27 Dresses is a 2008 romantic comedy film directed by Anne Fletcher and written by Aline Brosh McKenna. The film stars Katherine Heigl as Jane and James Marsden as Kevin.
Jane Nichols (Katherine Heigl) has been a bridesmaid for twenty-seven weddings. One night when she is attending two weddings almost simultaneously, she meets Kevin Doyle (James Marsden), who helps her home but disgusts her with his cynical views of marriage and finds the planner she left behind in the taxi they shared.
Meanwhile, Jane’s sister Tess (Malin Akerman) falls in love with Jane’s boss George (Edward Burns). Tess pretends to like the same things George does so that she can get him to like her; despite loving George herself, Jane does not reveal the truth and the courtship progresses rapidly. Soon the new couple announce that they intend to marry in only three weeks. The reporter who agrees to cover their wedding for the society page turns out to be Kevin, who writes wedding announcements under a pseudonym. The reason he didn’t return Jane’s planner, after finding it, was so he could gather material for a piece on the “perennial bridesmaid” and hopefully be promoted to writing investigative pieces about “real” news.
Jane is unaware of Kevin’s intentions, and when he asks to interview her for his column on Tess, gets her to try on all 27 bridesmaids dresses in her closet. He takes pictures of her in all of them and sends the completed article to his boss. As they get to know each other because of Tess’s wedding, Kevin begins to think that Jane is not as one-dimensional as he thought, and asks his editor to hold his article so he can “fix” it.
Jane becomes increasingly uncomfortable with the fact that Tess still hasn’t been honest with George. She almost tells George the truth about her sister when Tess is away and Jane is the one helping him choose dinner for the reception. Kevin walks in on the meal and realizes that Jane is in love with George and can’t understand how she can go on planning her sister’s wedding. Kevin and Jane drive to Rhineback to pick up linens for the wedding, they get stuck in a rain storm and eventually so does their car. After they seek shelter at a bar, they get drunk and sing Bennie and the Jets. Then they have sex in the back of the car.
The next day, Kevin’s article is published along with all the pictures of Jane in her dresses, leaving her hurt and embarrassed. Upon getting back to the city, she must also deal with an enraged Tess whom Kevin had portrayed (somewhat correctly) as a bridezilla. To save her own face, Tess writes a script of what she wants Jane to say along with the slide-show to be shown at the rehearsal dinner. Jane says what Tess wants, but fills the slide-show with pictures depicting the real Tess and George finally learns that she isn’t who he thought. The wedding is called off and Jane sees Kevin as she leaves the dinner. He gives her a blackberry to replace her filofax, telling Jane that he was happy she finally stood up for herself and though she is mad at him about the article, he just wanted to come to the dinner and be there for her.
Later at work, George tells Jane that he appreciates her because she never says no. Remembering that Kevin once said the same thing as a criticism, Jane quits and admits she only stayed at the job because she was in love with George. She discovers after an experimental kiss that she no longer loves him and decides to meet Kevin. She announces in front of the entire crowd at a wedding that he is covering that she is in love with him.
One year later, Jane puts on her 28th dress – her wedding dress. George and Tess meet again since breaking up, and Tess reintroduces herself, being completely honest this time. All 27 brides Jane has been a bridesmaid for, as well as Tess and Casey (Judy Greer), Jane’s best friend, are her bridesmaids. The fact fulfills something Jane once said to Kevin, that she was willing to put on the silly dresses because one day it would be her turn and that all those women would be there for her, too.