Jane 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. He helps her to her taxi and brings her home. Jane accidentally leaves her planner in the cab, and Kevin picks it up. Kevin ends up being the person who writes the Commitments page for the New York Journal, Malcolm Doyle. However, he aspires to write larger articles, real articles. After seeing Jane's planner, he decides to write about 'the perpetual bridesmaid.' The next day, Kevin/Malcolm sends Jane flowers, however, she doesn't know it was him. Her friend from the office, Gina, then confirms Jane is attending her engagement party that evening. It is revealed she is in love with her boss, George. Apparently, 'everyone but George knows.' 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 was about to confess her love to him. Kevin showed up and Jane has her planner returned. Malcolm 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, and 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, although Jane was supposed to get it. Tess gets it altered significantly, takes Jane's ideal wedding plans. Jane finds out that Kevin is Malcolm Doyle, and Tess, not knowing about the previous weddings, tells Malcolm that Jane is his number one fan, and that she cuts out all his articles. Jane thinks Malcolm 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. Jane has to plan out Tess' wedding, and while scanning things for a bridal registry, she decides to say no, and she and Malcolm register Tess for the ugliest things. Jane and George meet to discuss the wedding food. Malcolm walks in, and realizes Jane is in love with George. He insists he take Jane to a family dinner with George and confronts her about it. Jane's car breaks down in a ditch during a storm. The two decide to find a phone in a bar, but there is none. Both end up getting drunk and dancing on the counter. Later, they have sex in Jane's car and go out to breakfast. There, Jane sees the article Malcolm wrote about her before he really knew her. She gets extremely angry. However, she does make a slideshow to show at Tess and George's engagement party. Tess had instructed her only to say certain things. But Jane showed pictures of Tess with other guys and eating ribs and holding a cat by the tail. George breaks off the engagement. In the end, Jane and George kiss, but there isn't any chemistry. The phone rings at that moment then Jane found out that she loves Kevin. She found Kevin in someone else's wedding and said she loves him in front of crowd. The story flashes forward to Malcolm and Jane's wedding one year later.