Do you like the content I create? Consider buying me a coffee or purchasing one of my DMs Guild supplements. Every cent puts me one step closer to making TTRPGs my full-time job.

Each week, I sit down with five wonderful players (and sometimes a guest player) for our weekly game of D&D. After recapping the events of the last session, we do a roleplay warm up: a question that each player must answer on behalf of their characters. They can do this in character, or they can simply answer the question in their own words.

Roleplay warm ups have made a huge difference at our table. We love to explore our characters, bringing them to life through social encounters, challenges, and decisions. Though we’re not actors by trade, these questions help us to “get into character.” They prompt us to think of our characters as real people. What are their hopes and dreams? Do they have a favorite food? What do they do when they aren’t adventuring?

At the end of it (usually around 5-10 minutes max), the players choose someone to receive inspiration for their answer. I try to frame the question for any given week around the session I’ve prepared or its major themes. For example, if the characters were heading to Candlekeep, I might ask them something like, “If you were an author, what would be the title of your first book?”

Improvisation is hard. It takes practice, vulnerability, and a willingness to fail. Regardless of the size of your table’s audience—it’s okay if it’s just you and your players—you might benefit from adding a roleplay warm up before each session.

Roleplay Warm Ups

Below, you’ll find a running list of roleplay warm up questions that I’ve asked on Twitter (@justicearman). Please feel free to use them in your games.

  • In your character’s opinion, what quality should EVERY adventurer have?
  • What would your character say to the party with their dying breath?
  • What’s one errand your character has to take care of the next time they’re in town?
  • What is the best meal your character has ever eaten?
  • You’re at the Tipsy Lobster, a tavern in giant glass bottle that hugs a rocky shore-cliff. A spunky halfling in a blue doublet arrives to take your order. What do you tell them?
  • What is the best gift your character has ever received?
  • What is one title your character has earned that makes them proud?
  • What is your character’s retirement plan?
  • Your character stands at the front gate of Candlekeep, the Castle of Tomes. However, you can’t get in until you provide the monks with a rare book or piece of writing. What did you bring?
  • With which school of magic does your character most identify?
  • What is your character’s favorite thing about adventuring?
  • For what would your character sell their soul?
  • What did your character last dream about?
  • What is one thing your character prefers to do alone? (don’t be gross please)
  • What is one thing your character has changed their mind about?
  • When is the last time your character was cold to someone else?
  • When is the last time your character failed?
  • Does your character see the mug as half empty or half full? Also, what’s in the mug?
  • Is your character a clean person or a messy person?
  • What does your character do on their day off?
  • How would the other party members describe your character?
  • What song would your character sing at karaoke night?
  • What is your character’s pet peeve?
  • If your character had a warning label, what would it say?
  • What is one of your character’s fondest memories?
  • What is one rule your character never breaks?
  • A new adventurer approaches your character, asking them for wisdom. What lesson does your character impart to the young adventurer?
  • Describe one of your character’s childhood friends.
  • If your character could ask an all-knowing entity one question, what would it be?
  • If your character was an animal, which one would they be?
  • Where was your character educated? If they didn’t have a formal education, how were they taught?
  • What is one secret the rest of the party doesn’t know about your character?
  • When was the last time your character said, “I love you,” if ever?
  • What is your character’s catch phrase?
  • When’s the last time your character has used a set of tools?
  • What deity does your character worship? How do they show their devotion?
  • Tell me about one trinket your character possesses.
  • What is one thing your character admires about someone else in the party?
  • How does your character relax after a hard day’s work?
  • What does your character see when they look in the mirror?
  • If your character was an author, what would be the title of their first book?
  • Describe your character’s personal hell.
  • What’s one thing that always makes your character smile?
  • What is one way that someone can earn your character’s trust?
  • What is one thing your character has seen or done that no one would ever believe?
  • What is one goal your character hopes to accomplish in the next year?
  • What is something your character does every morning?
  • What does your character look like when they get angry?
  • What is one sacrifice your character has made?
  • Describe your character’s aesthetic in one word.
  • Your character is given a magic hourglass. With it, they can change one decision they made in the past year. Which one do they pick?
  • What’s one thing your character does when no one is around?
  • How would you describe your character’s fashion style?
  • What is one way that your character shows they care about someone else?
  • What is something your character doesn’t have enough of?
  • If your character was a drink, what would they be and why?
  • How can someone new earn your character’s trust?
  • If your character were to start a business, what would it be? What would make it special?
  • What is one thing your character has seen or done that no one would ever believe?

Like this article? Consider supporting me by buying one of my products on the DMs Guild, such as Darkhold: Secrets of the Zhentarim or Elminster’s Candlekeep Companion. If you’re running Baldur’s Gate: Descent into Avernus, consider picking up an alternative introductory adventure to the campaign, Devil’s Advocate: A Guide to Infernal Contractsor Baldur’s Gate: City Encounters.

You can also follow me on Twitter at @justicearman or sign up for my email list, the Gjallarhorn, for exclusive updates, playtest opportunities, and discounts.