Avinash (Avi) (Rajkummar Rao) is visiting his relatives Kannu bua (Kiran Juneja) in Shimla. Naina (Rakul Preet Singh) runs a cafe in Shimla and has friend Brownie (Zoya Khan) & Captain Uncle (Shakti Kapoor), who runs the cafe day to day. Avi's mom (Nita Mohindra) is on the lookout for a suitable match for Avi and sees Naina one day and wonders if this beautiful girl could become her bahu. Avi sees Naina one day and falls head over heels in love with her. He gets a job as a odds job man in her cafe.
Rukmini (Hema Malini) is Naina's mom and still pines for Tilak (Kanwaljit Singh), who was her husband till he abandoned her for a younger girl, with whom he has a live in relationship now. Naina vows to get Rukmini married to another guy to break social conventions that men can marry again, but women can't. Meanwhile Avi tries to impress Naina by fixing her old decor cafe. Naina befriends Avi and they start spending some time together. Avi struggles to express his love to Naina verbally, so his friend Jude (Tarun Wadhwa) advises him to express his feelings via a letter. Avi writes Naina a love letter, but doesn't sign his name. Naina throws the anonymous letter away. But then Naina gets a brainwave and starts writing love letters to her own mom Rukmini (under an anonymous name), so that Rukmini moves on from Tilak in her life.
RUkmini is ecstatic that a stranger has fallen in love with her. She signs the divorce papers with Tilak and resumes her training of dance. Meanwhile Avi is not happy to find his letter to Naina in Rukmini's hands. Rukmini waits for the next letter, so to keep her mum's wishes, Naina writes her a letter and asks Avi to deliver it to their home. Rukmini is glad to see Avi delivering the letter and assumes that Avi is the one writing love letters to her. Rukmini confides in Naina, who knows that Avi has no feelings for Rukmini. to handle the situation without hurting her own mom, Naina begs Avi to pretend to love her mom for a few weeks.
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