In the Gossip Girl series of books, Dan and Serena date very briefly but break Tumblr llrray1qij As a result, they have sex for the first time in Victor Victrola. . Girl on Blair and Chuck's car accident (Riding in Town Cars With Boys ). Endless Love - Jade's First Time: Jade (Gabriella Wilde) loses her virginity to David (Alex Pettyfer). BUY THE MOVIE.