Always Kabhi Kabhi focuses on four students and their struggle through their final year at St Mark's School. The first teenager is 'Shortcut Sam', Sameer Khanna,, the jock, who falls in love with Aishwarya Dhawan who is about to become a Bollywood actress. Aishwarya is a new student who befriends Sam on her first day, and the two fall in love at first sight. A Shakespeare play approaches in which Aish automatically gains the role of Juliet, much to the chagrin of her classmates. Sam tries his level best to learn the lines of Romeo so as to impress Mrs. Das and gain the role of Romeo. He succeeds in the end. The next two friends, Tariq Naqvi and 'Nandy Bull', Nandini Oberoi, love to fight and argue with each other, but do not understand that they are in love. Nandini's parents don't spend any time with her and are always travelling. In the absence of her parents, she goes to illegal clubs and parties every day and spends money lavishly. Tariq, on the other hand, is burdened by his parents to achieve their dream of studying in MIT. They realise their love for each other during Nandy's struggle to get approval of her apology after she forwards Tariq's MIT denial letter, oblivious that he had not read it himself. Sam gives a party in Hellfire but then there's a raid and he gets arrested while saving Aish. The two corrupt policemen try to bag from Sam. He tries his best to avoid the policemen and tries to pay them in instalments. Aish breaks up with him because when during the party, Nandy's toyboy offers him a drag, even though Aish begged him to leave, he agreed to smoke weed because the toyboy makes fun of him and asked him to be a man. After she heard that Sam had sacrificed himself to save her, they make up. During Aish's 18th birthday, Sam confesses his love for her only to be caught together by her mother, who disapproves of them. Her agent renames her Kashish for the films and even persuades her to do a photo shoot in which she only has to wear a bikini. When Sam finds out that the prize money of the inter-school Shakespeare play competition is , he begins to put more pressure on the group to come in time for the practices. Meanwhile, Aish is being offered a movie contract that she doesn't want to do. During a meeting, she rips the contract and runs to meet Sam and the others and continue their practice for the competition. Enraged by Aish's absence during practice, Sam confronts her, oblivious to what she had done for him. Aish didn't know about the money he owes the policemen and does not understand the reason of his anger. She runs into the streets, distraught and crying, only to be hit by a car and go into coma. Aishwarya's mother confronts Sam about the accident because she believed that he was the cause and does not permit him to see her. While dropping Aishwarya's clothes, Tariq and Nandy notice Aishwarya's phone has an electronic diary and reads it. It shows her point of view about everyone in the group and talks about how their parents have pressurised them. So, they perform Romeo and Juliet with a different point of view, saying that Romeo and Juliet would not have died if their parents had approved of their love and listened to them, implying that their parents should do the same. They perform the song "Antenna" to convey their thoughts. Sameer uncovers the policemen's intentions to the Commissioner, while Aishwarya recovers and reconciles with him. Tariq gets into IIT and tries to make his father consider it the same as MIT and Nandini tells her parents she does not want their money, but their time. The movie closes with Shahrukh Khan performing to a song with the protagonists.
Always Kabhi Kabhi opened to negative reviews from critics. Taran Adarsh of Bollywood Hungama rated the film with one and a half stars out of five saying, "Always Kabhi Kabhi disappoints!". Rajeev Masand of CNN-IBN also gave the film 1.5 stars and stated, "Watching this film is like attending a concert put up by ten-year-olds. It's amateurish, and tedious to sit through, and the only thing you can appreciate in the end is the earnestness behind the effort." Nikhat Kazmi of the Times of India awarded two and a half stars saying, "First, and most importantly, the film is a youth-oriented story but completely lacks the fun and games that are associated with this generation. Secondly, the parental problems are all so very predictable. It's all foregone and predictable apart from being inordinately long. School is agony; school is ecstasy. Always Kabhi Kabhi captures neither and treads the staid middle ground."
Box office
Always Kabhi Kabhi had a net gross of in India by the end of theatrical run. It was declared a flop by Box Office India In the overseas, the film grossed $21,381 from the United States, $46,469 from the UK, $9,803 from South Africa and $2,893 from Malaysia.