On Valentine’s Day, the mood is anything but romantic as Jessica competes with Louis to see who can give Evan the best advice on how to celebrate with new girlfriend, Sicily. Eddie asks Honey for help to find out who his secret admirer is after he’s passed a love note on a Cattleman’s delivery run.

Eddie begins dating Trent's sister Tina but it puts a strain on his friendship with Trent. When Evan fails his physical education test because he can't run, he turns to Jessica for help, but she's even worse at running than he is. Meanwhile, Louis is thrilled when the restaurant gets the Golden Prune award as being the best place for seniors to dine, but the honor doesn't reap the results he expected.

Louis tries his best to convince Jessica to consider early retirement, but she’s having none of it. When Eddie looks for advice on how to be a better person for Tina and win her back, he ends up watching her favorite TV show, “Sex and the City,” for clues.

Jessica starts her college classes, leaving Evan in charge at home as “vice mommy.” But the transition doesn’t go smoothly, either for her starting school again or with Evan taking over the reins of the Huang household. Eddie and Louis run into conflict when Eddie just wants his dad to treat him as an employee, and not a son, at Cattleman’s Ranch.

Eddie faces his fears and finally introduces his girlfriend, Tina, to his mom.

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