Matt is determined to settle down before heading off to medical school. While in search of a woman to marry, he goes out on a date Sarah, who is the daughter of a rabbi. Ruthie tries to set her brother straight by telling him not to do anything stupid. Eventually concern grows to fear for both families as both Matt and Sarah do not come home after their second date together in less than 24 hours.

Matt stays out all night with Sarah and they secretly elope, but when facing their parents they're only able to summon the courage to say that they're engaged. A worried Annie tries to calm Eric down, who is convinced that Matt did something foolish. Meanwhile, Lucy and Mary search for Ruthie because they suspect that she knows what really happened during Matt's night out. Ruthie and Matt agree to keep the marriage a secret until a Jewish wedding in a few months.

Annie frantically cooks Jewish dishes as the Camdens prepare to head out to a Shabbat dinner at the Glasses. Simon asks Matt and Sarah if he can bring his friend Morris to the dinner. Matt agrees to allow Morris to come to the dinner as he is half Jewish. Although, that does not go as he planned as he is not very knowledgeable about his faith. Lucy and Mary play sick to try to skip the outing so they can stay home with Robbie. While home, Mary flirts with Robbie. Lastly, Eric and Annie are unable to handle everything when they are shocked to find out during dinner that Matt is considering to convert to Judaism.

Matt and Sarah argue over their wedding plans and their agreement to forego buying an engagement ring and seek Eric for advice, who isn't happy with Matt for getting engaged in the first place. Because of Eric, Matt buys Sarah a fake engagement ring. Mary and Lucy fly to Buffalo for a weekend, or at least that's what Lucy thinks as Mary makes plans of her own. At the airport, Lucy meets a police officer who invites her and Mary to double-date with him and his brother.

A startled Eric catches Mary and Lucy in the kitchen with Ben and Kevin in the middle of the night. The guys end up spending the night in the living room with Mary ad Lucy. Ben and Kevin's sister calls the house to inform Ben and Kevin that their mom is going out with a neighbor. Eric suspects that Ruthie knows a secret about Matt and Sarah and thinks they are married already. Meanwhile, an older couple seeks guidance from Eric when they can't seem to let go of their forty-four-year-old son, who has run away from home.

The Colonel drops by to tell Ruthie about the death of a soldier she has been corresponding with. Ruthie shares her letters with the family. At the memorial service, Eric asks everyone to advocate good deeds and go out into the community, as the family does.

Matt and Eric meet with Rabbi Glass to discuss wedding plans, and Eric learns that he is playing a smaller role than he had originally planned. Annie prepared for fewer guests to attend the rehearsal dinner and gets very flustered when she does not have kosher food. Ginger and Charles are prepared to fly to Glenoak, but Charles get's lost at the airport. Simon gets angry when Matt asks Robbie to be his best man. Meanwhile, Ruthie tells Robbie that she wants his room for herself after Matt moves out. Ben proposes to Mary, but he gets an unexpected answer.

Matt and Sarah grieve over Eric's decision not to attend the nuptials following his argument with Rabbi Glass over Matt's conversion to Judaism. Hoping to patch things up between their fathers, Matt and Sarah seek their mothers' help in persuading them to put aside their differences before it's too late. Ben and Kevin come to Glenoak to meet up with Mary and Lucy so that they can resolve their problems. Robbie tries to figure out why Ruthie wants him to move out of the Camden household.

The extended Camden clan wrestles with their emotions as they await the outcome of Eric's double bypass surgery. While under anesthesia, Eric hallucinates that he's Elvis. Lucy finally realizes that Kevin is the one and that she's ready to marry him, but he refuses to propose until Eric gives them his blessing. Simon complains to Annie about the absence of Matt and Mary during their father's health crisis. Sarah also comes to Glen Oak to wish Eric well.

Eric flies to New York in a last attempt to convince Chandler's dying father to make peace with Chandler before it's too late. Meanwhile, Matt and Sarah suspect that she might be pregnant and Matt's co-worker lets the news slip to Eric; Lucy fears she might also be pregnant, which causes her to panic and push Kevin away; Mary tries to find Eric to tell him that she did something stupid; Lucy offers her classmate Christine a temporary place to live, unaware that she's hiding a big secret; Simon is crushed when Cecilia refuses to go to the prom with him; and no one can understand why Ruthie is acting especially strange.

Matt and Sarah begin their student rotation in the ER, but get off to a bad start by arriving late and angering Dr. Norton, the attending ER physician. Matt and Sarah's relationship is tested when Matt quickly demonstrates an aptitude for the work, but Sarah accuses him of trying to make himself look better than the other students, especially her. However, Matt ends up looking foolish when he can't figure out how to turn off the ringer on his cell phone and he gets stuck fielding calls from his family. Matt's day ends tragically, leaving him to question his destiny.

It's Camden chaos all around when Matt, who is having problems in his marriage to Sarah, returns to Glenoak for a visit and runs into his ex-girlfriend Heather on his flight to Glenoak. Simon unexpectedly announces he's coming home for the summer.

Also, Lucy sets out to discover why Roxanne is suddenly too busy to hang out with her as she's convinced that Roxanne is secretly trying to become a detective behind Kevin's back. Ruthie keeps a secret about a fellow student from her parents. Lastly, Martin learns that his baseball teammates think he's having sex with Cecilia.

The Camden chaos continues with Matt, who is trying to salvage his marriage, questioning whether he still has feelings for his ex-girlfriend Heather; Simon's return to Glenoak creates conflicted feelings for his ex-girlfriend Cecilia, who is torn between her feelings for Simon and her current boyfriend Martin; Ruthie's foreign exchange student friend Maria, appears to be making the moves on Ruthie's boyfriend Peter; and grandparents-to-be Eric and Annie hop a plane for New York, despite Mary's repeated pleas for her family to stay away.

With Thanksgiving just two weeks away, Eric and the kids notice that Annie is acting strangely, especially after she learns that Matt and Sarah (guest-star Sarah Danielle Madison) won't be able to spend the holidays in Glenoak. In fact, the majority of the family has made plans of their own and Eric worries how Annie will take the news. Mary (Jessica Biel does not appear in this episode) and Carlos (guest-star Carlos Ponce) decide to spend the holiday in Puerto Rico with Carlos' family and invite Ruthie to join them.

Meanwhile, Simon, who has something to tell his parents, but can't get up the nerve. Instead he decides to stay at school for work. Also, Martin has plans to go camping with Mac (guest-star Kyle Searles). Lastly, a strong-willed and pregnant Lucy is determined to do the cooking and decorating this year.

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.

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!