Ferdinand ‘Ferdie’ Pinto (Naseeruddin Shah), receives a letter in the middle of the night and realizes that his one true love, Stefanie ‘Fanny’ Fernandes (Anjali Patil), never knew about his true feelings for her. Angelina ‘Angie’ Eucharistica (Deepika Padukone), a young widow and a dear friend to Ferdie, decides to help him. Angie was married to Gabo Eucharistica (Ranveer Singh), who died suddenly[a] during the wedding party. Ferdie and Angie set out to find Fanny, with the help of Angie’s mother-in-law Rosalina ‘Rosie’ Eucharistica (Dimple Kapadia), an unsavory artist named Don Pedro Cleto Collaco (Pankaj Kapur) and Angie’s childhood friend Savio Da Gama (Arjun Kapoor). Savio was in love with Angie and has only recently returned from Mumbai, after leaving when Angie married Gabo, who was his best friend.
On the journey, Ferdie throws Rosie’s cat out of the window by accident whilst sneezing as he is allergic; so to keep her unaware, he retrieves the dead cat and pretends that it is sleeping. The group visits Fanny’s old house and find a deranged Russian man Vladimir Olianov (Mihai Fusu), who eventually tells them that Fanny sold him the house 20 years ago and moved to Tivoli. During the trip, Ferdie tells Savio that Rosie’s husband is not dead, but instead had run away to Madagascar with another woman, and Rosie had simply lied to the village for the sake of her pride. As they approach Tivoli, Ferdie thanks everyone for joining him on his journey – but unbeknownst to him, most of the other passengers have their own reasons for making the trip. Savio soon realizes that they have gone the wrong way, and are now in the state of Karnataka due to wrong navigation by Ferdie, who cannot read a map. When they run out of petrol, Ferdie volunteers to go and get some in the morning; so the group spends the night in the open field next to the road. Don Pedro tries to seduce Rosie into being a model for his painting, whilst Savio and Angie go away from the others to talk. Savio tells Angie that he does not have a big business in Mumbai as presumed, but rather he was a waiter for 5 years and is not wealthy. It is revealed that Angie only married Gabo because Savio never asked her, and she was in love with Savio as he was with her. He kisses her and she slaps him. They eventually talk and after realizing that they both still have feelings for each other, have sex that night.