The superhit 2009 film ‘Love Aaj Kal’, starring Saif Ali Khan, Deepika Padukone, and Rishi Kapoor in pivotal roles, has established itself as a classic rom-com for many Bollywood fans. The film, which reflected on the changing conceptions of love by featuring two separate love stories from different eras simultaneously, remains a point of pride for all involved. However, Imtiaz Ali’s third directorial venture faced casting challenges. Saif Ali Khan, who produced the film, wanted his then-girlfriend Kareena Kapoor to star in it, instead of Deepika, and even tried to convince Imtiaz to cast her.

On the other hand, Kareena Kapoor, who had achieved immense fame with Imtiaz Ali’s 2007 superhit ‘Jab We Met’, was eager to land a role in ‘Love Aaj Kal’, believing that her successful performance as Geet in the 2007 film would make her a natural choice. She was also convinced that she would be cast opposite Saif, given that her boyfriend was producing the film. However, Imtiaz Ali had envisioned Deepika Padukone for the role since her modeling days, even before her debut in ‘Om Shanti Om’. The issue became public when Kareena expressed her disappointment and anger about not being cast in the film during an award show.

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Kareena’s public outburst was not well-received by the filmmaker, who reflected on it in an interview with Indian Express. When asked if he felt flattered by Kareena’s determination to work with him, he replied, “The thing with flattery is that you don’t recognize it when it happens. It was not a happy feeling when Kareena publicly said what she did. I felt bad because we had resolved the issue, and I didn’t realize she still felt so strongly about it.”

When Filmfare asked Deepika Padukone to comment on desire of Kareena to star in the film, she said she was unaware of it and that she and Saif had never discussed it. All she knew was that the director wanted her for the role, and it happened. Deepika added, “I don’t expect that every film I do has to be with my boyfriend. I think that’s a bit ridiculous. As an actor, I’ll have to work with different kinds of people. A director knows the kind of characters he wants in his film and the actors who can play those characters. So, it would be a bit ridiculous to expect that my real-life boyfriend will be my co-star in every film of mine.” She also acknowledged Kareena’s perspective, given the success of ‘Jab We Met’.

Although Saif Ali Khan also wanted Kareena to take the role, he ultimately supported Imtiaz’s decision, believing that directors have a vision for their films and actors should respect their casting choices.