Karthik falls in love with Jessie the moment he sees her on the street in front of their house. Jessie is from a conservative Malayali Nasrani Christian/Syrian Catholic family from Alappuzha, who lives upstairs. Karthik's family, who are Tamil Hindus, rent the bottom floor of Jessie's house.

With Ganesh's help Karthik becomes an assistant to director. His friend introduces him to Ganesh, a cinematographer. Karthik is a Mechanical Engineering graduate in Chennai with poor results who aspires to become a filmmaker instead of an engineer. A short film/sequel titled Karthik Dial Seytha Yenn, again directed by Menon with Silambarasan and Trisha reprising their roles, was released in May 2020. It was later remade in Hindi as Ekk Deewana Tha. The film released on 26 February 2010, along with the Telugu version to advance bookings worldwide. Karthik falls in love with Jessie only to be met by her indifference and reluctance as they belong to different religions and her strict conservative family will never consent to their union. Vinnaithaandi Varuvaayaa explores the complicated relationship between a Hindu Tamil boy, Karthik Sivakumar, and a Malayali Christian girl, Jessie from Alappuzha, Kerala. Rahman, cinematography by Manoj Paramahamsa and editing by Anthony Gonsalves. The film features soundtrack composed by A. Before release, it became the first Tamil project to have a music soundtrack premiere outside of India, with a successful launch at the British Academy of Film and Television Arts (BAFTAs) in London.

Shooting continued through 2009, with the film garnering significant media interest, with schedules in Malta and the United States. Launched after a wave of publicity posters with no details about the cast and crew, Vinnaithaandi Varuvaayaa began its first schedule of filming in February 2009. The story was simultaneously shot in Telugu as Ye Maaya Chesave, starring Naga Chaitanya and Samantha, however, with a different cast. Madan under the banner Escape Artists Motion Pictures and RS Infotainment, the film was distributed by Udhayanidhi Stalin's Red Giant Movies. Jointly produced by Elred Kumar, Jayaraman, VTV Ganesh and P.

Will you cross the skies for me?) is a 2010 Indian Tamil-language romantic drama film written and directed by Gautham Vasudev Menon, starring Silambarasan and Trisha.

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