When The Ottoman Empire’s business declines due to a new furniture competitor, Adam offers to make Murray a commercial starring Marvin, but things go awry when Marvin’s actions mess up the original plan. Meanwhile, Beverly offers to help Barry as he keeps striking out as he attempts to get a girl at school.

Erica tells Beverly she is going to spend the first night of Hanukkah with Geoff and his family; Beverly worries and starts a competition for who hosts the best Hanukkah party; Barry seeks advice from Pops on how to be cool.

The Goldbergs-inspired special event picks up at William Penn Academy in the 1990s as now Head of School John Glascott leads a faculty of teachers with wildly different views on how to mentor students and recruits his tough-as-nails-sister Lucy to join his staff and enroll her teenage daughters, Felicia and Gigi, as new students.

Hoping to get the true spring break experience, Erica and Barry visit Pops in Florida, yet it’s nothing how they expected. Meanwhile, Adam tells the truth to Beverly and Murray but then gets a surprising reaction.

Adam discovers Beverly has been manipulating him with guilt letters when he tells his mother he doesn’t want her to chaperone the school trip to Hershey Park. Meanwhile, after attending Career Night, Geoff realizes he doesn’t want to be an eye doctor like his father.

Adam’s obsession with toys is cause for concern for Beverly and Murray, and they try to distract him with a new hobby. Meanwhile, the Dropouts’ decide to audition for “Star Search,” but their egos threaten the band’s future.

Beverly decides their street needs another stop sign and pleads her case to the city comptroller. Barry panics when he realizes he's neglected his college applications, but the situation only gets worse once Murray is involved. Meanwhile, Erica struggles with her career choice.

Adam is thrilled when he has to design his own video game for school, so he turns to his family for inspiration. Meanwhile, Beverly is worried about Pops’ gambling and ropes Bill Lewis into her latest scheme.

Adam gets a surprise from his past -- his first love Dana; Barry and Erica are off to college, but realize they have nowhere on campus to live.

Barry decides to rush a fraternity; Beverly and Murray get closer to being empty nesters.

As Adam's girlfriend, Brea, heads to visit her cousin at the University of Virginia (UVA), Beverly projects her own insecurity onto Adam, convincing him to do a grand gesture to prevent Brea from choosing UVA for college. Meanwhile, when Geoff asks Erica to go to the local Nancy Glass talk show with him, a disappointed Barry teams up with Geoff's sister Joanne to change his mind.