Jane is career-oriented and secretly in love with her employer, George. She spends much of her time as a bridesmaid, and has 27 dresses as evidence. Then her structured and ordered life comes unhinged when her younger sister, Tess, re-enters her life, and a reporter, Kevin, is attracted to her. Kevin decides to publish Jane's secret and her overwhelming wardrobe. Things get even more complicated when Jane finds out she may end up losing George to none other than her very own sister.
Two things about Jane: she never says no to her friends (she's been a bridesmaid 27 times and selflessly plans friends' weddings), and she's in love with her boss, George, nurturing dreams of a lovely, romantic wedding of her own. She meets Kevin, a cynical writer who finds her attractive, and that same week her flirtatious younger sister Tess comes to town. Jane silently watches George fall for Tess, a manipulative pretender. Worse, Jane may be called upon to plan their wedding. Meanwhile, Kevin tries to get Jane's attention and has an idea that may advance his career. Can Jane uncork her feelings?