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.

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 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.

Devastated by his break-up with Brett, Kenny tags along with Pat and Jimmy to a Lonely Hearts happy hour, but when they try to use Kenny’s sadness to get attention from single ladies, Kenny inadvertently steals the show. Meanwhile, Eileen shuns the usual Valentine’s Day traditions until a chance encounter changes her mind.

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.

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.

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”.

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.

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 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.

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.

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.

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

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.

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

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.

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.