Matt begins to go crazy over a psychological evaluation that he is required to take for his medical-school application. Matt also notices the strange demeanor of his psychologist, which leads to a surprising twist. Meanwhile, after Ruthie gets into trouble at school for missing homeroom classes daily, she tricks Robbie into coming to talk to her principal. Simon decides he no longer wants to be together with Sasha since they have nothing in common and that she is not that intelligent, but the plan backfires on Simon. Also, Mike wants to try to be in a relationship with Lucy again, but unfortunately she turns him down since they are both on the rebound from Jeremy and Elaine. Lastly, Eric must convince a terminally ill patient to embrace life no matter what the doctors tell him.

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 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.

When Eric learns that he must undergo double bypass surgery, he calls a family meeting to share the news but loses his nerve at the last minute and decides the group should go bowling instead. His odd behavior surprises everyone, especially Annie who grows more concerned when Eric's brother-in-law Hank shows up unexpectedly. Meanwhile, Robbie pesters Kevin about helping him make a parking ticket disappear. Lastly, Lucy continues to question whether Kevin has ever been with another woman.