Based in Chicago, the O'Neals appear to be a seemingly picture perfect family, but their lives soon take an unexpected turn when surprising truths are revealed. Eileen is a mom who usually has a fine grasp on all matters under her roof, and her soon-to-be-ex-husband Pat is a good-natured father and the emotional center of the family. Their normal routine at home suddenly gets turned upside down when Eileen and Pat announce their divorce, and their sixteen-year-old-son Kenny reveals to his family that he is gay. Kenny never would have imagined his admission would also result in outing his entire family's secrets, including revelations from his older brother, Jimmy, and little sister, Shannon. Jimmy unapologetically wears his heart on his sleeve and genuinely tries to figure out what's best in any situation, while Shannon is the youngest but carries herself more mature than her age. Life in the O'Neals household wouldn't be complete without Aunt Jodi, Pat's ex-sister-in-law and Eileen's best friend, who is quite the frequent visitor and is also willing to admit things are far from perfect in her own life. What seems like a sudden upheaval that could mark the end of the O'Neals idyllic lives turns out to be the beginning of a bright new chapter when everyone stops pretending to be perfect and actually starts being real.
Following the "coming out" confessions made by everyone in the O'Neal family, Eileen is desperate to control the situation and tries to make Kenny "un-gay". Meanwhile, Kenny tries to find the right time to break up with Mimi and has a heart-to-heart with late-night host Jimmy Kimmel.
Eileen reminds her family that it's Lent and asks them to give up things they really love, which in turn proves to be quite a daunting task. In a chance meeting, Kenny meets his first gay crush, and Pat discovers his little girl, Shannon, is all grown up.
It's Kenny's first day back at school since coming out, and he uses a certain "F word" to describe himself, which then backfires. Meanwhile, Eileen helps Pat choose a couch for his new living space in the basement but she ultimately struggles with accepting this new phase in their relationship.
On the first warm day of spring following an endless Chicago winter, Eileen decides it's time to get a fresh start in her life by applying for her first job since her kids were born. Shannon ultimately overhears her mom's plan and riles up the rest of the family after misinterpreting Eileen's true intentions. Meanwhile, Pat realizes he might not be ready for the single life just yet, even though his patrol partner, Archie, thinks otherwise. And as Kenny wonders who he will date next, Jimmy takes it upon himself to help him explore the newfound world of online dating.
When Pat plans a camping trip to enjoy some father-and-son bonding time with Jimmy, Kenny also joins them to prove that even though he's gay he can still be manly. During the camping trip, Pat continuously pressures Jimmy about his upcoming wrestling match, which leads to a surprising result.
Meanwhile, after Eileen discovers Shannon has been skipping her classes and refuses confirmation, she invites Father Phil over to help answer Shannon's challenging questions she has about Catholicism.
When Eileen's strict, Catholic-abiding mother, Grandma Agnes, arrives unannounced at the O'Neals' home, Eileen has her family cover up both her and Pat's divorce and Kenny's sexuality. Although Eileen wants to keep these secrets hidden so that she can finally win her mother's approval, Kenny tries to convince his mother to "come out" to Grandma Agnes, leading to some surprising twists.
Eileen expects to be shunned by her book club because of gossip about her family, but instead the ladies air out all of their own grievances. Meanwhile, Kenny enjoys visiting a gay coffee shop, but he's displeased when pat joins him for gay dodgeball.
Kenny secures the role of Romeo in a school play, with Mimi playing Juliet. Eileen volunteers to help, believing that it will be the only time she will ever see Kenny marry a girl.
When Jimmy is unexpectedly named Faith Leader for the weekend at the Catholic Youth Retreat, a jealous Kenny decides to take on his older brother's role as ring leader of the bad kids.
Home alone without the kids, Pat invites a new lady friend over, and Eileen can't help but enlist Jodi to spy on them, with surprising results.
When Eileen pushes Kenny to get a job, she starts to feel jealous when he starts to work as a tutor and instantly starts to bond with the student's mom. As Kenny starts to spend more time away from home, Eileen realizes she'll need to make some changes if she wants her relationship with Kenny to improve. Meanwhile, Pat wants to bond more with the kids but makes some questionable choices in trying to become the fun parent.
After realizing Pat left his police badge at home, Jimmy convinces Kenny and Shannon that he should use Pat's badge to pretend he's a police officer so they can receive free perks around town. Meanwhile, when Pat tells Eileen about an upcoming date he's going on, she takes matters into her own hands when it comes to a potential suitor in her dating life.
As the school prom approaches, Kenny tries to think of who the best guy would be to ask as his date. With time running out, Kenny and Jimmy try to come up with the perfect "prom-posal" for the classmates they each have set their sights on. Shannon thinks the idea behind prom is a scam and would rather stay at home, but once Pat discovers she was asked to attend, he tries to convince her to go. Meanwhile, Eileen tries to keep VP Murray's romantic attention at bay but struggles to resist.