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.

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.

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.

Kenny’s jealousy over Brett’s relationship with his best girl friend leads Kenny to realize he’s been a bad friend to Allison. Jimmy and Shannon start their own ridesharing company. Meanwhile, Eileen and Pat are shocked to catch Clive “cheating” on them.

When Shannon asks VP Murray to be her godfather leading up to her confirmation, Eileen fears her own relationship with him might be moving too fast. Shannon’s big day also has a surprising effect on Kenny’s relationship when Brett says, “I love you,” sending Kenny into a tailspin. Meanwhile, the return of a hot former babysitter puts Pat and Jimmy at odds when she constantly makes passes at Pat.