Please note that there will be spoilers, although none of them should come as a surprise if you've ever seen five minutes of a romantic comedy.
Katherine Heigl plays Jane, a perpetual bridesmaid and the owner of the 27 title dresses. Jane is super-organized, super-efficient, and super-super. She's super in love with weddings and romance and articles written by Malcolm Doyle, a wedding columnist for the New York Journal. She's also super in love with her boss George (note to self: blog about how George is not a sexy name), played by Edward Burns.
As mentioned earlier, K and I missed the 25th and 26th dresses because we missed the first ten minutes of the movie, but while wearing them, Jane meets Kevin Doyle (played by surprisingly adorable and just possibly outdoor material James Marsden). The next day, Jane arrives to work to find flowers on her desk and her sister Tess arrives from Italy and her super-glamourous life as. . . something. Missed that.
We can speed up this next part: Jane goes to party, George goes to party, George mentions he left something on Jane's desk, Jane assumes flowers, George means dry cleaning ticket, Tess shows up for drinks, George meets Tess. Oh, and Kevin sent the flowers.
Tess falls for George, George falls for Tess, and suddenly Jane is planning her sister's wedding to the man of Jane's dreams. In the meantime, Kevin is booking it after Jane--literally. In one of my favorite moments of the movie, Kevin returns Jane's day planner, but only after penning his name in every Saturday for the rest of the year.Here's the spoiler/twist you may not see coming: Kevin Doyle is Malcolm Doyle. He's writing an article about Tess and George--but he's also writing an article about Jane's state as a perpetual bridesmaid. Hence the booking. Sad, because he really is cute. Cynical and cute make an excellent leading man.
The movie works itself out exactly as it's supposed to, complete with a boat scene and "Benny and the Jets." And most importantly, as K pointed out, Jane gets around to kissing both guys. We awarded the movie 3.5 out of 5 stars, mostly because Marsden wasn't on screen enough. He really was that cute.