Kassandra is a single, independent woman who prides herself on her own success. But when she’s asked by her best friend Laura to be the Maid of Honor in her wedding, Kassandra finds herself questioning her lifestyle. Helping Laura plan the wedding is no problem—she’s done it before for all their other friends. The first time was a blast, the second super fun, but doing it without receiving any help from the rest of the girls gets old really fast.
The whole event kicks off with the worst kind of surprise when Kassandra discovers who her friend's fiancé really is, and she's torn between supporting Laura's future happiness and hiding the deeply buried, intimate past she shares with the groom-to-be. Struggling to be the bigger person and do all the hard work on her own, Kassandra finds surprising comfort in Josh, the best man in the wedding and someone she's been avoiding for years. He's charming, thoughtful, handsome, and the worst kind of womanizer, but she just can't seem to stay away. All the while, Kassandra can't help wondering if the wedding could be any more cliché—until she finds unexpected ways to change things up a bit.