At a special preview of the film, Amitabh Bachchan said the film reminded him of the difficult time he spent as an actor in Calcutta, and asked for the film to be narrated to him.
The music that plays whenever the characters Girish (Sanjay Dutt) and Lolita (Vidya Balan) see each other is a short passage taken from the song "Ek Ladki Ko Dekha" from another Vidhu Vinod Chopra film, 1942: A Love Story.
Vidhu Vinod Chopra was initially unhappy with Saif Ali Khan's casting in the role of Shekhar, believing he was not a strong enough actor. However, after Saif and Pradeep Sarkar insisted, Chopra realised he was a perfect choice.
Vidya Balan was not the first choice for the role of Lolita. Vidhu Vinod Chopra was hoping for a well-known actress such as Aishwarya Rai Bachchan or Rani Mukerji. Vidya tested for the role for six months before Chopra was fully convinced.
Dia Mirza and Raima Sen had small roles, but they signed on to the film because they liked it and wanted to work with Pradeep Sarkar and Vidhu Vinod Chopra.
Vidhu Vinod Chopra was impressed by Pradeep Sarkar's music videos and asked him to direct the music videos for Mission Kashmir (2000). Five years later, Vidhu Vinod Chopra gave him a break to direct this film.
Vidhu Vinod Chopra stated that because he trusted Pradeep Sarkar's work, he did not sign cheques for the film's expenses and instead transferred the amounts to his own account. The cheques were to be signed by Pradeep Sarkar and his wife.
Howard Rosemeyer won the Filmfare award for best choreography for Kaisi Pehli. However, in 2005 the award was given to Vaibhavi Merchant for Kajra Re from Bunty Aur Babli, which caused controversy.