Katherine Heigl (Bride of Chucky)
James Marsden (Superman Returns)
Judy Greer (Two and A Half Men)
Krysten Ritter (Jessica Jones)
Melora Hardin (The Hot Chick)
Edward Burns (One Missed Call)
Malin Akerman (Watchmen)
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. He finds her day planner which she’d forgotten in the cab they shared. Meanwhile, Jane’s sister Tess (Malin Åkerman) falls in love with Jane’s boss George (Edward Burns) at first sight. Tess pretends to like the same things that George does so that she can get him to like her. Despite loving George herself, Jane does not reveal the truth and her sister’s courtship progresses rapidly. Soon the new couple announces that they intend to marry in only three weeks and Jane becomes the wedding planner.
The reporter who agrees to cover their wedding for the society page turns out to be Kevin, who writes wedding announcements under pseudonym Malcolm Doyle. Having looked at the contents of Jane’s planner before returning it, he then decides to use the contents as 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, he gets her to try on all 27 bridesmaids dresses in her closet. He takes pictures of her in all of them and sends them with 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.
When Kevin finds out that Jane is getting her sister’s marriage fixed with the man she loves, he rebukes her. Jane agrees to one drink with Kevin and ends up getting drunk. Kevin and Jane kiss and have sex in the car. Kevin’s editor runs the article anyway on the front page of the ‘Commitments’ section. When Jane finds out about it the next morning, she feels betrayed and is furious at him. Tess then gets angry at Jane for giving Kevin material about her, whom he describes as a bridezilla. The fight escalates when Jane realizes that Tess altered their late mother’s wedding dress to her own choice, the last straw on Tess’ string of lies to George and demands on Jane. Despite the fight, Tess still asks Jane to make a slideshow to show at her engagement party. Jane decides that George should know the truth about Tess and instead runs pictures of Tess with other men during her past years, eating ribs, and holding a cat by the tail – in short, doing all the things she had told George that she never did. After Pedro, the young Hispanic child that George mentors, tells the crowd that Tess had him cleaning George’s apartment for money, George breaks off the engagement.
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 he is covering that she is in love with him. One year later Jane and Kevin are now getting married. George and Tess meet in their wedding again, and a hope for a second chance shows. All 27 brides Jane helped, as well as Tess and Casey (Judy Greer), her best friend, are her bridesmaids, and they are wearing the dresses she once wore as their bridesmaid.