Eric tries to arrange a romantic evening with Annie, but Annie keeps turning down every attempt he throws at her. At the same time, Annie takes Eric by surprise with the news that she would like to quit college and to start teaching to help get her out of her depression. Meanwhile, Simon is at risk of being fired from his new job at the pizza parlor by his excessive tardiness and discovering that waiting tables takes more people skills than he's equipped to handle. Also, Robbie sets Lucy on a date with one of his friends while Matt is concerned about a woman who keeps showing up at the clinic a lot. Lastly, Mary performs terribly in fire fighting training distracted by her consuming relationship with Wilson.

Lucy and Robbie argue over who should tell Mary about their emerging relationship. Meanwhile, Matt worries that a young woman in his study group might be a victim of physical abuse at the hands of her belligerent boyfriend. Eric's sister Julie shows up at the Camden house with her toddler Erica and annoys Annie as she tries to prepare a lesson for her class. Simon meets up with Sasha and they both try to catch up on their personal lives.

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.