That Moment When is a comedic, interactive digital series starring actor, writer, and improviser Milana Vayntrub, known for her quick wit, grounded humor, and memorable roles across television and online media. The series places Vayntrub at the center of a playful, choose-your-own-adventure style narrative where audiences guide her character through a series of awkward, chaotic, and hilariously relatable life moments. Blending sketch comedy, improv, and audience participation, the show showcases Vayntrub’s signature charm and comedic timing in a uniquely immersive format.
Across its episodes, That Moment When pushes the boundaries of digital storytelling by involving viewers directly in the story’s progression. Each choice leads to new scenarios—from cringey social encounters to unexpected twists—highlighting Vayntrub’s ability to adapt, react, and build comedy in real time. The interactive structure not only elevates the humor but also emphasizes the universal truth behind the title: life is a collection of moments we stumble through and laugh about later.
Beyond its entertainment value, the series further solidifies Milana Vayntrub as a multifaceted performer with a strong connection to online audiences. Already widely recognized for her comedic roles, viral presence, and social advocacy, Vayntrub brings sincerity and spontaneity to the project, making the viewing experience feel personal and delightfully unpredictable. That Moment When stands as a fresh, modern spin on episodic comedy—one that celebrates audience engagement, embraces imperfection, and turns everyday awkwardness into something joyfully cinematic.
