Haley Whipjack

She/Her

Haley Whipjack is a host and game master of TTRPG show Unprepared Casters. She is a fan of all things fairy tale, fantasy, and fanciful. They have been running games of Dungeons and Dragons for close friends and big names alike for over 6 years, including players like Brennan Lee Mulligan, Travis McElroy, and Spenser Starke. When they aren't playing TTRPGS or DMing, Haley is posting media breakdowns on YouTube, or teaching elementary school students at her day job.

Game Style

Haley runs games that are character-driven and rule-of-cool forward. Players at her table will be solving puzzles, thinking outside the box during combat, navigating complex social interactions, and dealing with the consequences of their in-game actions in ways they might not expect, but will always see coming in hindsight. If you like thinking about your characters small interpersonal interactions just as much as you like planning their gamebreaking mechanical moves, you will love her table.

Upcoming Events with Haley Whipjack

D&D in a Castle | USA | July 5 - 9, 2026

Ravenloft: The Horrors Within Launch Event

D&D in a Castle | USA

4-day immersive retreat

July 5–9, 2026

Thelien’s Rest (Mohican Forest, USA)
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D&D in a Castle | UK

4-day immersive retreat

October 4–8, 2026

Lothmere Castle (Darlington, UK)
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D&D in a Castle | UK

4-day immersive retreat

October 9–13, 2026

Lothmere Castle (Darlington, UK)
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Early Access

D&D in a Castle | UK

4-day immersive retreat

April 19–23, 2027

Lothmere Castle (Darlington, UK)
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