It’s the first day of high school and Eddie wants to join the football team to impress girlfriend Alison, despite Jessica forbidding him to try out. Emery finds out that Evan has been moved up a grade and is in middle school with him. Louis battles with Kenny Roger’s right-hand man over changes at the steakhouse

When Michelle Kwan comes in second place at the Olympics, Jessica tries to keep it from Emery and Evan, only to get caught up in an elaborate conspiracy theory that leads them seeking answers from Nancy Kerrigan. Meanwhile, Louis changes Eddie's bedtime to spend more quality time together watching Letterman, but feels slighted when Eddie spends his newfound free time elsewhere.

Louis is crushed to find out that Matthew Chestnut is quitting the restaurant to take a job at Dollywood. Louis ends up hiring Eddie’s friend Trent, which doesn’t sit well with his son. Meanwhile, Jessica does everything she can to appease Amy Chestnut in order to get her job as PTA president; and after telling a joke and getting a laugh from Emery, Evan deludes himself into thinking that he’s the funnier brother.