In 2006, she appeared in the film The Bong Connection (co-starring Shayan Munshi). Since then she has had two more hits with the action thriller Dus and the Bengali film Antar Mahal (where she had a very small role). After a few more average movies she had a critically acclaimed hit in 2005 with Parineeta, where she played the playmate of the film's heroine, played by the debutante Vidya Balan. Her breakthrough role came when she starred in the Rituparno Ghosh's film Chokher Bali.
She then starred in the film Daman playing Raveena Tandon's daughter, where her small performance was appreciated. Sen made her debut in the film Godmother, which was a critically acclaimed success, but her minor role may have been overlooked in favour of the protagonist, played by Shabana Azmi. Raima Sen in 2006 admitted that she had a brief relation with Odisha politician Kalikesh Narayan Singh Deo in 2006–2007, but the relationship did not last long. In an interview, she says while she enjoys Mumbai's faster pace of life, its gyms and its nightclubs, she misses her family in Kolkata, her dog Cuddles, and Kolkata's street food, notably Jhal Muri and Aloo chaat. Sen is said to resemble her grandmother much more than either her mother or her sister. The sisters are credited on-screen under their mother's maiden name, although their official papers carry the surname Dev Varma. Raima's maternal great-grandfather Adinath Sen was a prominent Kolkata businessman, whose son Dinanath Sen – a relative of former Union Law Minister Ashoke Kumar Sen- was the Diwan or a Minister of the Maharaja of Tripura. Her paternal great-grandmother Indira was the only daughter of Maharaja Sayajirao Gaekwad III of Baroda. Her paternal grandmother, Ila Devi, was the princess of Cooch Behar, whose younger sister Gayatri Devi was the Maharani of Jaipur. Their father Bharat Dev Varma is a member of the royal family of Tripura. Her sister Riya Sen is also in the Bollywood industry. Raima Sen was born on 7 November 1979 in Bombay (present-day Mumbai) to Moon Moon Sen and Bharat Dev Barma and the granddaughter of actress Suchitra Sen who is regarded as the Mahanayika of Bengali Cinema.
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