In her first film of the millennium, Kapadia co-starred in Farhan Akhtar's directorial debut "Dil Chahta Hai" (2001), which depicts the contemporaneous, routine life of Indian affluent youth, and focuses on a period of transition in the lives of three friends (Aamir Khan, Saif Ali Khan and Akshaye Khanna). Kapadia played the role of Tara Jaiswal, a middle-aged alcoholic woman, an interior designer by profession, and a divorcee who is not allowed to meet her daughter. The film presents her story through the character of Siddharth (Khanna), a much-younger man whom she befriends and who falls deeply in love with her. Kapadia said making the film was an enriching experience and called her part "a role to die for". Critics lauded "Dil Chahta Hai" as a groundbreaking film for its realistic portrayal of Indian youth. The film performed well in large cities but failed in the rural areas, which trade analysts attributed to the urban lifestyle depicted in it. Saibal Chatterjee, in a review for "Hindustan Times", noted, "Dimple Kapadia, in a brief, somewhat underdeveloped role, presents a poignant study of loneliness".