Ulv stumbled through the snow covered trees. He’d been stripped of his weapons and shirt and was given a pouch of herbs to crush and smoke when he felt the time was right. Apparently, they were supposed to give him some sort of vision about what  his test was. 

“This is the craziest thing I’ve ever done,” Ulv grumbled to himself amid strides through the knee deep snow. He needed to find shelter soon. There was no way he’d survive if he didn’t get out of the blowing wind and snow. 

As if in answer to his mental request, he spotted a cave up the slope of the hill he was climbing. The cave was almost covered with snow, but had an opening large enough for Ulv to enter. 

The interior was cold, but less so than the freezing forest outside. It was dark, but some light reflected in from the outside snow. Ulv made his way as deep in as he dared without a torch. The cave was much deeper than he’d anticipated. That meant more warmth but less light. 

So what would you like to do?

Intro

One important thing you’ll want to remember is that for the most part, these questions work when asked to specific individuals. Singling them out can help to get a better response from some of the more unresponsive players. Just make sure that the question is set up the right way. In fact, before we begin with the actual questions, let’s talk about a few requirements for a good NPC roleplaying-prompt question.

1. Purposeful

You can’t just ask random questions and expect that  every question results in better or more roleplaying. For each question, you need to have a specific purpose. Maybe you ask an open ended question to allow the player more freedom and creativity. Or maybe you ask a very specific question designed to get the player to actually respond.

1. Player directed

The best questions are focused on specific players. If you ask questions directed at the party, it is very likely that the person who is most used to roleplaying will respond. Getting a player to respond who rarely roleplays requires direct questions. That’s not to say that every single question needs to be focused on stimulating roleplaying. Some questions are just for the sake of the story.

Now with those two question requirements in mind, let’s get to the actual questions of today’s show.

What do You Think?

When directed at a specific player, “What do you think?” can be a very powerful tool to help re-engage a player who may have lost focus, or just help jumpstart the party into helping everything collaborate. I’ve used this with ally NPCs or even some NPCs that are slightly adversarial, though I haven’t ever used this question from the standpoint of a complete villain. I haven’t really found a scenario where that makes sense. Simply ask this question using the character’s name and voila! They have to respond with at least something. Even if they say, I have no idea, they’ve at least said something! That is a win in my book.

What’s Your Story?

I find this question works the best when it’s an NPC that is somewhat neutral to the party, like a shopkeeper or something. Naturally, the party will look different compared to the normal customers (usually), so a shopkeeper could take interest in the party, if only to hear a new story. You can also use this question from the point of view of an NPC traveling with the party. The only drawback with that is once the question has been answered, that’s it. If it didn’t lead to more roleplaying, you can’t really ask it again from the same NPC.

That’s a nice piece of equipment, where’d you get it?

This question is very similar to the previous question. From the point of view of NPCs, most of the equipment that our adventurers have is really nice and shiny. Normal folk rarely have opportunities to encounter the types of magical items that adventurers carry. I also like this question, because it has an obvious answer. Any roleplay shy character can give an easy answer as to how they acquired a particular item because rather than having to make up some answer on the spot, they can just respond by recounting the history of the game. Anyone can do that.

How’d you all meet?

Remembering that these questions work best when directed at a specific character, this question works well because like the previous question, it’s simply a matter of recounting history. It’s also a good question if the campaign has been going on for a long time. It’s nice to remind your players where you all began the adventure and how far you’ve come.

Why’d You Become Adventurers?

This question works best in one-on-one settings, like two people keeping watch, or a player walking the town alone during a shopping session of D&D. You might have to warm up the player to get the optimum roleplay experience. Thinking of a deep question from their backstory like this one might be too much right out of the gate. I would maybe warm it up by commenting on how difficult the road has been thus far and pointing out some of the foes that have been faced. Then the question can be breached about why the particular character became an adventurer in the first place.

What are Your Goals?

This question is hugely helpful for the Dungeon Master looking to add in story arcs that deal with a particular character’s backstory. Like the previous question, if the table is generally dominated by one or two roleplaying geniuses, then it’s better uses in a one-on-one scenario. This question will give you, the DM, a lot of ammo for preparing future twists and turns in the story. It can also help you fulfill on promises to each player. Each player will want a specific experience, even if they don’t know it. By asking what the characters want, you’ll be better able to fulfill on those promises. 

Become a Roleplaying Master

Using these questions can help, but the best thing to help your players roleplay more is to work on your own roleplaying. By leading them with the example of a Dungeon master who isn’t afraid to be the tavern keeper, the villain, or the strange drunk on the side of the road, your players will feel more comfortable themselves getting into character. So loosen up and start practicing. Take every session as an opportunity to improve. Your players might not react right away, but soon enough, they’ll realize just how much fun it is and they’ll join in the roleplaying.

If you think I missed any questions, let me know by going to Instagram at Betterdungeonmaster.

We’ll be back next week with another amazing episode. Until then, let’s go ahead and roll initiative.

Mentioned in this episode:

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