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

After coming out of the closet to Honey and Jessica, Nicole struggles with telling Marvin, fearful that her father will be disappointed in her. Meanwhile, Louis wants to manage the Cattleman’s Ranch softball team on his own, so Jessica decides to coach the rival team from The Denim Turtle to prove that she is the superior manager. Chaos is sure to ensue when everyone gathers for the big game at the Greater Orlando Bar and Restaurant tournament.

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.

When Matthew Chestnut returns to Cattleman’s Ranch, everyone but Louis thinks he’s a bad influence, leaving it up to the unlikely team of Jessica, Eddie and Trent to help take him down. While that goes down at the Ranch, Emery and Evan cruise the open water with Marvin and give him a crash course in feminism and etiquette.

Louis starts to fantasize about passing the Cattleman's Ranch torch to Eddie but is worried about his menu choices. Meanwhile, Jessica is still struggling to get on board with Emery's new acting hobby. And when Louis scores a spot on "Who Wants To Be A Millionaire," host Regis Philbin offers Louis and Jessica more answers than million-dollar questions.

Fresh off of a parenting brag to Honey, Jessica finds herself overwhelmed by a heartbroken Evan who wants to spend more time with her. Meanwhile, Emery announces his newfound veganism and faces the wrath of "The Burger Boys" - Louis and Eddie.

When the trusty Huang family van takes a turn for the worst, Jessica and Louis each process the loss in their own way. Meanwhile, the boys take advantage of the opportunity for some bonding time and sneak off on a road trip to find their Washington, D.C., time capsule.

Jessica grapples with her vision of the future as the boys are each realizing what their own goals.