When Eileen's strict, Catholic grandmother, Agnes, makes a surprise visit, the family attempts to hide Eileen and Pat's divorce and keep Kenny's sexuality a secret.

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.

VP Murray is nervous to tell Pat about his plans to ask Eileen to marry him and is relieved to receive Pat’s blessing to do so. Meanwhile, Eileen and Kenny realize how far they’ve come when they help Allison deal with her close-minded parents. Shannon and Jimmy discover a pregnancy test and prepare for life with another sibling.

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.

When Jimmy recruits a reluctant Kenny to join his wrestling team for a one-time match, a surprise victory gives him the confidence to join the team full time to become the first, openly gay athlete at St. Barklays. Kenny’s newfound stardom makes Jimmy feel a bit replaced, but when an opponent refuses to wrestle his brother, Jimmy puts his feelings aside and rallies the team around Kenny. Meanwhile, Pat injures his back trying to help Eileen prepare for a weekend getaway, but things only get worse when she tries to be the perfect caregiver to impress VP Murray but fails miserably.

Kenny has a difficult first day at school after having come out.

When Kenny, Jimmy and Shannon head back to school, Kenny decides to start the first LGBT club at St. Barklay’s in honor of National Coming Out Day. After only recruiting one meek lesbian named Allison, Kenny pressures her into coming out to her family and ultimately realizes everyone’s journey isn’t as easy as his own. Meanwhile, Eileen realizes she might have real feelings towards VP Murray, unfortunately Pat also befriends him, which leads to an awkward situation.

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.

Eileen faces her book club for the first time after her family’s “outing,” but things take a surprising turn when instead of shunning her the ladies begin opening up – way too much – about their own problems. Kenny’s first trip to the “gayborhood” coffee shop is everything he’d hoped for, until Pat tags along with him to a gay dodge ball match.

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.

Eileen will stop at nothing to win the Christmas choir competition and gives the coveted Christmas choir solo to their newest member, Brett, to Kenny’s dismay, while Jimmy is tasked with spying on their toughest competitor, Sheila Demars. But, when Kenny attempts to sabotage Brett’s role, he finds a potential love interest. Meanwhile, Shannon accidentally gives Pat the wrong impression about a Christmas present she plans on giving to Ethan.

When Halloween arrives, or what Kenny refers to as “the gay Super Bowl,” he plans to go to Boystown to watch the festive costume parade. In an effort to prevent Kenny from attending, Eileen agrees to let him throw his own Halloween party at home. Eileen’s tolerance is ultimately tested when Kenny recruits Stuart and his gay friends to join the big party, and he makes a BIG costume change. Meanwhile, Jimmy and Shannon plan to pull off an epic Halloween prank.

When Kenny decides to audition for the school play, “Zombie Romeo and Juliet,” Eileen volunteers to help out. Kenny receives the role of Romeo, but much to his dismay, his ex-girlfriend Mimi is playing Juliet. Things get more awkward when Eileen, realizing that this may be the only time she will see Kenny marry a girl, begins to treat the play’s wedding scene like an actual wedding. Meanwhile, Pat and Jimmy both struggle to talk to their new crushes.

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.

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.

When VP Murray starts spending time around the house, Pat realizes it’s time to move out. Meanwhile, Eileen starts her new job at Aunt Jodi’s salon, and when the kids discover how unhappy their parents were during their 18 years of marriage, they stage a celebratory “divorce ceremony”.

We step into the O’Neals’ messy dating lives as Eileen and VP Murray’s secret dating life is about to be unraveled, Kenny jumps into the world of gay dating apps but feels discouraged after not getting enough swipes to the right, and Jimmy goes too far to declare his love for Lacey. Meanwhile, Aunt Jodi meddles with Shannon’s love life after mistakenly thinking she needed her help.

The O’Neals deal with a change to their Thanksgiving tradition when Pat and Eileen invite Gloria and VP Murray to dinner as their dates. Meanwhile, things don’t go as smoothly planned when Gloria offers to help Kenny cook, and Eileen prepares to meet VP Murray’s mom for the first time.

Pat’s brother Dwayne (who is also Aunt Jodi’s ex-husband) comes to town to help Pat build his new “tiny house” in the garage. Shannon realizes Jodi and Dwayne still have chemistry, and tries to get them back together. Meanwhile, when Eileen becomes addicted to a CrossFit class she’s taking with Kenny, he must find a way to break the cult-like hold it has over her.

After Kenny and Brett officially become a couple, Kenny starts to think of plan on how he should break the news to his parents. Meanwhile, Jimmy surprises everyone when he scores a high SAT score, forcing Eileen to hold up her end of a deal that she had previously made and takes Jimmy car shopping.

Jimmy wants to teach his younger brother the rite of passage of drinking. When Shannon gets a comp hotel room due to a scam she’s pulling, Jimmy thinks this is the perfect time to teach Kenny how to drink, but it all goes awry when Kenny invites Brett to join in. Meanwhile, Eileen discovers that Pat has a new girlfriend, her nemesis, Sheila DeMars.

When Kenny convinces VP Murray to hire a gay teacher, Kenny’s loyalties are tested when the teacher starts to make Jimmy’s life miserable. Meanwhile, when Pat’s courteous nature robs him of a winning lottery ticket, he decides to stop being such a nice guy with Shannon’s help, which doesn’t bode well for Eileen, who needs Pat’s help hosting a dinner for the Bishop.

Eileen and Pat’s divorce papers come through, and Eileen realizes she is free to be with VP Murray, but their attempts are plagued with obstacles that make Eileen doubt her desires. Kenny tries to impress Brett by being a “bad boy” and gets a tattoo. Shannon puts out a petition to stop the dissection of frogs at school while Pat realizes that he needs to figure out how to be single again.