After living through 50 virtual high school experiences and dating numerous virtual boys, Tomoko Kuroki feels primed to tackle her first year of real high school. However, reality hits hard as she discovers her introverted and awkward nature, a fact unbeknownst to her alone. With her dependable best friend Yuu Naruse by her side and the unwavering support of her brother Tomoki, Tomoko ventures into the unfamiliar territory of high school. Watashi ga Motenai no wa Dou Kangaetemo Omaera ga Warui! follows the journey of a socially awkward, somewhat isolated high school anime enthusiast as she strives to break down her internal barriers for a more fulfilling existence.