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.
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.
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
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.
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.