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.
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.
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.
When Maya learns JJ attempted to run away, she is determined to help him complete the task as any able-bodied person could, but her actions exasperate JJ, as he longs for independence. 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.
Maya and Kenneth work together to hold JJ accountable for his academic future when he cheats on an exam at school. Meanwhile, Ray gets into a get-rich scheme.
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.
Dylan asks Maya not to have their annual birthday party for her, but Maya holds an amazing surprise party anyway and soon learns the real reason why Dylan didn't want to have a party. Elsewhere, Ray is put in charge to watch JJ but panics when his brother has a day of independence at the mall to buy Dylan a birthday present while Jimmy and Kenneth struggle to find something they have in common.
When the Dimeos throw their annual Oscar party with other special-needs families, Maya feels threatened by new mom Becca, who seems a little too perfect. Meanwhile, Jimmy encourages the fathers at the party to let loose while Ray tries to impress a girl by pretending to be someone he is not.
JJ gets into an argument with Kenneth over their time together while Dylan decides she must “parent-trap” them both so they can get back together. Meanwhile, the family gets a chance to be members of a country club for a week. Ray sees it as a chance to live the high life while Maya jumps at the chance to spend mother-and-son time
Maya attempts to give Jimmy a Valentine's Day gift, with the help of his old roommate and her ex-fiance. Meanwhile, Ray is elated to find out he has a secret admirer and JJ i in charge of distributing candy-grams, which proves challenging for both him and Kenneth.
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.
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.
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. Meanwhile, Jimmy attempts to continue his tradition of spending no money on vacation while Dylan becomes anxious after visiting a fortune teller. Back at home, Kenneth has trouble fitting in at school while JJ is away.
It’s Christmas time at the DiMeos, and 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. Worrying he won’t get into college, Ray joins the choir and gets a coveted solo. But when a very attractive new teacher is hired, JJ decides to join his brother and takes Ray’s solo.
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 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.
The DiMeo plan to avoid another horrible Thanksgiving with Jimmy’s brother’s family backfires when they invite themselves over to celebrate. While Kenneth and Ray destroy the turkey, the rest of the family creates a game, checking off the various instances of annoyance their relatives are known for. When Jimmy and his brother Billy decide to take their competition to the streets, the family discovers that Billy’s family is not as perfect as it seems.
JJ meets a new girl at school, an injured gymnast, who must learn to adapt to school life in a wheelchair. JJ shows her the ropes and soon forms a crush. Elsewhere, Ray saves face by claiming a picture of his own nipple on his phone to be a ”sext” from his ”girlfriend.” The plan makes him a hero among the boys at school, but backfires after Maya learns the whole story. Meanwhile, Jimmy teaches Dylan how to properly deal with stress.
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 while Kenneth is scared of losing his job when JJ gets drunk at a party. Even though Maya is furious, she is thrilled to see JJ having a “normal” life.
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 paintballing. But can she let herself have fun without JJ?
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.
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.
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.
