A single woman who has served as a bridesmaid a shocking 27 times wrestles with the prospect of supporting her sister at the altar on number 28, despite having fallen helplessly in love with her smitten sibling's handsome husband-to-be. Jane (Katherine Heigl) has the kind of altruistic traits that everyone looks for in a friend, yet lately the perennial bridesmaid has begun to feel as if something is missing in her life. One night, local newspaper reporter Kevin (James Marsden) spots the devoted bridal attendant racing between receptions in Manhattan and Brooklyn, and quickly surmises that her quirky tale may be just the story to get him off the bridal beat and into the big time. Immediately suspicious of the cynical reporter's motivations, Jane butts heads with Kevin just as her younger sister Tess (Malin Akerman) shows up in town. While Jane has always put the needs of friends and family before her own wants and desires, she's suddenly prompted to reevaluate her priorities when her boss -- with whom she is secretly in love -- falls for her younger sister Tess. When Tess and Jane's boss George (Edward Burns) make plans to marry, the smitten younger sibling mistakenly assumes that her lovelorn older sibling will be happy to take part in the wedding. For as far back as Jane can remember, she has sacrificed her own happiness for the sake of those she holds dearest, but now that her heart has been broken, she's finally found the courage to be honest with herself. Now, as Jane finally comes to terms with her true feelings, her life begins to change in ways she never expected. Judy Greer and Melora Hardin co-star in a romantic comedy scripted by The Devil Wears Prada screenwriter Aline Brosh McKenna and directed by Anne Fletcher (Step Up).