In hopes of finding a better educational environment for their special needs eldest son JJ, the DiMeo family moves into a new neighborhood where Maya tries to make sure that JJ is looked after at his new school.
Maya regrets hiring Kenneth as JJ's aide after JJ accidentally misses his physical therapy session, but she later sees that Kenneth is doing a good job with JJ. As Ray tries to get close to Jillian, Jimmy runs into trouble with the neighbors.
When the football team invites JJ to their annual pre-game bonfire on the beach, things take a turn when Maya makes the school cancel the event, because of her worry about JJ's safety. Jimmy and Ray try to get rid of the junk that is taking big space in the house.
After being seen as an inspiration, J.J. and Kenneth take advantage of the situation by enjoying the perks that come with it. When the DiMeo family have fun together without JJ, Maya feels guilty that JJ wasn't there with them.
When the kids are no longer interested in doing the family's traditional activities on Halloween, Jimmy gets upset. But Maya tries to make him do something fun. Dylan helps Ray with the school's Halloween event, while Kenneth gets into trouble after taking JJ to a party.
When a new girl, Claire, arrives in school, Kenneth tries to set JJ up with her, but JJ thinks that they're only friends. Ray attempts to get popular at school by resorting to desperate measures. Jimmy tries to help Dylan deal with her anger issues.
When Jimmy's brother and his family come for a visit on Thanksgiving, Maya sets out to teach them a lesson because of their irritating behaviors. Ray and Kenneth try to take over the cooking task, even though they don't have any skills.
As Ray helps JJ express his feelings for Claire, his plan backfires when she turns JJ down. Ray tries to make his family take him to school on time so that he won't miss his upcoming school trip.
When JJ goes with Jimmy to the local ice rink, he becomes interested in playing hockey, but he has to persuade the family that it's safe to play. As Maya and Kenneth bond, Ray and Dylan have an argument.
As the family is preparing the Christmas festivities, things take a bad turn when their van gets stolen. JJ joins Ray on the school choir in order to make their resumes look better for college.
As the family goes on their traditional annual road trip, Ray sets out to make them follow his own directions. As Kenneth tries to hang out with his old friends, they avoid him because he's in a different place now.
The DiMeos resort to desperate measures in order to impress their insurance agent, so that he would help JJ. Ray enlists JJ's help with his school contest's essay.
The DiMeos become on high alert as Maya and Kenneth fall ill, and the rest of the family works together to look after each other. JJ helps his sister with a boy she has a crush on.
As Valentine's Day arrives, Maya attempts to spark some excitement into her relationship with Jimmy. A misunderstanding leads Ray to falsely think that he has a secret admirer, and Dylan takes advantage of the situation. JJ tries to resist his candy addiction when he's tasked with delivering candy-grams.
As the DiMeos head to a luxury country club, Maya resorts to lying in order to enjoy the fancy stuff there. JJ decides to use a computerized pad to replace Kenneth after they clash with each other.
As the family is preparing for their annual Oscar party, Maya butts heads with the new member Becca, who seems to have a perfect life, while Kenneth comes up with interesting questions in the movie trivia game.
In spite of Dylan's objection to celebrating her birthday, Maya sets out to throw her a surprise party. Ray gets worried when JJ goes out on his own at the mall. As Jimmy and Kenneth try to get along, their plan backfires.
Tension rises between Maya and Ray after Maya hits a car. Jimmy and Dylan look for a rare item at the supermarket. The family finds out about Kenneth's other secret job.
After Maya and Kenneth find out that JJ has been cheating on his tests, they try to teach him to rely on himself. As Ray tries to make quick money, Jimmy helps him out when he lands in trouble.
After JJ overhears his parents saying that he can't look after himself on his own, he runs away to Kenneth's place. Maya tries to make JJ behave like a normal young man. Dylan tries to help Kenneth relive his former college glory when he was a popular athlete.
Maya and Jimmy make a surprising discovery after they have the house to themselves when the kids go out on prom night. Ray is forced to put his beliefs to the test after he speaks with his dream girl. JJ tries to escape from the party to hang out with unexpected company.
As summer arrives, JJ goes camping but has a minor injury that requires surgery. Jimmy enjoys special treatment at the hospital, while Dylan makes a surprising discovery about her running skills.
During their trip to JJ's camp, Jimmy and Dylan bond together, Maya runs into a surprise at the airport, while Ray tries to discover new things about himself.