Don’t Be Shy! is a coming-of-age story about Shyamili Das, aka Shy (Aarushi Bajaj), a young woman living with her parents, Joy Das (Anurag Basu) and Jaya Das (Anju Alva Naik), in Mumbai’s Girgaum. Her parents run Shyamili Sarees, a struggling saree shop, but Shy is embarrassed by her middle-class upbringing. At college, she pretends to come from a wealthy family, claiming that her parents live in London and own an exclusive boutique. Shy is dating Mayank Jhunjhunwalla (Piyush Khati), the privileged heir to the Jhunjhunwalla Group of Companies and her college classmate. She has meticulously planned her future: she intends to secure an internship at one of Mayank’s companies, become its CEO within a decade, and eventually marry him after he takes over his family empire. However, her carefully constructed plans collapse on Mayank’s 21st birthday when he announces that he has no interest in joining the family business and instead wants to pursue a career as a singer. Shocked and disappointed, Shy belittles his ambition, leading Mayank to end their relationship. As she struggles to deal with the fallout, her lively friend Tara Verma (Bianca Arora) and childhood friend and neighbour Dhruv Kumar (Ansh Duggal) add to the fun, confusion and unexpected twists in her life.