Aahana Swrup
‘27 Dresses,’ the 2008 rom-com starring Katherine Heigl as the protagonist, follows the story of Jane Nichols, a hopeless romantic who has attended numerous weddings as a bridesmaid but never one as a bride. However, fate plays a particularly cruel joke on her when she becomes the bridesmaid— and unwitting wedding planner— in her sister Tess’ wedding to George, Jane’s boss and the man of her dreams. As the preparations for the dreaded day commence, Jane must decide whether to put her needs before her sister’s— or subscribe to charming Kevin’s philosophy that love and marriage are nothing but a farce!
Jane’s character, defined by her caring personality, predictably falls in love with George, her boss, who is in constant need of her attention at work as his personal assistant. Meanwhile, Kevin, a new addition to Jane’s life, challenges her beliefs and keeps the woman on her toes. Thus, as the viewers accompany Jane in her story, their curiosity must remain piqued on where the narrative takes the woman’s love life. SPOILERS AHEAD!
Jane’s Perpetual Pining Over George
Through Jane’s introduction into the story as a reliable friend, high in demand for bridesmaid duties, the narrative establishes the character’s desire for a wedding of her own. Even though Jane adores helping her friends during their special days, she can’t help but wish the same for herself. Nevertheless, Jane is entirely single, with a wedding nowhere on the horizon for the woman.
Part of the reason stems from Jane’s feelings for her boss, George. Jane joined George’s entrepreneurial company as his personal assistant following her graduation from college. Soon, she fell head-over-heels in love with the man and never gave up the position to progress in her career. Thus, Jane remained stunted professionally as well as romantically— desperately pining after a man who never appreciated her as anything more than his assistant.
For the same reason, George’s meeting and instant attraction with Tess, Jane’s sister, strikes a chord with the latter. While Tess is charming and magnetic on her own, she purposefully lies about her interests and past to impress George. Consequently, with Tess becoming George’s ideal partner, the two quickly got engaged and began preparations for their wedding. Yet, Tess’ flaky personality and George’s disinterest in bearing the brunt of the wedding planning leave the responsibility on Jane, Tess’ maid of honor.
Jane— a textbook people pleaser— is unable to turn down the couple’s request, condemning herself to plan the wedding of the man she’s in love with to someone other than herself. Nevertheless, she remains quiet about her feelings and goes along with the tortuous development. Yet, eventually, after another personal crisis— involving a charming man named Kevin— Jane loses her cool and publicly reveals Tess’ lies, unable to let George marry someone who has been lying to him since day one.
The act effectively leads George to end his relationship with Tess and call off the wedding. However, shortly after Jane’s eternal crush becomes single again, the woman realizes that her relationship with George has always been incredibly one-sided. George has been a close friend for a long time, and he appreciates her efforts toward the job. Still, the fact remains that George’s affection toward her— platonic or potentially romantic— only emerges as a result of her resourcefulness to him. Inversely, Jane, who thrives on helping people— be it as a sibling, a bridesmaid, or a personal assistant— gravitates toward George because he has a constant need for her.
With this realization, it becomes easier for Jane to blurt out her feelings for George in her bewilderment. Yet, even though the confession leads to a few kisses, the pair easily realize that there’s no spark between them. George has only ever been a fantasy for Jane. Her feelings for him may have been true at one point. Nonetheless, for a long time now, she has only been holding on to him as an emotional crutch to stop herself from opening up to someone else.
Jane and Kevin: The 28th Wedding
Kevin’s arrival into Jane’s life remains unexpected, yet uniquely fateful, with their relationship progressing in a similar manner. Kevin is a writer who works in the “Commitments” section of the New York Journal, which pens articles about people’s weddings, providing readers with a short summation of their real-life relationships. Ironically, Kevin himself is a giant cynic when it comes to love and marriage— or at least, that’s the image he puts out into the world.
As such, once Kevin realizes that Jane has been a bridesmaid more than 20 times without a wedding of her own, he comes up with the idea for a piece about her experience to showcase the absurdity of the wedding culture. For the same reason, after their meet-cute (or meet-ugly, depending on one’s perspective) at a wedding, Kevin begins pursuing the woman. The relationship between the pair remains playfully antagonistic, with constant snipping and bickering.
Eventually, Tess’ engagement brings Kevin into Jane’s orbit after he approaches the younger Nichols sister under the guise of writing an article. Therefore, he discovers that Jane is actually a huge fan of his work, written under a pseudonym, treating them as reverent evidence of true love. In turn, the same revelation also informs Jane that Kevin pretends to be a pessimist about love because his wife left him for his college roommate in the past.
Over the course of their budding relationship, where they warm up to each other from enemies to tentative friends, Kevin begins to understand Jane in an honest and genuine manner. He recognizes that others have only ever wanted Jane to look after their needs. However, unlike others, Kevin wants to support Jane and look after her.
Their growing attraction inevitably leads to a fateful moment when their car gets stuck in a field, compelling them to seek shelter from the rain at a local dive bar. As such, the two end up sharing an enjoyable night of impromptu tipsy karaoke, leading to them sleeping together. Nevertheless, after Kevin’s article about Jane runs in the paper the next morning— without the writer’s knowledge— it drives a wedge between the pair.
Yet, the same incident also leads Jane to ruin Tess and George’s engagement— which helps her register the frailty of her feelings for the other man. As a result, Jane realizes that she actually wants to give Kevin a chance, leading to a chase through the docks that ends in a confession aboard a wedding yacht on the sea. In the end, Jess ends up with Kevin, with the two sharing their first kiss at a stranger’s wedding. A year later, the couple went on to marry each other.
Read More: 27 Dresses: Is There a Real-Life Inspiration Behind the Film?
