27 Dresses (2008) The film follows Jane Nichols (played by Katherine Heigl), a young woman who has been a bridesmaid 27 times but has never been a bride herself. Jane is selfless and always putting others first, especially when it comes to weddings, organizing every detail flawlessly. Secretly, she’s in love with her boss, George, but her world crumbles when her younger sister, Tess, gets engaged to him. As Jane struggles with her feelings, she crosses paths with cynical wedding journalist Kevin