Whiskey Bear’s Big Adventure | A Learn to Play D&D One-Shot

Whiskey Bear’s Big Adventure | A Learn to Play D&D One-Shot

A beloved talking dog is kidnapped! Team up to rescue Whiskey Bear in a whimsical, beginner-friendly D&D adventure full of heart and humor.

TYPE

One-Shot

LEVELS

1

LANGUAGE

English

EXPERIENCE

Beginner

AGE

All Ages
3 NEEDED TO START
$10.00

/ Session

Details

Once / Friday - 11:00 PM UTC

Mar 13

Session Duration / 2–3 hours

0 / 6 Seats Filled

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This game will begin once 3 players have joined
About the adventure

Whiskey Bear’s Big Adventure is a Learn to Play Dungeons & Dragons one-shot designed for brand-new players, families, and anyone looking for a fun, low-pressure introduction to tabletop roleplaying. Set in the cozy town of Timberwick, the adventure begins when the town’s most beloved resident—a talking Bernese Mountain Dog named Whiskey Bear—suddenly goes missing. Players take on the role of level 1 heroes hired to track down the kidnapped pup. Along the way, you’ll explore a charming small town, meet quirky NPCs, solve simple problems, and learn the basics of D&D step by step. The story is lighthearted, whimsical, and full of heart, focusing more on creativity, teamwork, and imagination than complicated rules or intense combat. This game is taught in a friendly, learn-as-you-go style. I’ll explain rules as they come up, help guide choices, and make sure everyone feels comfortable asking questions. No prior D&D experience is required—this adventure is built to be approachable, encouraging, and fun for first-time players. I offer two versions of this adventure: a family-friendly session, where children are welcome to play alongside a parent or guardian, and a separate adults-only session for players who want a slightly looser, sillier vibe. Both versions keep the same cozy tone and beginner-focused approach, just tailored to the group. If you’ve ever wanted to try D&D—or share it with your family—Whiskey Bear’s Big Adventure is the perfect place to start

Game style

Roleplay Heavy

Combat Lite

Organized Play

Puzzle / Mystery Focused

Rule of Cool (RoC)

Meet the Game Master

5.0

(19)

Streamer
LGBTQ+
Neurodivergent
Artist
Cosplayer
Women/Femme Identifying

Less than a year on StartPlaying

104 games hosted

Highly rated for: Creativity, Inclusive, Sets the Mood

Average response time: 2 hours

Response rate: 100%

About me

Hi, I’m Skyybunny – your go-to DM for unforgettable campaigns and one-shots! Whether you're craving a wild romp through a dragon’s hoard or an emotionally charged battle with world-ending stakes, I specialize in crafting fun, fast-paced, and cinematic games. I’ve run countless games for players of all experience levels, and my passion lies in making epic high-level play accessible and exciting without the overwhelm. Expect tight storytelling, dramatic moments, tactical combat, and just the right amount of chaos. Looking for an adventure with big stakes and even bigger laughs? You’ve come to the right place. Let’s roll some dice and make some memories.

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Character creation

Creating your character

To keep the focus on learning and having fun, pregenerated characters will be provided for this one-shot. These level 1 characters are designed to be easy to understand and great for brand-new players and kids, letting everyone jump straight into the adventure without feeling overwhelmed. Players who would like to create their own character are also welcome to do so, either before the session or with guidance at the start of the game. Starting Level: Level 1 Stats: Standard Array Hit Points: Max HP at level 1 Ruleset: D&D 5e (2014 or 2024 supported) Sources: Official content available through D&D Beyond If you choose to make your own character, I’ll provide a D&D Beyond campaign link with access to the sources needed. I’m happy to help explain options, suggest classes, and make sure everyone feels comfortable with their character. This game is about learning, creativity, and teamwork—not optimization—so no prior D&D experience is required.

What to expect

Preparing for the session

Players will need to join the Discord server, which is where voice chat, communication, and coordination will take place during the session. Owlbear Rodeo will be used for maps and visual aids no download is required. For family-friendly sessions, children are welcome to play with a parent or guardian present. For safety and moderation purposes, players under 18 will not remain in the Discord server after the game concludes, as the server includes adult conversations outside of sessions. No prior D&D experience or additional software is needed; just come ready to have fun, ask questions, and help save the best dog!

What Skyybunny brings to the table

My GM style is friendly, patient, and focused on fun. I embrace the Rule of Cool, encouraging creative ideas and imaginative solutions over strict rules mastery, especially for new players. I’ll provide a variety of pregenerated level 1 characters for players to choose from, complete with tokens so everyone can jump straight into play without stress. If players want help understanding their character or abilities, I’m always happy to explain things as we go. Expect cute, easy-to-read maps and whimsical background music during the session to help bring the world to life. Combat is light and beginner-friendly, with a focus on storytelling, teamwork, and learning how D&D works rather than on tactical complexity. My goal is to create a welcoming, low-pressure environment where players, especially first-timers, feel comfortable, supported, and excited to play.

Homebrew rules

Homebrew Rules: These homebrew rules apply to all of my campaigns and are designed to keep the game cinematic and fun without bogging things down. Potions: -Drinking a potion yourself is a bonus action -Feeding a potion to someone else is a full action -If you take a full action to drink a potion, you regain maximum healing Critical Hits: -On a critical hit, damage is maximum dice + rolled dice Initiative Twist: -Rolling a natural 20 on initiative lets you choose turn order positioning for yourself among the party Carry Weight: -I don’t track carry weight unless things get silly Spell Components & Ammunition: -I don’t track spell components or ammunition (unless it is a specific type)

Equipment needed to play

Internet

Computer

Microphone

Safety

How Skyybunny creates a safe table

Creating a safe, welcoming environment is a top priority—especially for new players and family-friendly games. Before the session, I’ll share a brief Lines & Veils overview so players (and parents or guardians, if applicable) know what content to expect. This adventure is designed to be lighthearted and age-appropriate, and I’m always happy to adjust content to suit the group’s comfort level. During play, players can communicate boundaries or concerns verbally or via private message at any time. I regularly check in throughout the session and will immediately pause or redirect if something feels uncomfortable. Questions, uncertainty, and requests for clarification are always welcome. After the game, I’m available for aftercare and check-ins, whether that’s answering questions, talking through moments from the session, or helping new players feel confident moving forward. My goal is for everyone to leave the table feeling safe, respected, and excited to play again. Guardian Expectations (Family-Friendly Sessions) Children are welcome to participate with a parent or guardian present for the duration of the session. Guardians are asked to remain available and engaged to support their child, help with focus if needed, and assist with any questions during play. For safety and moderation reasons, players under 18 will not remain in the Discord server after the session concludes, as the server includes adult conversations outside of game time. These guidelines help ensure a fun, respectful, and age-appropriate experience for everyone at the table.

Content warnings

Safety tools used

Frequently asked questions