Jane, a romantic yet perpetually single woman, has made a hobby out of being a bridesmaid. With 27 bridesmaid dresses in her closet, Jane seems to live to serve the brides in her life, embodying the go-to gal for wedding planning and emergencies. Her own desires and dreams, particularly her long-standing crush on her boss, George, take a backseat to her role as the perfect bridesmaid. In contrast to her romantic fantasies, Jane's reality is filled with organizing bridal showers and managing wedding crises, all while keeping her own feelings for George a secret.

Jane's life takes a turn when her younger sister, Tess, arrives in town and quickly captures George's heart, leading to their swift engagement. Jane is forced into the role of the wedding planner for the sister she envies and the man she loves. Meanwhile, a cynical newspaper reporter, Kevin, becomes interested in Jane's story of perpetual bridesmaid, seeing it as his ticket to a more prestigious journalism assignment. As Kevin spends more time with Jane under the guise of writing a feature about her, their initial antagonism turns into something more complex. Amid planning her sister's wedding and dealing with her growing feelings for Kevin, Jane begins to reevaluate her role as the perpetual bridesmaid and starts to envision a different path for her life.