In television, there is a phenomenon of unexpected dance scenes in non-dance, non-musical texts. This article expands the currently limited research on this popular screen trope. Rich in dance and musical references, Apple TV+’s Ted Lasso (2020–23) presents an unexpected moment of dance in Season 2’s departure episode, ‘Beard After Hours’ (Season 2, Episode 9). I argue that the dance performed by Coach Beard (Brendan Hunt) further unfolds the series’ exploration of masculinities and mental health by expressing and producing my original concept of ‘pleasant pessimism’. Generated from Lauren Berlant’s notion of ‘cruel optimism’, pleasant pessimism resists cruel optimism and its fantasies of an unattainable good life, establishes acceptance of reality as is and offers an alternative way of being that is, however unintentionally, transformative. Merging this concept with gender studies and dance theory (primarily Laban Movement Analysis), I demonstrate how Beard’s dance into a world of pleasant pessimism expands masculinities and advocates for mental health through the production of (self-)acceptance. Ultimately, I argue, the moment of dance achieves the good life that is always out of reach with cruel optimism.