked shirt together.

The barbarian starts to ask other rowers questions about Lord Drylund, so I let slip a few rumours, including the fact that he kept a pet octopus. The barbarian’s baffling response to this was to say “I suppose there is nothing wrong with that sort of thing, as long as the octopus is willing.” I react confused by this (half NPC, half DM) while another player snigger. The barbarian says that we had dirty minds, and it is just important “to have consent.” I lose it and break character.

On the top floor the monk and the ranger have just walked into Lord Drylunds cabin, where he does in fact have a large bed, as well as a desk, a small stove for heat and a large aquarium containing an octopus. The player playing the monk rolls a die, then looks at it with concern. She explains that due to her flaw being intense paranoia, and having had a rough encounter with an aboleth named Oosith (a giant intelligent squid monster), she had decided to roll a die to determine her reaction when she came across situations that might trigger her character. Her roll of two meant that her character would react badly, and she was torn about following her system when it would likely derail her own seduction plan. I told her I’d be happy with whichever she chose.

She sees the octopus and starts screaming. “An octopus? It’s one of his minions. Are you in league with Oosith? I thought he was a friend, but he betrayed me. Are you going to betray me? How far do his tentacles reach?” Lord Drylund, caught completely off guard, backs away. The ranger, who had come up expecting to do nothing more than play cards, distracts the monk by suggesting she draw a diagram of Oosith’s network, then finally gets to questioning Lord Drylund. She pushes him down to sitting on the bed, flashes her eyes red in intimidation (she is a tiefling by the way) and asks him about the gambling chip and its connection to the storm giants.

Scared as hell, Drylund confesses all. He is a part of the super secret Kraken society. He conspired with them to kill the storm giant queen and abduct the king. He is incapacitated on a boat in the trackless sea… Argh. Suddenly he clutches his head, screams and falls back dead. Blood runs out of his ears, nose and eyes. His kraken master telepathically heard him spilling the beans, and pretty much exploded his brains. The characters (and the players) don’t know this, however.

They are not in a good situation. Everyone noticed them walk this way arm in arm with Drylund. They are an hour into a twelve hour boat trip, with no way off but to jump into a deep, fast flowing river. The absence of the owner of the casino for almost the entire voyage would be extremely suspicious. They freak right out.

They drag the corpse into the bed and under the blood stained covers. The monk checks if his skull is intact (it is) and gets blood all over her hands. They wash it off by pouring wine over her hands and catching the result in a goblet, inadvertently turning the white wine into red. The ranger then splashes the rest of the wine over the bed and down the front of their dresses, because seeming really drunk would be helpful somehow? Now they will be infinitely more noticeable if they leave the room. The bard hears some muffled shouting through the wall and plays louder to disguise it.

At this point I decide to have a crewman knock on the door and call for Lord Drylund. They double down on freaking out. The ranger decides to jump into bed next to the dead Drylund. The monk whips off her dress and opens the door a crack. The crewman stops halfway through whatever he was going to say and find himself stuck staring at the gorgeous toned body of the monk. She explains that Lord Drylund is indisposed at the moment, and perhaps he should check back later. After a lingering look he turns to leave. The monk pushes the door closed, but before she can even breathe a sigh of relief, the ranger shouts out “Bring more wine!” to the retreating crewmen.

It was at this point I couldn’t help but break character. “Why on earth would you give him a reason to come back?” A look crosses the players face, like they only just realised what they had done. “I don’t know.”

At this point they just argue about what to do for a while. I check up with the other players. Down on the rowing deck, as characters they were unaware of the situation and as players they were sitting back enjoying the show. I point out to the bard that he is hearing some more commotion and he decides to finish his song then take a five minute break to investigate.

The crewman returns with the wine, and this time the tiefling strips down and answers the door. Confronted with the naked form of a bright purple devil woman with a long tail and small horns, he hands over the wine dumbly then retreats. The teifling puts the wine down on a table and goes back to failing at coming up with a plan.

The bard opens the door and surveys the scene. Blood on the sheets. Bloody corpse on the bed. Tiefling putting her wine stained dress back on. Monk looking about frantically. Heating stove, desk covered in papers, heavy curtains. The bard calmly opens the stove, grabs a flaming log and throws it on the bed. The other two catch on, one throwing papers around the room and the others setting the curtains on fire.

