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.

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.

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.

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.

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.

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.

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.

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.

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.