Madeline has always been extremely close to her family, so she is shocked when her older brother gets engaged without including them (or even giving them a heads up!). Mads has never been the biggest fan of his fiancée, Katie, so in order to remain one happy family, she is determined to bond with Katie before the big day, which includes reluctantly agreeing to be a bridesmaid. During a late-night bridesmaids-only game of "Truth or Dare" Mads is cornered into revealing she has never been kissed or even been on a date, which spurs the other girls to unite on a quest to find Mads the perfect plus-one for the wedding. Next thing she knows she's navigating a series of disastrous dates that include some major misunderstandings and mishaps. All of a sudden Mads finds her heart tugged in different directions: to Connor, the boy next door who knows her best. To Marco, the former classmate who knows how to push all her buttons. And to some of the new suitors who surprisingly aren't all bad. As the wedding draws nearer, Mads has to figure out who she wants most as a dance partner, while also making sure her brother isn't making the biggest mistake of his life.