In last season's finale, Simon returned home from college and realized he still had feelings for Cecilia; Matt's marriage was tested when old feelings for his ex-girlfriend (guest-star Andrea Ferrell) resurfaced; and Eric and Annie became grandparents when Mary gave birth to her first child.

In the ninth season premiere, Simon appears to be getting extremely close to his new girlfriend, Georgia (guest-star Rheagan Wallace), causing Eric and Annie to suspect they are having sex. Meanwhile, Kevin worries that mother-to-be Lucy may be in denial about her pregnancy when she refuses to go shopping for maternity clothes. Also, Matt returns home for a visit and is instantly pulled into the family drama. Lastly, Ruthie and the twins find themselves in a heap of trouble on their first day of high school and kindergarten, respectively.

Simon is reluctant to talk to Eric and Annie about his relationship with Georgia (guest star Rheagan Wallace). However, he eventually drops the bomb that they are having sex and that he's currently on academic probation for skipping classes to be with her. Meanwhile, Simon's situation helps Eric realize that the church should teach teens the importance of abstinence and he asks Lucy to lead a class on the subject.

Also, Lucy and Kevin learn the sex of their baby, and Lucy starts to question her ability to be a good mother. Matt is worried that Martin is still broken-hearted over Cecilia and will tell her about Simon's new relationship with Georgia. Lastly, Matt chips away at Ruthie's unwillingness to apologize to Martin.

Although she is worried about the lesson plan for the class she is teaching on abstinence, Lucy is excited when Eric tells her she is now the Associate Pastor and will soon give her first sermon. Meanwhile, during Simon's visits with Dr. Gibson (guest-star David Piel), he confesses that he has been using his relationship with Georgia (guest-star Rheagan Wallace) to block out the guilt he still feels about the fatal traffic accident. Lastly, Ruthie falls for a guy she meets in detention, Harry (guest-star Aaron Carter), a foster kid currently living in a county facility, despite Martin's reservations.

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.

Simon's ex-girlfriend, Georgia (guest-star Rheagan Wallace) tells Simon she's supposedly pregnant and Simon doesn't know how to tell his parents---but Georgia is not being completely honest. Eric, Annie and the twins are on a road trip from Ginger's house back to Glen Oak and reminisce on old times. Meanwhile, Matt rushes Lucy to the hospital when she collapses at the grocery store. They can't track down Kevin as he is working on a drug bust. Lastly, a lonely Ruthie is having a miserable time in Puerto Rico with Mary, Carlos and baby Charles and calls home for comfort.