Prince Harry has had numerous romantic connections over the years. The article lists his top 10 romantic interests which include Chelsy Davy, his longest relationship from 2004-2009, Florence Brudenell-Bruce in 2011, Pippa Middleton after her brother William's wedding in rumors, Caroline Flack in 2009 after Chelsy, and Astrid Harbord shortly after Chelsy in 2009. His other connections mentioned are Camilla Romestrand in 2010, Natalie Pinkham who denied a relationship, Paris Hilton in 2009 after Chelsy, Catherine Ommanney in 2010 who said they had a brief romance, and Natalie Imbruglia in 2009 who said they barely knew each other.