Sachin Kulkarni is a Mumbai-based mechanical engineering student who dreams of directing a film. A friend introduces him to cinematographer Anay, and with Anay's guidance, Sachin becomes an assistant director. Sachin's Marathi Brahmin family rents Jessie Thekkekutu's house upstairs; she comes from a conservative Malayali Syrian Catholic "Nasrani" family from Alappuzha, Kerala. Sachin falls in love with her the moment he lays eyes on her, but she is wary of talking to men around her strict father and initially responds with friction. Unable to hide his feelings, Sachin confesses his love, and she does not respond at first.
A few days later, his sister Shruti Bapna tells him that Jessie has gone to Kerala to visit her grandmother. He, along with Anay, heads to Kerala to look for her. After several days, he finds her and apologises. She introduces him to her family in Kerala as her “classmate.”
> "classmate."
Jessie denies she has any feelings for him but agrees to be his friend. On the train journey back home, the two grow closer and share a passionate kiss. Sachin is convinced Jessie loves him; the two meet several times, and Jessie begins to admit that she also likes Sachin but wants to refrain from any problems because she knows her father wouldn't give his consent for a Hindu marriage.
Consequently, due to misunderstandings between Jessie’s brother and Sachin, her parents learn of their supposed affair. They arrange her marriage with someone else and fix a wedding date. The day arrives, and midway through the ceremony, Jessie refuses to marry the groom, displeasing everyone in her family. Sachin, who had, without anyone's knowledge, come to Kerala to witness the wedding, is ecstatic and secretly visits Jessie at her home. She admits she has indeed fallen in love with him. Sachin later learns that she is married and settled abroad.
Two years later, Samantha meets him. She falls in love with him but is rejected by Sachin, who hasn't yet gotten over Jessie. He then comes up with a script for his first film, which happens to be his own love story. He calls upon [Samantha] as the female lead, and [Anay] as the film's cinematographer, and the film is eventually titled Jessie. While shooting for the film at the Taj Mahal, he sees Jessie, and she comes to speak with him. She admits that she is not married and is still in love with him, and he too says she is still in his heart. Sachin proposes yet again, and they get married the same day. This is revealed to be the climax of Sachin's film, which Sachin and Jessie in real life are watching together in the theatre. After the film ends, Jessie praises Sachin for his efforts, and he drops her home, implying that they have reunited.
