Vinnaithaandi Varuvaayaa (Will you Cross the Skies for Me?) is a 2010 Tamil romance film directed and written by Gautham Menon.The movie features Silambarasan Rajendar and Trisha Krishnan in the lead roles. The film, produced by four producers and distributed by Udhayanidhi Stalin, features a successful music soundtrack composed by A. R. Rahman, cinematography by Manoj Paramahamsa and editing by Anthony Gonsalves. The film's story was also simultaneously shot and released by Menon in the Telugu language as Ye Maaya Chesave with a different cast.

The film explores the complicated relationship between a Hindu Tamil assistant director, Karthik, and a Syrian Christian Malayali girl, Jessie. Karthik falls in love with Jessie only to be met by her indifference, behaving reluctant due to the fact that they belong to different religions and her strict conservative family will never consent to this. An unperturbed Karthik keeps asking her, she also falls in love with him. However, they have to undergo many problems and emotional conflicts; whether they can overcome all hurdles forming the crux.

The film, began its initial schedule in February 2009, following a mystery launch with a series of publicity posters being launched without details of the cast or crew. Shooting continued through 2009, with the film garnering significant media interest, through schedules in Malta and the United States. Prior to release, the film became the first Tamil project to have a music soundtrack premiered, abroad from India, with a successful launch at the BAFTA in London.The film, released on 26 February 2010, along with the Telugu version to advanced bookings worldwide. Upon release, the film achieved positive reviews, with several critics giving the film "classic" status, whilst also become a commercially successful venture. The movie has been declared as a blockbuster.

Karthik (Silambarasan Rajendar), is graduate in mechanical engineering in Chennai but aspires to become a filmmaker. Through his friend, Karthik gets introduced to a cinematographer, Ganesh (Ganesh Janardhanan). With the support of Ganesh, Karthik becomes an assistant director to K. S. Ravikumar. Karthik's family, who are Hindus, lives on rent on the bottom floor of a two storey house which belongs to Jessie's (Trisha Krishnan) family, a conservative Malayali Catholic Christian family from Alappuzha, Kerala, who live on the floor upstairs. When Karthik meets Jessie for the first time, he falls in love with her. Karthik expresses his love one day to Jessie, who is afraid of speaking to other men around her strict father's sight, and ends up angering Jessie. The two meet several times and Jessie begins to admit that she also liked Karthik, but wants to refrain from any problems because she knows her father won't accept a Hindu to marry his daughter. Her parents came to know about their affair and arrange a marriage for her. But at the wedding, she refuses to marry the groom, displeasing everyone in her family. Karthik and Jessie continue to love each other without the knowledge of their parents. Suddenly, Jessie is forced by her father to marry and seeks Karthik's help, who was in Goa for a film shooting. Karthik is unable to attend to her calls and messages as he was busy on the shooting spot and Jessie is unable to reach him. After a tense phonecall from Jessie, Karthik goes back one night to Chennai to check on Jessie. An angry and hurt Jessie makes a final decision to break up with Karthik because of her father's strong disapproval of their love. Later on, Karthik gets to know that Jessie got married and is settled abroad through his sister.

Two years later, Karthik meets Nandhini (Samantha Ruth Prabhu), who falls in love with him, but is rejected by Karthik who cites his previous affair with Jessie whom he could still not get over. He then comes up with a script for his first film, which happens to be his very own love story. He calls upon Naga Chaitanya as the films protagonist, Nandhini as the female lead and Ganesh as the film's cinematographer, and the film was eventually titled Jessie. During shooting for the film in New York, United States, he randomly sees Jessie again and she comes and speaks with him, they discuss their differences and both get married the same day and are happy again. But his meeting with Jessie is actaully revealed to be a scene in Karthik's movie. At the end of the viewing of Karthik's movie in the theater, Jessie and Karthik part ways, both with different lives and different destinies.