As soon as things start catching, the bard addresses his companions. “Okay. I’m going to head back to the stage and resume playing like everything is normal. You two wait a few minutes then run out yelling.” He leaves the room.

The other two stand around in a burning room. As it heats up I start rolling small amounts of heat damage, halved for the tiefling of course. After a few minutes and a few such rolls they decide it’s time. As they move towards the door I tell them that I had forgotten to mention that as they searched for combustibles a moment ago they did find a small wooden chest underneath the aquarium. There was really one there, it just hadn’t come up, and I only decided to mention it to see whether they would stay in a burning room for the promise of loot. I think you can guess what they did.

The ranger decides to try and open it then and there. With no thieves tools or any relevant proficiencies, she tries to force the lock using a fire poker and her strength of eight. I wasn’t surprised that she failed, but she was surprised when a poison needle trap jabbed her in the hand and successfully poisoned her. Now she had disadvantage on checks and attacks.

The monk steps forward and, after a quick discussion of possibly using dexterity instead of strength if she was trying to break the lock with her hand she rolls a critical fail. Even the dice were in on the chaos and she basically karate chops the poison needle still poking out of the lock, also becoming poisoned. Disadvantage for everyone!

The fire damage is starting to stack up so the tiefling says she will take the chest and hide it under her cloak, then insisting the monk take it despite having no way to carry it. Then they run out into the next room shouting about a fire. The bard instantly starts pointing out the exits and telling people to remain calm, as if she wasn’t the one responsible in the first place.

Screaming and running sounds then filter down to the rowing bay, and the cleric and barbarian rush upstairs. The come up on deck outside the casino. Through a large glass window they see their companions rush downstairs among a crowd of guests, while crewmen run to investigate the commotion. Seeing one of his companions carrying a chest the barbarian decides to smash the window and reach through to grab the very obvious chest.

A moment before this the magic wielding head of security comes around the corner to see what is happening. Through the panicked movement of the guests she sees one dishevelled guest pass a wooden chest through a broken window to a poorly dressed worker. She casts Hold Person on the burly man now holding the chest and he falls on his back, stiff as a board and still holding the chest. The monk vaults through the window, aware that she is the next target.

The ranger and the cleric, in no way implicated in the seeming robbery, instantly start attacking the oncoming crew members. These are level nine characters fighting bandit stat blocks, with their mighty 1/8 challenge rating. The cleric casts Spiritual Guardians which blasts three crewmen with 30ish radiant damage, but points out that he doesn’t want to kill them, he only wants to knock them out with holy fire.

The bard, seeing the head of security start to cast spells, decides to drop the safety officer routine and instead starts to act like a frightened old lady, grabbing the arm of the mage and shouting “Oh it was horrible!” to distract her.

Outside on deck the monk grabs the paralysed barbarian by his shirt and tries to pull him toward the bow of the boat. His new shirt, now sweat stained and torn apart by his rowing, tears completely off his body. Thankfully he shakes off the spell effecting him and is able to regain his feet.

Pushing the bard off her arm, the head of security looks at the monk and mentally implants the suggestion to go for a swim. Having already planned to jump ship, this works out well for her. The barbarian, seeing this development, decides to follow her over the rail, still carrying the chest.

The cleric and the ranger are not so quick to join. They hang around for at least a few more rounds, heroically beating up common sailors. Eventually they vault over the side and swim for shore as well.

Things wind down from there. The bard stays on the ship as the fire is doused and the conscious members of the crew turn around and sail back to the city. The characters each take turns trying to break the lock on the chest, but even the strongest fail. Eventually they meet back up out of town, where the bard uses his Chime of Opening to reveal a few hundred gold coins. They celebrate even this meagre haul, before one of them looks up and asks “Wait, did we actually get what we came for in the first place?”

As the encounter wraps up I am stunned. What I thought would be a quick in-and-out job, taking no more than an hour, turned into a chaotic comedy of errors that took up a whole five hour session. It was also one of the most entertaining sessions I have ever conducted, with a heavy load of roleplay and the slightest touch of combat.

What is the moral of the story? Is there one? Does there have to be? Perhaps not. Suffice to say that player agency is key, but is a double edged sword. Always be careful not to restrict the options your players can choose, but never think you can predict the choices they will make, especially in a high tension situation.

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