It's the Christmas season. Simon discovers that Rose (Sarah Thompson) may have secrets, and begins to wonder if his parents were correct when they warned him not to rush into marriage. Meanwhile, Kevin and Martin come to blows over Martin's attitude about becoming a father and Eric and Annie finally allow Ruthie to date Jack (guest star Garrett Strommen). Simon drops by to Glen Oak to talk to Eric and have...pie. Rose tells her dad about her being embarrassed about his numerous failed marriages as well as her mother's numerous relationships. That is the reason why she hasn't introduced her family to Simon yet. Philip encourages Rose to hold back on marriage with Simon and just live with him, while Rose debates that she tried that and the Camdens hate her even more.

As Rose gets ready to make a huge announcement, Simon breaks down as he realizes that he may have trapped himself in a marriage that he does not want. Meanwhile, Eric and Annie reminisce about their children and their younger days as they prepare for the rehearsal dinner and meet Rose's unconventional parents.

Simon and Rose prepare for their wedding day, despite speculation that it is not the right decision. Annie and Eric go through countless scenarios in their minds as they reflect on how the wedding will actually turn out.Meanwhile, Rose's former boyfriend shows up unexpectedly. Ruthie considers studying in Scotland over the summer. Kevin, Lucy, Matt, and Sarah all have life-changing news, if only they can find the perfect time to share it with the family...and the surprises don't stop there!