Jane Nichols (Katherine Heigl) has been a bridesmaid for twenty-seven weddings. One night when she is attending two weddings almost simultaneously, she is trampled by a crowd trying to catch the bride's bouquet. A man helps her up and introduces himself as Kevin Doyle (James Marsden). He helps her to her taxi and brings her home. He is on his way home when he realizes Jane accidentally left her planner in the cab, and Kevin picks it up. It turns out that Kevin is the person who writes the Commitments page for the New York City Journal, under the pseudonym of Malcolm Doyle, who happens to be Jane's favorite writer. However, he aspires to write larger articles, real articles. After seeing Jane's planner, he decides to write about "the perpetual bridesmaid" so he can move up farther in his career. He just plans to use Jane, who is unaware that Kevin is Malcolm Doyle, for his own means.
The next day, Kevin sends Jane flowers, but she does not know he was the one who sent them. Her friend from the office, Gina, confirms that Jane is attending her engagement party that evening. It is revealed Jane is in love with her boss, George, who is the only one who doesn't know about Jane's feelings for him. Jane's younger sister, Tess, comes to visit and decides to come to the party. At the party, George asks if what he left on Jane's desk was all right with her, if their new type of relationship was all right. Jane is convinced by her friend Casey that he was the one who sent her the flowers. Jane later learns he had left a dry cleaning slip on her desk, right before she is about to confess her love to him. Kevin appears and Jane has her planner returned. He has torn out a week and written his name and phone number on every Saturday for the rest of the year.
Tess and George meet, and then go dancing. Tess comes home in the morning, and it is evident that she and George are together. Soon, Tess and George are dating and Tess finds out from Jane that George is a vegetarian, likes animals and the outdoors. Although Tess isn't any of these things, she pretends to be to get George to like her. Tess and George get engaged, and Jane's father gives Tess their mother's wedding dress, even though Jane was supposed to get it. Tess gets it altered significantly and takes Jane's ideal wedding plans.
Jane discovers that Kevin is Malcolm Doyle, and Tess, not knowing about the previous weddings, tells Kevin that Jane is his number one fan and that she cuts out all his articles. Jane thinks Kevin is a cynic and hates weddings, and when she finds out what he writes, she is shocked by his seemingly affectionate and beautiful articles. However, she still hates him. She discovers that the reasons he hates weddings is because his bride ran off with his roommate.
Kevin has Jane try on all her bridesmaid dresses and sends the article to his boss. She agrees to put it on the front page, but Kevin asks her to give him another week. He thinks he made Jane too one-dimensional, and is starting to fall for her.
Meanwhile, Jane has to plan out Tess' wedding, and while scanning things for a bridal registry, she and Kevin register Tess for the ugliest things. Jane and George meet to discuss the wedding food. Kevin walks in, and realizes Jane is in love with George. He insists he take George's place linen shopping, so that the groom-to-be can make a family dinner on time. While in the car with Jane, Kevin confronts her about her love for George. Jane denies it, and speeds up the road, causing the car to hydroplane, and become stuck in the mud at the side of the road. The two hike to a bar in the rain to find a phone, and as there is none, they have several drinks instead.
Kevin and Jane begin to talk and realize they both have something in common, their favorite part of weddings. They both like to look at the groom when the bride makes her grand entrance, so that they can see the expression on his face. Both end up getting drunk and dancing on the counter singing Bennie and the Jets. After they jump down, Kevin admits to Jane that he cries at some weddings, and they kiss. Later, they have sex in Jane's car and go out to breakfast. There, Jane sees the article Kevin wrote about her because his boss decided to just publish it as it was. She becomes extremely angry, and storms out. Kevin gets upset, not enjoying his new position. He realizes that unlike what his boss said, he didn't get everything he wanted. Tess gets extremely angry at the way Kevin portrayed her as Bridezilla, but decides to forgive Jane. After seeing that Tess has destroyed their mother's wedding dress in her alterations, Jane blows up and says if Tess doesn't tell George the truth about who she is, Jane will.
Tess however does nothing to the threat, So Jane makes a slideshow to show at Tess and George's engagement party. Tess had instructed her only to say certain things, but Jane shows pictures of Tess with other guys, eating ribs, and holding a cat by the tail. George breaks off the engagement, which upsets Tess, who is now angry at Jane. Kevin comes later that night and tells her how proud he is. He gives her a Palm Centro to keep track of her wedding stuff for all the trouble he caused her, and tells her he'll disappear from her life now. Tess and Jane eventually reconcile, and realize each other don't have it easy as the other thought.
In the end, George tells Jane he loves her because she never says no. Jane snaps out of her sadness and quits her job, admitting that she was in love with him. Jane and George kiss, but realize there isn't any chemistry. The phone rings at that moment to the song Kevin sung with her in the bar, and Jane realizes that she loves Kevin. She runs to find Kevin at someone else's wedding, where the bride recognizes her from Kevin's article and prompts Jane to say that she loves him in front of the wedding crowd. He admits to feeling the same way and the two kiss.
The story flashes forward to Kevin's and Jane's wedding one year later. Tess and George start all over, with Tess telling the truth this time. Jane wears her 28th dress and admits that though Kevin wasn't what she was looking for, he looked at her the way she always wanted to be looked at as she walks down the aisle. She also makes the 27 brides she was bridesmaid for wear the dresses she had to wear for each of their weddings. |
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