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.