Maya DiMeo moves her family to a new, upscale school district when she finds the perfect situation for her eldest son, JJ, who has cerebral palsy. While JJ and daughter Dylan are thrilled with the move, middle son Ray is frustrated by the family's tendencies to constantly move, since he feels his needs are second to JJ Soon, Maya realizes it is not the right situation for JJ and attempts to uproot the family again. But JJ connects with Kenneth, the school's groundskeeper, and asks him to step in as a his caregiver, and Ray manages to convince Maya to give the school another chance.
Maya struggles as Kenneth takes over as JJ's full-time aide. Loving his new freedom, JJ avoids attending a physical therapy appointment, and Maya automatically blames Kenneth, using any excuse to confirm her misgivings and moves to fire him. Meanwhile, Jimmy struggles to teach Dylan the family way to not be so neighborly.
While JJ finds success at school with a group of friends, Maya forces the cancellation of the homecoming bonfire, concerned that the beach location is not wheelchair accessible. Soon, the students speak out against JJ. But when Maya realizes she was wrong, the two stage a fake prank to encourage his classmates to have a change of heart. Meanwhile, Jimmy helps Ray settle into the new home.
Exploring the city on their own, JJ and Kenneth realize strangers look at them as inspirational. The two push their luck, receiving free food and baseball game admissions. Kenneth lets this get to his head, goes overboard, and things fall apart. Meanwhile, as the family can't do anything without having to worry about wheelchair accessibility, Dylan and Ray convince Maya to take them paint-balling. But can she let herself have fun without JJ?
Jimmy is upset the kids no longer want to participate in the family tradition of dressing up for Halloween. Maya tries to cheer up Jimmy by allowing him to do things he loves by taking things off the family "Dead to Me" list. Meanwhile, Ray recruits Dylan to help work the school's haunted mansion, and Kenneth is scared of losing his job when J.J. gets drunk at a party. Even though Maya is furious, she is thrilled to see J.J. having a "normal" social life.
J.J. meets a girl his age who is temporarily wheelchair-bound due to twisting both her ankles in a gymnastics accident, so Kenneth tries to fix them up despite J.J.'s insistence that the girl isn't interested in him that way. Meanwhile, Ray takes an embarrassing photo of his nipple, then tries to pass it off as a girl's nipple to some classmates, hoping he can become popular for receiving a "sext". Also, Jimmy tries to help Dylan deal with anger management, after Dylan destroys a participation trophy in the school display case because she despises what it stands for.
Maya wants to make a game out of Jimmy's brother Billy and his family's annoying habits when they visit for Thanksgiving, but everyone else worries that this will cause more family drama than necessary. Meanwhile, Ray and Kenneth take over Maya's annual dinner preparation despite their combined lack of cooking experience.
Maya enlists the family to assist JJ in romancing a girl at school, but it backfires when JJ expresses his feelings to Claire, and they are not reciprocated. Meanwhile, as the DiMeos are always late, Ray has the family practice to get to school in time for his upcoming weekend field trip.
JJ instantly wants to join a sled hockey team made up entirely of people with disabilities, but Jimmy is not thrilled and thinks it's dangerous. Meanwhile, Maya takes a CPR class with Kenneth, and she sees how popular he is and realizes that she needs to be nicer in order to keep him as JJ's aide.
Maya surprises everyone by embracing a newfound holiday spirit, but her view is put to the test when the family van is stolen along with all their holiday gifts. Ray joins the choir and gets a coveted solo. But when an attractive new teacher is hired, JJ decides to join his brother and takes Ray's solo.
The family goes on an annual impromptu family road trip, but Ray has something in store, which angers Maya when she finds out what it is. But Maya's relentlessness proves to be helpful when she takes control of an emergency situation involving Ray's appendix.
In order to get on the good side of their insurance agent to get everything JJ needs, the DiMeos have Dylan make a tough sacrifice at her track meet. Meanwhile, Ray wants to use his brother for inspiration while writing for an essay contest at school, but JJ rejects his plan. But when another student lies using the same plan, Ray and JJ team together to outdo the other student.
Dylan becomes Kenneth's replacement for JJ when Kenneth also gets sick. Jimmy ends up doing well with Maya's normal duties, but he tries to keep it from her to avoid her feeling bad. Meanwhile, JJ protects Dylan from a boy she's interested in. And despite its illness, the family bands together and pulls an all-nighter to finish Ray's school project.
Maya gets help with Jimmy's Valentine's Day gift; Ray is excited about the prospect of having a secret admirer; J.J. distributes candy-grams.
J.J. argues with Kenneth about their time together; the family become members of a country club for a week.
Maya feels threatened by the perceived perfection of one of the mom's at her annual Oscar party; Ray pretends to be someone he's not to impress a girl.
Maya plans a surprise party for Dylan's birthday even though Dylan herself is adamant about not having one. Meanwhile, Ray is unnerved by a trip to the mall with JJ to buy their sister a present; and Jimmy and Kenneth realize they have nothing in common.
After leaving a note behind Maya's back, Ray takes sides against the family when Maya dings a nearby car. Following through on a promise, Jimmy and Dylan share a moment, as father and daughter are on a search in the back room at the local supermarket while JJ teaches a rude customer a lesson, and a moonlighting Kenneth hides his side job from the DiMeos.
Maya and Kenneth team up to hold JJ accountable after he cheats on an exam at school. Meanwhile, Jimmy bails Ray out of a get-rich-quick scheme, but also learns the reason behind his need for some fast cash.
When Maya learns JJ attempted to run away, she is determined to help him complete the task as any able-bodied person could. Meanwhile, Jimmy struggles to have hard talks with the kids without Maya, and Dylan tries to get Kenneth to revive his glory days as a high school sports star.
It's prom night, and all three DiMeo kids are going, which leaves Maya and Jimmy with a rare night to themselves. Kenneth is shocked to learn that they like to spend their nights without the kids to bring up past arguments they have bottled up or ignored in the past. Later at school, Ray thinks he is finally about to have his first make-out session with a girl, but learns differently when she uses the "R" word. Meanwhile, a wary JJ bonds with someone who is sick of being the center of attention at school functions.
With the school year over, Maya is excited to spend the summer with JJ, but he and Kenneth have other plans. Meanwhile, Jimmy gets special treatment at the most unlikely of places, while Dylan's identity in the family is threatened.
As the family readies for their flight to JJ's camp, Maya gets a surprise at the airport. Ray sees the summer as an opportunity to reinvent himself, while Jimmy and Dylan turn the trip to camp into a father/daughter bonding moment.