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!
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.
The men have secrets they're trying to hide from the women in their lives: Kevin and Eric keep their wedding-ring troubles to themselves, and Simon leaves Rose in the dark about his schoolwork problem but all three guys come to realize the gals are not as clueless as they'd hoped. Brenda Camden and Nixon return to town with their one-year-old son Oliver, as the couple try to keep their news a secret but can't seem to that they are expecting their second child together, giving more happiness within the family. Eliza Jones returns to town finding out she's going to be a great-grandmother again bringing happiness to her. Brenda and Nixon take Oliver and return to New York after business gets in the way of family time together. Eliza heads back to Texas to celebrate the news there with her family.
The twins use an interesting weapon to coax the entire family into sharing their personal secrets. As everyone figures out what's going on, there are hurt feelings and confusion as they try to guess what's being hidden from them, and it turns out that Ruthie might have the biggest surprise of all. Meanwhile, the famiy doesn't quite understand Annie's newfound fondness for Rose, and it is especially irritating for Lucy and Ruthie.
The Camdens receive official invitations to Simon and Rose's wedding, and to their dismay, they learn that the date conflicts with Matt and Sarah's graduation from medical school. As this news creates a tailspin with the family, Rose stubbornly refuses to change the wedding date. Eric and Kevin think they have a solution to the problem, but when Annie disapproves of their methods, she looks for help from an entirely different source. Meanwhile, Ruthie wants to enroll in a summer program that takes place in Scotland.
Ruthie meets a troubled girl in detention, where a music teacher is assigned to watch the students. The girls bond over the lessons about Gershwin, as Ruthie tries to nurse her broken heart. She offers to help her new friend, who refuses any charity, but the Camdens become involved and refuse to take no for an answer.
As Sandy prepares to give birth, almost everyone rallies around her at the hospital. Everybody hopes that Martin--who has an important baseball tryout with a talent scout--will take what might be his very last chance to accept responsibility for his actions. Meanwhile, Kevin and Lucy are at odds over the idea of having more children, while Simon and Rose's relationship appears to be on its last straw--much to the Camden family's delight.
Racism comes to light at the high school when Alex, a new African-American student, wants to give a report on Dr. Martin Luther King, but his teacher argues that they have already covered that topic in class. When Martin inadvertently supports Alex's case, he falls victim to a hate crime. His car is defaced with racial slurs, and he refuses to wash it off until the culprit is caught. Meanwhile, for her own report, Ruthie attempts to recycle an essay that she wrote three years ago.
The Camdens are in the Christmas spirit in this episode. In a montage with the song ""Rocking Around the Christmas Tree"", Eric is spending time at a retirement home and dancing with the elderly patrons. Ruthie is volunteering at the hospital and gives gifts to kid patients, even her old friend Katelyn (guest star Katelyn Salmont). Lucy is working for Habitat for Humanity again. Annie, Sam, and David are talking and spending time to Sudanese students at a Catholic church. Kevin dresses up as Santa and hands out gifts at the pool hall with Savannah by his side. Kevin takes a lost dog to the kennel, but changes his mind afterwards and gives it to a deserving family.
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.
Eric meets Sandy's father, who gives him an envelope of money intended for Sandy; and Ruthie collects soup-can labels to help her school's newspaper. Elsewhere, Simon has money troubles and his phone service gets shut off; and Martin has a heart-to-heart talk with Meredith about their future. Sandy: Haylie Duff. Meredith: Megan Henning. Edward: Michael McDonald. Beau: Costas Mandylor.