We first meet Jane (Katherine Heigl) on a evening in which she is juggling the role of bridesmaid at two weddings. She meets Khaleel (Michael Ziegfeld) her cab driver, who is very interested in watching her change as she moves from event to event. In this way we learn that she is just being Jane who has been a beautiful bridesmaid in many hideous dresses all which began when she was an 8 year-old who learned that she is skilled at helping with weddings and has difficulty refusing to help potential brides.
Her stash of dresses are packed in a hall closet that reminds us of an old radio show which contained Fibber McGee's closet. She keeps all the useless dresses somewhat for nostalgia and with the hope that she will eventually find someone to marry her. That someone in her mind is her boss (Edward Burns) who counts on her every day but has no romantic interest. Her best friend Casey (played with her usual comic twist by Judy Greer) advises her to tell her boss of her feelings or get a life. To make matters worst Jane's younger sister, played with arrogance and oblivion to others by Malin Akerman, looks stunning to her boss when she appears in a very fitted yellow dress. She may be shallow but he is fascinated.
Along comes reporter Kevin (James Marsden) who is witting a story about girls like Jane, "always a bridesmaid never a bride." It's obvious to all of us that he's the guy for her, but neither of them respond well to each other at the beginning.
While sister Tess plots to catch Burns' character the way Maggie McNamara did to Louis Jourdan in the old classic Three Coins in the Fountain, Jane is exposed in an embarrassing story on the front page of the Sunday supplement by Kevin.
The ending is as we would expect, and the 27 Dresses get used again, but the characters are paper thin and it becomes more and more difficult to expect audiences to see Katherine Heigl as the older sister who is admired for her organization skill rather than her stunning beauty. Her sister is attractive but pails in comparison. Why Heigl is cast as she is here and was in Knocked Up where she is paired with a fat dumb slob makes little sense. Heigl deserves better and so do we.