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Olivia is the daughter of real estate developer, of Italian descent, Douglas Palermo and interior designer Lynn Hutchings. Palermo grew up between the Upper East Side, New York and Greenwich, Connecticut where she attended Nightingale-Bamford School, and then St. Luke's School, where she was on the field hockey team. She attended the American University of Paris for a year and studied media at The New School in New York. Palermo's father filed for bankruptcy in 2007 after failing to pay $2.75 million to a creditor. However, it was overturned when the judge discovered he had used multiple fake organizations to obscure his actual worth to borrow money and join private clubs and send his children to expensive schools. She interned at Quest. Photographer Patrick McMullan spotted her at an auction, then took pictures of her about town. Palermo began taking part in the charity event circuit in New York, becoming a member of the Friends Committee of New Yorkers For Children and joining the committee of Operation Smile. Palermo found herself at the center of a controversy when she was reported to have sent out a letter to fellow socialites pleading for acceptance. This letter was forwarded to the owners of the social website, Socialite Rank.com who promptly published it. Palermo immediately denied the authenticity of the letter and filed a lawsuit against the website. The website was eventually shut down and in May 2007, Palermo appeared on the cover of New York Magazine in a story about the incident. Palermo has been dating model Johannes Huebl since 2008.