Jane, a romantic, completely selfless woman who has been a bridesmaid in no less than 27 weddings decides to change her "always-a-bridesmaid" destiny when her sister Tess captures the heart of Jane's boss (and secret crush).

High-powered book editor Maggie is everyone's worst nightmare: ruthless, driven, and tactless. When she finds herself faced with deportation back to Canada, she coerces her much younger assistant into marrying her. However, when the government becomes suspicious, they embark upon a charade in order to make the marriage seem legitimate.