Beverly surprises the family with an end-of-summer vacation to Miami with the flight down resembling the classic film, and Geoff accidentally spills to Erica the real reason for the trip.
Adam returns to William Penn Academy as a senior and wrestles with the fact that he is a cool kid and no longer a nerd while his original friend group isn't as lucky. Meanwhile, Beverly attempts to have a more grown-up relationship with Erica and Barry before they head back to college.
Geoff and Erica come to a point in the relationship where they realize they are in different places in college; and Geoff makes an important decision while Beverly tries to find a new purpose in her life as she seeks political office as the city comptroller.
Bill is getting married and Beverly and Jane have only 24 hours to plan it; a fortune teller at the wedding reception could change the future for Adam, Erica and Barry's romantic life.
Beverly's meddling in Adam's relationship with Brea leads to a confrontation with her divorced mother, Vicki. Meanwhile, Barry struggles to reunite the JTP following his breakup with Ren.
Adam sets out to create a movie that will tackle racism but realizes he is out of his depth on the subject due to his sheltered upbringing. Meanwhile, Geoff is determined to teach Erica and Barry to become better people.
Pop-Pop surprises the family with an ill-advised winter cruise to Canada, while Erica stirs up holiday trouble at home.
Inspired by his obsession, Adam helps Beverly plan a hug mystery party for the family. Meanwhile, Erica, tasked with declaring her major, bumps up against Barry's cockiness as she considers going the pre-med route.
Beverly enlists the help of Erica, who has recently declared pre-law as her major, to sue her cookbook publisher after finding her book in the bargain bin at a bookstore. Meanwhile, Adam and Pops bond while taking a trip on the wild side after Adam convinces Pops to fall back into some youthful adventures.
When Beverly realizes that she and Murray are not quite as in sync as they once were after a game night with the very-much-in-love Dolores and Bill, Beverly convinces Murray to get a hot tub to spark romance and spend time together. Over at college, Geoff decides to try out a new look for himself, which is not well received by Barry, causing some of Barry's personal insecurities and fears to rise to the surface.
After realizing how little time Adam has left at William Penn, a sentimental Beverly decides to get more involved at the school, to Adam and Principal Ball's dismay. In order to prevent her from intervening with Senior Skip Day, Adam and Principal Ball team up to put Beverly through an intense Quaker Warden training, which ends up backfiring.
Beverly enlists the help of Barry and Erica to teach Adam to be more assertive, but Adam feels guilty after taking it too far. Meanwhile, Murray resolves to be a better friend after learning that Vic doesn't think he can confide in him.
As William Penn's new Quaker Warden, Beverly is thrilled to have co-workers for the first time and sets out to make them all love her. To her dismay, it's more difficult to win them over than she anticipated, as her reputation of being a difficult school parent precedes her. Meanwhile, Geoff competes in the "Mr. Ships Ahoy" beauty pageant to prove to Erica that he can be seen as desirable by other women.
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.
When the NFL players go on strike and the football season is threatened, Barry gets concerned that he and Murray will no longer have anything to talk about which leads Barry to try out for the Eagles team himself. Against Erica's advice, Beverly decides to start selling a nutritional product from a sketchy company in an attempt to gain financial independence.
When Barry and Joanne crash Erica and Geoff's peaceful weekend camping trip, they end up in a competition to see who is the better couple, causing some unexpected shifts in relationships. After learning that Brea thinks Adam has an easy, privileged life, Adam seeks to prove her wrong by getting a job but quickly learns she might be right.
After realizing there may be trouble in lovers' paradise for Erica and Geoff, Beverly involves herself in their relationship as well as Barry and Joanne's to make sure everyone stays together. Meanwhile, Adam and Brea are cast opposite of each other in the school play, but their excitement for one another's success grows dim when one starts to outshine the other onstage.
Trying to move on from their breakup, Erica goes on a date with a guy from the coffee shop while Geoff ends up on an episode of "The Dating Game", which winds up making things even more difficult for them both. Meanwhile, Beverly is thrilled to learn that Murray has spontaneously purchased a shore house until she realizes it's not quite the luxury home she imagined.
Following Erica and Geoff's breakup, Murray decides to take Erica out on a daddy-daughter date to cheer her up. Meanwhile, Adam is excited to participate in the school senior prank until his conscience catches up with him and he enlists Beverly's help to get him out of it.
In order to take her mind off of her heartbreak, Erica takes a trip to Los Angeles to see her best friend, Lainey Lewis, and they end up getting the band back together for a gig. Meanwhile, after getting caught taking part in an underground poker game, Adam gets sentenced to Pop-Pop duty, which turns out better than expected.
Erica fears that Geoff has moved on from their breakup and started dating someone else. Meanwhile, Adam decides to find Dave Kim a date to prom, once he remembers his pact with Dave that they won't go to prom if they both don't have dates.
Geoff shares with the JTP that he is planning on asking Erica to marry him and gives them the engagement ring for safekeeping. Like any good romantic comedy, several miscommunications and misunderstandings between Geoff and Erica's friends and family result in a potential derailing of the proposal, forcing Adam to step in to keep the couple's special moment alive.