Penty began her modeling work when she sent her photographs to Elite Models India, who liked her work and suggested she take on modeling tasks. At this point she was in college and was reluctant to choose a career in modeling, so Penty decided to work part time as a model. In 2005, Penty officially began working for Elite Models India and debuted at the Indo-Italian Festival for Italian designers Nicola Trussardi and Gianfranco Ferré. Subsequently, Penty was inspired by several other Indian designers, including Wendell Rodricks, Rohit Bal and Rina Dhaka. In 2007, she had achieved a modeling career after participating in print campaigns for some of India's most prominent brands, including Tribhovandas Bhimji Zaveri, Parachute and Westside; as well as on the covers of some Indian fashion magazines.
Penty was originally scheduled to debut at Bollywood in 2011 with Imtiaz Ali's Rockstar facing Ranbir Kapoor, although she rejected the film due to her modeling engagements at the time and was later replaced by Nargis Fakhri . She then entered the Homi Adajania cocktail instead; at Ali's suggestion. Alongside Saif Ali Khan and Deepika Padukone, the film received mixed reviews. Meera's portrayal of Penty, a simple Indian with traditional values, has been well received by critics. Taran Adarsh, of Bollywood Hungama, commented that "Diana, who debuted as an actress, portrays a rather difficult character for her first film, has a very disarming innocence in her role and she impresses a lot." Raja Sen agreed, mentioning that she is "naturally refreshing". Anupama Chopra added that "Diana struggles with the most colorless character but infuses her role with calm calmness and maintains herself."
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