Thirty-something Hillary Burns has spent her life trying to get the approval of her parents (most specifically her judgmental mother, Meredith Burns) thus far without success. Part of that approval for Hillary is to marry the right man. That's why Hillary is so happy she is engaged to successful lawyer Jason King, whom she will bring home to meet the family for the first time at their Thanksgiving get-together weekend in a week's time; however, Hillary's life starts to fall apart when simultaneously she loses her part-time newspaper writing job (when the newspaper itself folds) and Jason dumps her to focus on his career (which is seemingly more important to him than Hillary). On the advice of her best friend Sophie, Hillary - who feels she can't go home without Jason (especially as her two sisters' lives seem to meet their mother's approval) - decides reluctantly to go to an online dating site to find someone to pose as Jason for the upcoming family weekend. She finds David, an actor who seems to be struggling with his own life; but, as an actor, she figures he can at least treat it like a real acting job (which he hasn't had in a while). It may be a struggle for David to pretend to be Jason for four days, especially as Hillary's politician father, Roy Burns, always seems to be seeking legal advice. Those problems may be compounded by Hillary herself, who treats David like the real Jason in the hopes that all the wedding planning she goes through with Meredith will end up not going to waste in the possibility that Jason may come back to her. By the end of the weekend, Hillary may finally come to some realizations about her mother and her sisters (the latter whose lives aren't as perfect as on first glance) and what - and perhaps who - she herself really wants in life, especially as an unexpected person also shows up for the weekend.