The Beginning of the Campaign and Roleplay Encounters

The party started out in a Tavern in the middle of nowhere on purpose. If they were out in the frontier, on the edges of civilization, the politics and beliefs of the world at large wouldn’t matter much. I just wanted to roll some dice. I also thought, as many new DMs do, that I could bypass the issues inherent behind the common words of advice, “Don’t just start in a Tavern.”

It’s D&D and I want to start in a Tavern, OK?

So there they started, in the village of Broken Gate, a trading center in a small colony of civilization on a largely untamed continent. A half-orc mercenary gets drunk and loudly engages the party.

“My spirit is light, but my pocket is heavy with coin! A round for everyone! Toast me – tonight we drink, for tomorrow we may die!

The half-orc introduces himself as Solomon, and he confides after many rounds that his fortune has been so good lately that he had to turn down a cushy job from the local Captain of the Guard. Turns out the Captain was offering gold in the hundreds for a simple job, simply hunting down an escaped prisoner that had run away into the wilderness. The nearby wilderness was sub-arctic, and winter was coming. The job, in truth, was likely nothing more than picking up a frozen body.

he half-orc introduces himself as Solomon, and he confides after many rounds that his fortune has been so good lately that he had to turn down a cushy job from the local Captain of the Guard. Turns out the Captain was offering gold in the hundreds for a simple job, simply hunting down an escaped prisoner that had run away into the wilderness. The nearby wilderness was sub-arctic, and winter was coming. The job, in truth, was likely nothing more than picking up a frozen body.

I should have just set all this up in a handout or a monologue but, me being me, I instead decided to insist on playing it out, every last inch of cringey roleplay at a time. Some of the players were inexperienced, they all didn’t know their characters yet. They couldn’t just slip into their shoes, and that’s fine.

Open-ended roleplay shouldn’t be thrust upon a new group, really, and especially not to open up session one. Focused roleplay, though, that worked, but we didn’t get there until the end.

The characters, of course, followed the hook. They got the job, from the Captain, who was a bit of a dick, and it was exactly as described. Bring him back either way, but a bonus if he’s alive so they can “make an example of him”. It’s the frontier after all, and order has a price. They scare off some other upstart adventurers from the job and went to investigate the Prison.

It turns out, a prison guard had helped the prisoner, Quindwin Davish, escape. The party tried to interrogate her, and she was uncooperative, opening up the first actual substantive roleplay question: What are we willing to do to get this information? The guard, Laria, was already wounded and hadn’t budged under physical interrogation, and although torture was briefly on the table, they ended up getting a few high enough rolls, a Cure Wounds, and some pointed questions in to determine the direction that Quindwin had run off in. I don’t know if they picked up on the romantic connection between the two NPCs, but if they did they certainly didn’t mention it.

Ranger rolls some dice, they travel. They track the prisoner to a freezing river, and then they reach the top of a waterfall. Below them, it lands in a half-frozen basin beside which lies two bloody bodies – one human, one animal. The ranger Althea, with her Elven eyes, see’s that it’s still breathing, but raggedly. Not for long probably. They try to quickly descend the cliff, they fasten a rope to climb down and, even with advantage, the Warlock rolls a 4 and falls. He lands with 1 HP, the Cleric and Rogue follow and help him up. The Wizard and Ranger stay atop on the cliff and see, from the treeline below, a pack of wolves attracted by the scent of blood.

This twist landed well. The party expected to track down the prisoner and have to fight him – I mean obviously, right? But they find him and it’s just a kid who was downed fighting a badger, and they find themselves needing to protect him to collect the full reward.

They kill the wolves, tie up their captive, and everyone makes camp. In the morning they decide to interrogate Quindwin – their “escaped prisoner” was a skinny red-haired kid, maybe 17 years old.

Sorry for the long intro, but this is what this little essay is actually about.

Quindwin tells the party, truthfully, that he was a guard before he was thrown in jail for refusing what he thought to be an unethical order, to beat up a gnome physician. The prison guard, Laria, freed him because they were in love. If he is returned to the village, they will both be killed.

Now, the party knows that the Guard Captain uses physical interrogation, having observed it on the other captive. The party also knows the Captain is kind of a dick and believes in using violence to enforce order.

Everything about Quindwin’s story tracks, and to anyone who believes he did the right thing by refusing an unethical order, by extension believe that he should not be imprisoned in the first place, let alone executed.

However, they also know that by willfully aiding or releasing their captive, they would be not only breaking their word but alienating the Captain – functionally the law of the land, as well as giving up their reward.

This is what I’ve started calling a Roleplay Encounter, and I’m really happy to have included it in my first adventure. This type of challenge encourages what I think is the best kind of roleplay. I’m not forcing the players to talk in-character or engage in any sort of theatrics, but instead making them engage with a problem the way their character would. I’ve given the players an ethical problem to which there is no Correct, or even Lawful Good solution, that their characters need to solve as a group.

The primary options presented to them are:

  1. Let their captive Quindwin go, and do something to save Laria, the captive prison guard, betraying their word and alienating the local authority. Chaotic Good.
  2. Keep their word, return their captive, and collect their prize. Lawful Neutral at best.

These options, and everything in between, were discussed by the players in character in what was actually a somewhat tense negotiation. In every way the social RP in the tavern failed, this succeeded. The players were forced to make a judgement based on what their characters value. Is it money? Trust and honor? Authority? Personal morality? Freedom? These all factor into the decision of what to do with the boy.

This is my first truly great D&D memory, and the moment where I thought I could actually be a decent DM if I kept at it. It all came together.

Althea, the Ranger, had an arrow pointed at the boy’s head. She was bringing something back, even if it was a corpse.

Gladomain, the Rogue, likewise wanted to tie him up and get on with the job.

Adrick, the Cleric, was advocating to let the boy go and negotiate a reduced punishment for the other prisoner. He would not condemn a good man to death.

They could agree that they didn’t want the prisoners to die, but they also didn’t want abandon a reward, or worse, become labelled criminals themselves.

Aemon, the Warlock, approached Quindwin from behind.

The other thing to take out of this anecdote, is that when I say that I gave the players a problem with no correct solution, I meant it. I, as a DM, had no idea what they were going to do in this instance. I had planned for them to go with Quin, to the east, I had planned a jailbreak of his sweetheart, I had planned for the party to cash in the reward and pick up another job. This simple cliffhanger, which I subjected myself to, was the start of my addiction to uncertainty.

The key to a good Roleplay Encounter is to present a problem where any solution you can think of has very real negative consequences. A choice between right and wrong is easy. A kobayashi maru is where the fun happens.

Aemon pulled out his dagger and slid it along the kid’s face. Quindwin cried out, “My ear!”

“Here, we’ll use this,” says Aemon, not a little smugly.

They had chosen the third option that I should have, but didn’t, consider: Lie and cheat until you make everyone happy. Chaotic Neutral.

“We’ll just tell the captain that he fell off this waterfall and wolves ate him. Perfectly plausible given the circumstances we found him in. The Captain must have an Arcanist or someone who can confirm this is actually Quin’s ear.”

Quindwin is openly sobbing now. The cleric heals him and the party shrugs and sends him on his way. “There’s a Druid circle nearby, they’ll give you sanctuary. Just follow my directions and you’ll find them.”

Time to head home and lie their pants off for gold.

The resolution was, although unexpected, fantastic. As dramatic as any outcome, and a brilliant display of player agency. More importantly, though, the players knew a little more about their characters and how they view the world than when they started the adventure.

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