Maya braces for JJ’s high school graduation and departure for college, but tough news from NYU changes everything. Dylan teaches Jimmy a “Dad lesson” as he gets ready for a big job interview. Kenneth pressures JJ to prepare for a grand finale to their time together, and Ray uses his class trip to Catalina to examine his bad luck in love.
When JJ’s attempts to make a good impression on Izzy’s parents fail, he changes course to make a bad one instead. Maya is jealous when Melanie is the recipient of a public display of mom-love. Meanwhile, Kenneth leans on Jimmy for support after a tour of his alma mater reveals a few surprises.
The DiMeos set out for one last “JJ Adventure” before he heads to college, but things get bumpy when the family takes an ill-advised shortcut. Maya and Kenneth’s relationship is tested when they disagree over who knows JJ’s needs best. Meanwhile, Jimmy, JJ and Dylan find fun they shouldn’t be having, and Ray tests his wilderness mettle.
Outraged that JJ's girlfriend, Izzy, declines his invitation to prom, Dylan and Ray swing for the fences with a bold plan to make her jealous. Jimmy, Kenneth and Melanie coach Maya through accepting criticism for the good of her company, and one of the DiMeos takes a big step into a new life.
JJ struggles with spending his new social security benefits strictly on boring stuff. Kenneth uncovers a secret that upsets the status quo in Maya and Jimmy’s relationship. Meanwhile, Ray’s run-in with an old love threatens his chances at a Quiz Bowl championship.
Ray’s attempt to manipulate Maya over an unfulfilled promise of mother-son time backfires when she calls his bluff. JJ tries a new aide after he and Kenneth agree to spend a day apart. Meanwhile, Jimmy’s unsure how to handle Dylan’s teen angst when she invites a boy over.
The DiMeos come together to help JJ shoot a last-minute film for his college application, working against the clock and Maya’s own best interests. Jimmy makes an embarrassing gaffe with JJ’s beloved, and Kenneth and Ray scramble to suppress embarrassing secrets.
When Maya insists that it’s time to meet Izzy, a reluctant JJ arranges a game night for his family and new girlfriend. Ray tries to help on the big night, but his attention to detail puts a major crimp in JJ’s evening. Meanwhile, Dylan and Kenneth let their appetites get the better of them.
JJ’s love-match with Izzy becomes a cage match with Kenneth. Maya and Jimmy dismiss Valentine’s Day as a holiday for suckers until they find a way to profit from it. Unable to find a date to a prepaid romantic night out, Ray brings Dylan.
Maya and Melanie take their promising new fashion line to the 2019 Abilities Expo, only to walk into a room full of familiar and unfriendly faces. Ray accompanies JJ on an overnight college visit. Meanwhile, Dylan’s test scores lead her first to Mr. Powers’ office hours, then to a journey within.
Dylan is horrified to realize people see her as a mini version of Maya, and makes a point to exert her individuality. JJ and Ray each cope with their feelings for shared crush, Izzy. Meanwhile, Kenneth turns to an unwilling Jimmy for help with Joyce.
Maya is less than thrilled when Kenneth interferes with her business plans with Melanie. Ray begs JJ to cast him opposite his new crush, Izzy, in his next movie, which has unexpected consequences. Meanwhile, Dylan is impressed with Jimmy’s band.
JJ challenges Maya’s mentoring tactics when she takes a father and his young son with special needs under her wing. Dylan and Ray attend a teen support group for all the wrong reasons. Meanwhile, Jimmy’s gorgeous new TV sets him on a journey for self-betterment.
Maya lends a helping hand to frenemy Melanie and finds her life taking a surprising turn. Dylan joins the Lafayette basketball team, where her lousy sportsmanship gets results. Jimmy makes up for lost father-son time with Ray.
A Christmas tree fire leads Maya to tell a small lie with big consequences. Meanwhile, Ray struggles to live in Pepper’s shadow as Dylan twists the knife, and JJ encourages Kenneth to stand up to his sisters.
The DiMeos realize they have great intentions but lack follow-through when it comes to … everything. Vowing to change, Ray and Dylan take on government bureaucracy; Kenneth helps JJ prepare for college; and Maya tries to reconnect with Jimmy.
When the DiMeos land in the hospital on Thanksgiving, Maya’s determination to save the holiday leads to an uneasy truce with her rival, Melanie Hertzal; and Jimmy gets jealous when Kenneth bonds with his brother, Billy. Meanwhile, wounds from an old breakup are re-opened, but Ray finds brand-new love in an unlikely place
Seeing the kids believe she exists to solely serve at their pleasure, Maya takes the stage to prove she has so much more to offer. Kenneth finds JJ a job, and JJ finds an unlikely rival. Ray goes undercover informing parents on his classmates’ social lives and gets in too deep.
Seeking a new outlet for her superpowers as JJ prepares for college, Maya sets her sights on a receptive Ray. JJ gets involved in a (too) high stakes poker game, while Dylan discovers what really happens after her bedtime.
Maya’s Halloween becomes truly terrifying when JJ attends a rave in the woods. Ray joins Dylan’s Halloween heist determined to prove he’s more than a do-gooder. Meanwhile, Jimmy and Kenneth turn the DiMeo home into the neighborhood’s haunted house.
Maya must choose between asking her father for money to save their house and a lasting relationship with him. Ray strives to bond with his new British family, only to discover Dylan’s the one with a surprising connection. Meanwhile, JJ shows Kenneth a good time off-the-clock, and Jimmy inadvertently finds love.
The DiMeos cross the pond so Maya can ask her estranged father, the challenging Martin, for a loan to save their house. Meanwhile, Jimmy puts on his “fun dad” hat to ensure JJ has a great trip, Ray digs deep to summon Californian vibes to endear himself to British girls, and Kenneth reveals a love for all things royal.
