Jane (Katherine Heigl) has always been good at taking care of others, but not so much in looking after herself. Her entire life has been about making people happy -- and she has a closet full of 27 bridesmaid dresses to prove it. One memorable evening, Jane manages to shuttle between wedding receptions in Manhattan and Brooklyn, a feat witnessed by Kevin (James Marsden), a newspaper reporter who realizes that a story about this wedding junkie is his ticket off the newspaper's bridal beat.
Jane finds Kevin's cynicism counter to everything she holds dear -- namely weddings, and the two lock horns. Further complicating Jane's once perfectly-ordered life is the arrival of younger sister Tess (Malin Akerman). Tess immediately captures the heart of Jane's boss, George (Edward Burns). Tess enlists her always-accommodating sister to plan yet another wedding -- Tess and George's -- but Jane's feelings for him lead to shocking revelations... and maybe the beginning of a new life.