Vinnaithaandi Varuvaayaa explores the complicated relationship between a Hindu Tamil boy, Karthik Sivakumar, and a Malayali Christian girl, Jessie Thekekuttu from Alappuzha, Kerala.
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Vinnaithaandi Varuvaayaa introduces him to her family in Kerala as her "classmate".
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Vinnaithaandi Varuvaayaa learns that Jessie has decided to break up, as the relationship is not peaceful due to her parents' disapproval.
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Vinnaithaandi Varuvaayaa says she has agreed to marry a boy of their choice.
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Vinnaithaandi Varuvaayaa doesn't want Karthik to wait for her too long, as he has his dreams to fulfill.
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Vinnaithaandi Varuvaayaa falls in love with him, but is rejected by Karthik by saying that he hasn't yet gotten over Jessie.
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Vinnaithaandi Varuvaayaa then comes up with a script for his first film, which happens to be his very own love story and is shot in Tamil.
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Vinnaithaandi Varuvaayaa calls upon Naga Chaitanya as the film's protagonist, Samantha as the female lead and Ganesh as the film's cinematographer, and the film is eventually titled Jessie.
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Vinnaithaandi Varuvaayaa admits that she is not married and is still in love with him, and he too says she is still in his heart.
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Vinnaithaandi Varuvaayaa tells Karthik that they cannot lead a life which is full of obstacles as well as without parents approval and hence they depart separately, to lead different lives and different destinies.
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Vinnaithaandi Varuvaayaa marked the beginning of a collaboration between Rahman, Silambarasan and Gautham Vasudev Menon.
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Chennai Online said, Vinnaithaandi Varuvaayaa is an excellent effort on the part of Gautam Vasudev Menon in narrating a clean romantic story without any deviation from the plot" and further cited "As is Menon's forte, the dialogues and the execution of scenes are top-notch.
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