Set in the '90s after his moment of fame has passed, Ted is forced to enroll in high school with his best pal John, experiencing the highs and lows of teenage life.
John and Ted use a phone in the school basement to call a phone-sex hotline; when the charges end up costing the school thousands of dollars, a hard-nosed special investigator from the school district is brought in to find the culprits.
Ted starts a risky affair with a married woman and becomes emotionally invested; Matty and Susan try to figure out the cause of Matty's erectile dysfunction.
A weed shortage forces John, Ted and Blaire to complete a drug dealer's Dungeons & Dragons campaign; unaware that the reward is a bag of pot, Matty and Susan join the quest.
When Blaire and her girlfriend break up, all she wants to do is sit on the couch and watch rom-coms, to Matty's frustration; Ted's lie to John about hooking up with their elderly neighbor leads the boys to an unusual double date.
Realizing John is light on extracurricular activities for college applications, John and Ted audition for the school play; Matty and Susan get part-time jobs at Dunkin' Donuts.
After a meaningless hookup, Blaire finds herself navigating an unexpected pregnancy, causing a clash of opinions among the family.
When a police officer finds John and Ted's weed during a traffic stop, Susan takes the fall for them and gets a 10-day jail sentence; she navigates life on the inside, while the family discovers what life on the outside is like without her.
After a health scare, Matty is under doctor's orders to keep calm; this becomes especially challenging when the O.J. Simpson verdict is announced, leading the family to go to extreme lengths to keep him from learning the truth.
Ted’s attempt to get expelled from high school leads him to purchase drugs from an unlikely source.
Ted and John’s plan to exact revenge on the school bully inadvertently puts them in a parental role. Matty agrees to get a colonoscopy… on one condition.
Ted and John go to extraordinary lengths so that John can watch his first adult film. Matty and Susan’s disappointing night out leads Susan to question their relationship.
Ted’s plan to spend Halloween with John is thwarted when Blaire forces him to be her designated driver for the night. Susan tries to cheer John up by finding him a new friend.
Blaire convinces Matty and Susan to let Ted act as their marriage therapist. After the session, Ted, John and Blaire encourage Susan to pursue the career she abandoned long ago.
Matty’s unorthodox Christmas wish is granted, completely upending the Bennett family dynamic. A trip to church gets John and Ted wondering about Ted’s miraculous origin.
As the end of the school year approaches, Ted plots to help John lose his virginity after John learns he is the last virgin in school.