How to Roleplay Engaging Conversations


Yawn… Can I press the “skip” button on this quest giver’s spiel? Too often in tabletop RPGs, conversations between NPCs and the the players boil down to what we observe in computer RPGs: “Just give me the relevant information so I can be on my way.” In a roleplaying game, this interaction needn’t be so dull – and can, in fact, lead to some memorable moments in your game.

Here are four things you can do to produce more engaging roleplaying scenarios.

Give unexpected replies

Most interactions in our day-to-day lives aren’t engaging. Dialogue follows a flow of “prompt/response,” and as long as those responses don’t surprise us, the resulting conversation isn’t memorable. The information we learn may be interesting or useful to us, but the conversation is simply a medium through which that information is conveyed.

We can do better. We can make the conversation more than just a vehicle – we can make it a ride.

When we receive an unexpected reply to one of our prompts, our brains are forced out of autopilot. We already had in mind how we would respond to an expected reply; now, we’re challenged to improvise. If we’re thinking, we’re engaged. Consider the following prompts and responses:

Player: “How much for that sword?”

DM: “Pah! You think you can afford that?”


Player: “Well met. May the Holy Light bless you this day, priest.”

DM: “Huh? Oh. Right. And to you. May the Holy yadda-yadda… You get it.”

In both cases, the unexpected replies serve to characterize the NPCs being interacted with while providing prompts for a new conversation branch.

Add conflict

Conflict is the heart of storytelling. But conflict shouldn’t always mean combat, though it is the simplest example. Conflict arises when two or more parties are attempting to achieve mutually exclusive objectives. When engaged in a conversation, each party will attempt to steer the conversation toward its own objective, much like a tug-of-war.

Players generally engage in conversation in pursuit of a goal, be it to seek aid, information, or goods and services. But NPCs have goals as well. The priest may seek to convert the party to his religion. The merchant may be trying to offload a cursed sword that no one has been willing to buy. The innkeeper may be trying to keep shady characters away from his establishment.

This doesn’t mean that every NPC ought to be belligerent and uncooperative. An NPC who is either weak of character or doesn’t feel strongly about his goal will only offer minor resistance, and an NPC that is on friendly terms with the Players is more likely to be compromising and cooperative. Even partners can have mutually exclusive objectives; one may seek to destroy the villain, while the other may want to redeem him. In fact, it is this form of conflict — conflict among allies — that can lead to the most engaging roleplaying scenarios.

Interact with the environment

Fill your environment with objects, then interact with them. Conversations that engage the senses will force players to be more attentive. It’s easy to get lost in a purely cerebral activity like a verbal back-and-forth, but when you start to paint a picture by describing actions, you ground that dialogue in a physical environment.

The blacksmith hammers away at an anvil. The ranger sharpens his sword with a whetstone. The barkeep wipes a rag across the countertop. The bard plucks at her lute. The aristocrat leans against the hearth, gazing down into the fireplace. The priest paces the aisles of the church, lighting candles.

Pepper your conversations with actions to keep them dynamic. Set a stage, then use that stage to keep the players immersed in the scene. You’ll find your players following suit.

Know when to summarize

How do you ensure that all your dialogue remains engaging? Cut out anything that isn’t. A well-written novel wastes no words. Every line of dialogue serves a purpose, be it to reveal character, further the plot, or provide information, and a good author will ensure that all dialogue deemed important enough to be written is written in an engaging manner. But what about dialogue that isn’t deemed important?

Conversations that are either mundane or lengthy, such as purchasing rations at the market or a droning political exchange with an aristocrat, are best suited to summary. “You spend the next hour talking politics with Lord Lambert until you notice everyone else at the table has nodded off from boredom.”

Of course, if a player wishes to roleplay out a scenario and the result would be a net increase in fun for everyone at the table, then roll with it. Just keep in mind that some players are hesitant to summarize because they feel they must remain in-character at all times. Lead the example by knowing when to roleplay and when to summarize.

