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In 2009, Kapoor was cast as Simrita Rai opposite Akshay Kumar in Sabbir Khan's battle of the sexes comedy Kambakkht Ishq. Set in Los Angeles, California, it became the first Indian film in history to be shot within Universal Studios Hollywood, California, and featured several cameo appearances from Hollywood actors.The film earned over Indian Rupee 840 , but was a critical failureThe Times of India described her performance as "a complete let-down" and further stated that "despite her haute-coutured look, her micro minis, her pencil heels, she comes across as a completely unconvincing supermodel cum surgeon She next starred in Prem Soni's directorial debut, Main Aurr Mrs Khanna. Kapoor featured as the protagonist, Raina Khanna, a woman who becomes the sole breadwinner of the family, and therefore strules with her marriage. The film was critically and financially unsuccessfulwith the Daily News and Analysis concluding that "Kapoor shows moments of the talent we associate with her, but then slumps with a silly drunken scene or by just smiling beatifically through emotional moments.

Kapoor returned to film as the female protagonist Geet Dhillon, a vivacious Sikh girl with a strong zest for life, in the Imtiaz Ali directed romantic comedy Jab We Met (2007). Featured opposite Shahid Kapoor, the film relates the story of two people with contrasting personalities who meet on a train and eventually fall in love. The film was received favourably by critics and became one of the year's most successful films, with a domestic box office of Indian Rupee 303 won several awards for her performance, including the Filmfare Award for Best Actress and her second Star Screen Award for Best Actress.Rajeev Masand from CNN-IBN noted, "Uninhibited and spontaneous, Kareena Kapoor is the soul of this picture, its , as she brings alive her character with not just those smart lines, but with the kind of candor actors seldom invest in their work While shooting for Jab We Met, Kapoor and Shahid ended their three-year relationshipAsked in Mumbai Mirror about their well-publicized break-up, she stated that "I hold him in utmost regard, and I hope one day we could be good friends. He is a great guyDuring this period, speculation began to surface that she was dating actor Saif Ali Khan, her co-star in the film Tashan (2008) On October 18, 2007, during Manish Malhotra's grand finale show at the Lakme Fashion Week, Khan confirmed their relationship to the media
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor
Kareena Kapoor