While Grandma Jenny, Emery and Evan look to the future, Louis and Jessica take a trip down memory lane. Eddie, on the other hand, is stuck trying to navigate the present after his first college visit doesn't go according to plan.
- Be Careful What You Wish For: Grandma, Emery, and Evan eventually get into a spat about how their interests don't align, and separate to try and follow their own dreams. However, Grandma grows tired of the DeVito impersonator using her credit card to buy fancy clothes, Emery attends a live taping of a sitcom but has to fake laughter after fifteen successive retakes, and Evan attempts to solicit political advice at a muscle beach (trying to follow in the footsteps of Governor Arnold Schwarzenegger) and finds that everyone there is just focused on their own fitness. They all reunite after and decide that maybe they should go back to focusing on the present while they're all still together.
- Celebrity Impersonator: While in Hollywood, Grandma Jenny ends up hooking up with a Danny DeVito impersonator that she thinks is the real deal. In the Where Are They Now epilogue, he quits after Grandma breaks his heart and becomes a bodyguard for Governor Arnold Schwarzenegger.
- Didn't Think This Through: Towards the end, Emery and Evan realize there's a possibility that Y2K won't cause a bug that wipes out their now-gigantic credit card bills. Grandma just brushes it off by saying she's already faked her death in the past.
- Former Teen Rebel: It's revealed that Jessica was one in her youth, even gaining the nickname "Messy Jessie" for filling an exercise ball with cream and using it as a giant water balloon.
- Generation Xerox: In order to get Eddie to reconsider attending a college after an Incredibly Lame Fun experience dissuaded him from them entirely, Louis tells Jessica that she needs to be the one to talk with him because of their similarities. When Jessica protests, stating that Evan's the one most like her, Louis retorts that Evan's most like her currently and Eddie embodies the free spirit that she used to be at his age.
- Gone Horribly Wrong: Jessica is steadfast in making sure Eddie doesn't blow his chance at going to college after paying Kareem Abdul-Jabbar (first met by the Huangs in "Fresh Off the RV") for a recommendation, keeping him focused on studying and away from a campus party. However, when it's time for the interview with the dean of admissions, Eddie purposely blows it because she convinced him it would be too boring.
- Hard Work Hardly Works: When the Huangs arrive at UCLA, they try to stay with a relative at the dorms, and learn that his roommate is being sent home to work at his family butcher shop because he failed an exam even though he had been valedictorian at his high school. This just convinces Jessica that UCLA is a higher-tier school than she had considered.
- Hypocrite: A chunk of the main plot is dedicated to how Jessica used to be known as "Messy Jessie" when she went to college, and how she doesn't want Eddie to follow in her footsteps (particularly not wanting him to need to go back to school later in life like she's currently been doing), which she fears makes her come across as hypocritical. Both Eddie and Louis state that he won't, because Eddie has something that Jessica never had: Jessica for a mother.
- Incredibly Lame Fun: Because Jessica forbade him from a campus party, the only entertainment Eddie is able to find on-campus is a bunch of students alternating between watching a tiny TV for hours and taking naps. It bores Eddie to the point that he tanks his interview with the dean, then tells his parents they should be grateful for not having to spend thousands on tuition when Eddie might not enjoy any college at all.
- Millennium Bug: Due to thinking that this will lead to all of their finances being erased, Grandma, Emery, and Evan decide to spend the day living their wildest dreams in Hollywood.
- Shout-Out: At the start of the episode, Eddie keeps envisioning whether or not he should go to college as the pill scene from The Matrix, followed by Jessica throwing textbooks at him in slow-motion.
- Where Are They Now: In a parody of coming-of-age college movies, the episode ends with brief descriptions of what happened to a few characters in the following weeks, with a medicine ball used to coat Louis in cream listed as "deceased".