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Here’s an Example

Let’s put everything we’ve learned to use. In this scenario, the players are visiting a sage in order to acquire information about the villain. The resulting exchange could have gone as follows:

DM: “How can I help you?”

Paladin: “We’re looking for information about the Demon Prince Barunor.”

DM: “Ah, yes. Barunor resides within the third layer of the Nine Hells, where he presides over…” [Continues to speak, uninterrupted, for two full minutes, giving players all the information they need — and a great deal that they don’t. Within 10 minutes, the players have forgotten half of what was said.]

Paladin: “Uh, ok. We leave.”

Nothing there prompted roleplaying or asked for a conversation. We can do better.

DM: You find yourselves in the sage’s study, an impressive room that is half library, half museum. “Please, make yourselves comfortable.” Smiling, he gestures toward the numerous sofas and armchairs scattered around the room.

Paladin: “We prefer to stand.”

DM: For a moment, he remains frozen mid-gesture. “As you will.” He rises from the chair behind his desk and makes for a liquor cabinet, grabbing four chalices. “A fine elven wine from the highlands?”

Paladin: “We’re–“

Rogue: [Interrupting Paladin] “I’ll take some!”

Paladin: [Sighs lightly] “We’re here to learn about the Demon Prince Barunor.”

DM: His back to you as he fills the chalices, the sage noticeably flinches at the name, spilling some wine. “Barunor, you say? I’m afraid I haven’t heard of him…”

[The players exchange knowing glances.]

Paladin: “Please, there are lives at stake.”

DM: Carrying two of the chalices, the sage offers them to you. “Try the wine.”

Paladin: I don’t take the chalice.

Rogue: I grab it and take a big gulp!

Sorcerer: I take the chalice, smell the wine, and pretend to drink.

Paladin: “We were told you know about Barunor.”

DM: Chalice in hand, the sage paces around the room, stopping to run his hand lightly across the surface of a vase here, a creature’s skull there… “Were you, now? And I trust, of course, that you happened upon this information from a reputable source, rather than from, say, some dullard barkeep at a seedy tavern?”

Sorcerer: [After a pause] I hurl the chalice, pin him against the wall, and press my dagger against his throat. “Tell us everything you know about Barunor.”

[An Intimidate check is resolved; the player succeeds.]

DM: The chalice explodes into shards as it strikes the bookshelf, inches away from the sage’s face. He jumps in fright, the chalice falling from his hand and clattering to the floor, and then you’re upon him, sending the bookshelf rocking. Dust, scrolls, and tomes rain from the shelf. He stares at you, wide-eyed and quivering, “Pl-pl-please, I’ll tell you everything!”

Sorcerer: “Talk.” I press my dagger more firmly.

DM: He starts blubbering details about Barunor, his whereabouts, and the ritual needed to summon him. You learn that Barunor is vain, a master of deceit, and can be summoned by speaking his name while staring into a mirror soaked in calf’s blood. Are there any other details you’d like me to go over?

Paladin: [After a pause] That’s it for now.

DM: Okay. We can always go over more of the details later. The sage holds up his shaking hands in suppliance. “Pl-pl-please, that’s all I know!”

Sorcerer: I drop him to the floor.

Rogue: “Your wine sucks.” I splash the rest of it in his face and steal the chalice.

Paladin: “If you’re lying to us, we’ll be back.” We leave.

DM: Holding onto a pedestal for support, the sage gingerly rises to his feet as you leave and accidentally knocks over a vase. You hear him whimpering as you close the door behind you.

In this scenario, we gave the sage a secret objective: to serve Barunor, and thus withhold any information about him. But the players prevailed. Rather than just serve as an encyclopedia, the sage played a part in the story, has a personality, and hopefully contributed to the fun of the session. By adding a few minutes of improvised dialog to the game, we made a boring information dump into a memorable character who could reappear in a later adventure.

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